The Heart Is The Bottleneck Praxis Volume 3 by Tiago Forte (Forte, Tiago) [PDF]

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The Heart is the Bottleneck

Praxis Volume 3 by Tiago Forte Copyright © 2020 Forte Labs, LLC

Dedicated to my brother, Marco, for persevering through the storm of personal growth, while serving and caring so deeply for people every step of the way

Table of Contents Foreword A Skeptic Goes to the Landmark Forum Trekonomics: The Economics of Post-Scarcity Why I’m Leaving Medium A Pattern Recognition Theory of Mind The Digital Productivity Pyramid The Future of Ebooks The Case for Digital Notes You Need a Budget: 13 Parallels Between Budgeting and Productivity The 5 Challenges of Becoming a Digital Nomad Emergent Strategy: Organizing for Social Justice The Essential Requirements for Choosing a Notes App as Your Second Brain A Maker’s Ethos in the Era of Networked Attention The Maker’s Guide to Content Curation The 7 Pillars of Content Curation RandomNote: Building an Idea Generator Desktop Zero: An Experiment on Clearing My Digital Workspace Tide Turners: A Workshop on Using Business to Fuel Spiritual Awakening A Productivity Expert’s Guide to Working with a Virtual Assistant About the Author About Praxis

Foreword Until 2018, my work was focused mostly on the mind – in my course Building a Second Brain, I teach people how to offload their memory and improve their thinking using technology. But what I’ve discovered is that there is a limit to how much you can expand your mind without also expanding your heart. When people focus only on their intellect, they soon plateau. The bottleneck to their performance then becomes their heart – their ability to tap into their emotions and hear what their intuition is telling them. Humans don’t think with their head, for the most part. Even the most rational, analytically minded people don’t make the important decisions using cold logic. We fundamentally think with our hearts, based on what intuitively feels right. This tendency has been treated as a weakness or a mistake. I hear of people trying to “correct” their cognitive biases and remove all emotion from their decision-making. But I don’t see it that way. The heart incorporates the emotions, which tell us so much about what really matters to us and what we truly want. The heart incorporates the body and its needs. The heart takes us out of the intellect that often limits our view, and into connection with ourselves and others. It is for this reason that the main theme of this book is personal growth – the expansion of the heart. The Heart is the Bottleneck chronicles my journey to understand the nature of personal growth. Through my own personal experiences as well as the works of others, I’ve sought to understand how it works without resorting to the religious, the spiritual, or the mystical. To frame it as a practical skill, that anyone can make progress on with time and effort. Personal growth is not normally thought of as a “skill.” But the world is now changing so fast and so unpredictably that it needs to become one. Our grandparents had one job for life; our parents had multiple jobs over their careers; our generation will have multiple careers. This demands that we learn how to grow not as a one-time event, but as an ongoing evolution of our identity.

As I dive deeper and deeper into the world of personal growth, I’m increasingly convinced that it is not a rare, exotic phenomenon only to be acquired via special seminars or psychedelic substances. Personal growth is everywhere, all the time. Life throws at us exactly the experiences we need to grow. Not because it is specifically looking out for each one of us, but because it throws everything at us. This implies that potential breakthroughs are everywhere. I read a book on meditation and there are stories of people getting past huge barriers and making a dramatic change. But I hear the same kinds of testimonials in books about tidying your house, and sailing, and writing, and fixing motorcycles, and almost every other topic imaginable. Mastering the mundane tasks of everyday life seems to be a gateway to living an extraordinary life. This book contains 18 in-depth essays previously published on the Praxis blog, edited for clarity and accuracy. They fall under five main themes: Personal growth In A Skeptic Goes to the Landmark Forum and Tide Turners, I describe my experiences taking part in intensive personal development programs, including what I discovered about myself and my past and how those discoveries impacted my work. In Emergent Strategy, I summarize my learnings from a book on social justice and movement building, and how I applied them to my teaching. And in You Need a Budget, I draw parallels between personal finance and personal productivity, including the growth mindset required to master both. Writing and note-taking I continue to be obsessed with the power of note-taking and writing to improve our thinking and change the trajectory of people’s careers. In Why I’m Leaving Medium, I look at the incentives and economics of modern blogging, and explain why they pushed me toward owning my own independent blog. In The Future of Ebooks, I speculate on what the future of electronic books could look like, if publishers embraced technology and online communities. In The Case for Digital Notes, I put forth my strongest argument for digital note-taking as a uniquely powerful category of software for enhancing people’s productivity. And in The Essential Requirements for Choosing a Notes App as Your Second Brain, I lay out the precise criteria I believe are most important in selecting an app for yourself. In RandomNote: Building an Idea Generator, I introduce a

simple web app we created to strategically inject randomness into your workflow by resurfacing notes from the past. Creativity and curation Zooming out a little, I also wrote about creativity, as well as the pre-cursor to creativity, which I believe is curation. The Maker’s Guide to Content Curation lays out a path for anyone interested in creating their own content, starting with curating the content of others. In The 7 Pillars of Content Curation, I dive further into the most effective principles for curators to follow to begin developing their own ideas and building an audience. And in A Maker’s Ethos in the Era of Networked Attention, I propose a healthier approach toward online media that frees us from the worst effects of information overload, by valuing creation over mere consumption. Practical guides I also continued exploring the practical aspects of modern work. In The 5 Challenges of Becoming a Digital Nomad, I explain what I believe are the five biggest practical challenges faced by anyone seeking to become locationindependent. In Desktop Zero, I present my findings from an analysis of the random files collected on my computer desktop over the course of a month, to determine whether it is worth sorting through and filing them. And A Productivity Expert’s Guide to Working with a Virtual Assistant contains my best advice on how to hire, train, coordinate with, and delegate to a virtual assistant your most common, routine tasks. Future speculation Finally, I allowed myself to speculate a little bit. In Trekonomics: The Economics of Post-Scarcity, I envision what a “post-scarcity” economy might look like, drawing on the Star Trek universe for inspiration. And in A Pattern Recognition Theory of Mind I summarize the scientific findings from Ray Kurzweil’s most recent book, and use them as a springboard to imagine the implications for my quest to build a “second brain.” I sincerely hope this book serves as a guiding light on your own journey of personal growth. I hope it shows that the smallest details of how you manage your daily work, when compounded over the years, have a profound impact on the trajectory of your career and life.

If you’d like to be notified when new essays are published in the future, subscribe to my free weekly newsletter. Every week I send out free interviews, in-depth essays, how-to articles, and other resources designed to enhance your personal productivity. And if you want full access to all my writing, consider becoming a member of Praxis. Thank you for being part of the community that allows these ideas to develop and spread. I’m forever grateful that I get to be the curator of ideas more interesting and powerful than anything I could invent myself. Tiago Forte Bacolod City, Philippines January 27, 2020

A Skeptic Goes to the Landmark Forum In September of 2016 I completed a weekend seminar called the Landmark Forum in San Francisco. It took three close friends, recommending it to me in three separate conversations, to get me there. I was very skeptical that a self-help seminar had anything to teach me, but decided it couldn’t hurt to check out one of the most popular training programs in the world. I have a training business, and I figured I could write it off as competitive research, if nothing else. My first experiences with Landmark were off-putting, to put it charitably. The people who greeted me the first morning were suspiciously happy. The marketing was comically corny, models in stock photos smiling back from shiny brochures. Walking into a room of about 150 people, I was greeted with the following statements written on a big poster: In the forum, you will bring forth the presence of a New Realm of Possibility for yourself and your life. Inside this New Realm of Possibility: — The constraints the past imposes on your view of life disappear. A new view of life emerges — New possibilities for being call you powerfully into being — New openings for action call you powerfully into action — The experience of being alive transforms I was confused. I’d never encountered so many words with so little concrete meaning. I wrote them in my notebook to decipher later. Despite the initial

worrying signs, I decided I would go along for the ride for three days and an evening.

Day 1 The first “distinction” (or lesson) we learned was “stories.” It’s a familiar concept — that we create narratives to explain our life experiences. And then we forget that we were the ones that created those interpretations, and we live as if they are real. These stories become the lenses through which we see, hear, and feel. Anything that confirms the story we latch on to as confirming evidence, and anything that doesn’t, we often dismiss. This pattern of seeing what we want to see and hearing what we want to hear is called having “blindspots.” What we miss because of our blindspots, we were taught, makes us suffer, holds us back from what we want in life, and suppresses our freedom, power, selfexpression, and peace of mind (the four benefits that graduates of the program have reported are the most impactful on their lives). As I said, it’s a very familiar concept. In fact, everything I heard in the Forum was familiar. I can’t think of a single thing that I hadn’t heard before in a book, a course, or a talk of some kind. But here is where Landmark is different — the conceptual lesson is just a starting point, not the main event. It is distilled down to the absolute minimum required to take action, instead of endlessly elaborated on. The Forum is designed to bring these concepts from “the stands,” where we sit passively as observers, and onto “the court” of our lives, where they become real. The facilitator invited participants to go up to the mic with questions, comments, and challenges, and the stories started flowing. I was struck by how easy it was for me to see the stories of others, and how apparently difficult it was for them to see their own. One woman had a story that her parents had abandoned her, working late every night at the convenience store they owned. After just a few gentle questions from the facilitator, she uncovered another perspective: that her parents had worked so hard for so many years only to provide for her and her sisters, who they loved more than anything else in the world. Committed to her own interpretation, she’d resented them for years. Besides the distance in their relationship, there was a clear impact on her: every time she was

on the verge of a promotion as an executive in the pharmaceutical industry, she pulled back, because “committing too much” to her work raised the specter of “abandoning” her own kids. Again and again, people revealed the powerful filters they had placed on their experience of life. One young woman sobbed as she recalled her father accusing her of shoplifting a small item at a grocery store when she was 9 years old. This one incident, burned in her memory as a child, outweighed years and years of her father’s care in her mind, informing her view of him as unloving and uncaring. In paired sharing, I talked to a young man my own age who had been the youngest of 9 children, and the only one who hadn’t been physically abused. His story was that of the survivor — that he didn’t deserve to be spared, and was somehow culpable for what had happened to his siblings. Even after a brilliant career at some of Silicon Valley’s most prestigious companies, that story weighed on him. He was still living out the self-sacrificial script of a martyr, trying to make up for an imaginary debt he thought he owed. We live our lives looking for evidence that our stories are true. We want them to be right more than we want to be free. More than we want close and intimate relationships. If the story is “I’m not good enough,” then we’ll either try a bunch of things, all the while looking for evidence that the story is true; or we’ll try nothing, assuming it’s true. In either case, the story is confirmed. By the end of day one, I was beginning to suspect I might have some stories of my own. Maybe.

Day 2 This period of my life was a hard time. After three years of self-employment, I had the business of my dreams. And the business of my dreams was failing. I had turned away from online courses after sales of my second course hadn’t even recouped the original investment. The “story” I had made up to interpret that experience was that “online teaching simply isn’t profitable.” And that it especially isn’t profitable for me. I began to pursue a series of other projects, taking on whatever I could to pay the bills. I started doing corporate training, which was more profitable than trying to sell directly to individuals online. The money was actually pretty good, and the clients prestigious, but it was missing what I loved the most — working directly with people on the real challenges in their lives, especially people that couldn’t afford high-priced consulting and training. I began to sink slowly into depression, using work to forget and to distract myself. I withdrew from my communities, from my friends, and even from my family, racing faster and faster toward goals I was sure would provide the satisfaction I was seeking. My health deteriorated, but I couldn’t find the motivation to change my lifestyle. I withdrew further, telling myself that I would return to my social life once things got better. I remember one day walking to a local coffee shop when the cabin fever of working at home got unbearable. Walking up to the cashier to order my drink, I felt an intense wave of anxiety, something I had never experienced before. I had become afraid of people. I had become afraid that someone would see how dysfunctional my life had become. I feared that they would point out what I deeply suspected — that I was a hypocrite, selling visions of professional success while my own life fell to pieces. So I worked harder. I did more research, put in more hours, polished every nook and cranny of my online presence to a bright gloss. As bad as it was, I couldn’t face the alternative: that my business had failed. It felt like if that happened, that I would have no future. If I turned away from what was supposed to be the pinnacle of success, I feared that the only option left to me was work that was less fulfilling, less interesting, and less rewarding. As you can probably tell, this was all a big story. Not the lived experience,

which was as real as anything. But the drama, the stark tradeoffs, the black-andwhite thinking. When life becomes dull, restrictive, and threatening you know you’re living in a story, not reality. I sat in the Forum looking for a breakthrough that would help me bring my business back to life. And instead, I got my father, front and center in my mind. I kept trying to push the thought aside. My relationship with my father was fine. Wasn’t it? And slowly, as we talked and shared, the layers peeled back. I had a story that I was uniquely messed up, because of how my father had raised me. He had been too harsh, too judgmental, had failed to listen and to support me growing up. Because of that, my story went, I couldn’t have the self-confidence, selfacceptance, and happiness I craved. This was, we soon learned, a “racket.” We blame others for things that happened in the past, making our case look as plausible and sympathetic as possible. We maintain lists of all the things our parents, our ex-s, our former friends, and our ex-bosses did so, so wrong. We collect mountains of evidence supporting these judgments. But we are always innocent in our stories, victims of their inexcusable behavior. The second distinction, of rackets, is that this blaming is often a pretense. It’s a way of concealing what’s really going on behind the scenes: we are getting a payoff. We get to be right (or make them wrong). We get to dominate them (or avoid their domination). We get to justify our behavior (or invalidate their behavior). We get to win (or make them lose). The ultimate purpose of a racket is to avoid responsibility. A man blames his ex-wife for the failure of their marriage. But it is a pretense to justify his own less-than-stellar behavior in the relationship. A woman blames her lack of decisiveness for her business troubles, but it’s a pretense to protect her from ever having to take a real risk, to put something on the line (yes, you can have a racket against yourself). A recent college graduate blames the job market for not offering opportunities, but it’s just a distraction from the lack of preparation he hasn’t taken responsibility for (rackets don’t have to be against specific people). By selectively inflating the wrongdoing of others, our own responsibility is diminished in comparison.

The way out of the racket, with its sweet, juicy payoff, is to clearly see the cost. There is always a cost — love or affinity, vitality or wellbeing, satisfaction or self-expression. The cost ultimately boils down to the experience of aliveness. Over time, the payoff gets less and less enticing, and the cost grows steadily worse. Eventually we become like drug addicts, giving away much of what makes life worth living to buy even the tiniest amounts of self-justification. I called my father, and followed the step-by-step format that we were coached through. I told him what I had been pretending: that he had “messed me up” and therefore my problems in life were his fault. I told him what that façade had been designed to conceal: that I had not taken responsibility for many areas of my own life, including my relationship to him as a son and a friend. I told him the impact this had had on me: hiding things in my life that I didn’t think he’d approve of, silently judging him because I didn’t think he could handle what I had to say, avoiding rooms he was in because I couldn’t feel at ease with him around. The impact was that I had nothing more than a “cordial” relationship with the most important and influential man in my life. I told my father that I loved him, with complete sincerity for perhaps the first time in my life. I told him that he had done a good job raising me into a man. And I thanked him for being the source of my life. Saying these words was incredibly difficult. I had to choke them out through tears. As I said what I had to say, I had a vivid image in my mind of handing over a giant treasure chest. My resentments and justifications stored inside like prized jewels. As I pushed it over, the chest opened, and there was nothing but trash inside. Saying what I had to say, it felt like a thousand pound weight being lifted off my chest. I understood at that moment the saying, “Resentment is like drinking poison and expecting the other person to die.” You don’t stop resenting for their sake. You stop it for your own sake.

Day 3 I’m not going to give away what happens on Day 3. I’ve tried, and it doesn’t make any sense without having lived it. What you learn in the Forum is a personal discovery, unique to each person, not a concept to be dissected and analyzed. By day three, you have the foundation and the language as a group to move at a breathtaking pace. The paradigm-shifting moments I had looked forward to having every year or two with my own efforts happened about every hour. I got clear that what was getting in my way was my constant desire to change. Trying to fix myself and everyone around me, I was blinded to how perfect we already are. Here and now, not someday or eventually. I got clear that the only constraints I face are the ones in my stories. And I am the one telling them. I am the source of the language that shapes my experience, which means I can change it. I get to say how my life goes, and what kind of life is available to me. Walking out of that conference room, I felt unleashed.

Day 4 I walked away from the Landmark Forum with a whole new relationship with my father as my biggest breakthrough. It’s been almost a year and a half, and it’s only gotten better since then. He’s no longer a threat to me, no longer an angry and closed-minded curmudgeon I have to contain and avoid. He’s a friend and a partner in life. We can tell each other anything, even on topics where we don’t agree. That would have been a pretty good result from a weekend, but what happened next took me by surprise. I went back to my business, and everything started going differently. Meetings I’d dreaded started turning into meaningful conversations. Conversations that I hadn’t known how to navigate started turning into opportunities. Opportunities that I hadn’t been able to see before started turning into projects. The lens I’d held up for my father had also been skewing my view of everyone else. I no longer sat down with an executive or manager already on the defensive, already expecting them not to like what I had to say. I actually started getting curious about what was going on over there, with them, instead of circling around my own head. I was able to see people simply as people, no better or worse than me, but with a need I could help with. Over the next few months, I rebuilt my life. I opened myself up to my communities, which had been waiting there all along. I expressed what I was going through to my girlfriend, my friends, and my family, who in retrospect, had always been listening. I looked at my business with clearer eyes, letting go of projects that I’d taken on to reinforce my ego or avoid failure. Landmark offers a whole curriculum of courses, on everything from communication to integrity to money to leadership. You get to choose your own adventure. A couple months later I took the Advanced Course, the followup to the Forum. While the Forum is about freeing you from your past, the Advanced Course has you design a new future. The day after I finished the Advanced Course, on Monday morning at 8am, I walked into a Whole Foods cafe in Oakland and wrote out a table of contents for a new course I had been considering creating. This was the future I had designed

in the seminar. It was to be a new, much bolder online course than anything I had done before, on note-taking and personal knowledge management. I could see now the limiting story that had kept me from getting started on it: that my success depended on me doing everything perfectly. This story had me endlessly revising and polishing my writing and my products, never convinced that they were quite good enough. It had me doing every last little thing myself, not asking for and sometimes even refusing offers of help (“They won’t do it right”). I had the experience of working harder and harder to try and “catch up” to an impossible standard I’d set for myself, but feeling like I was falling further and further behind. The piling debt and unpaid taxes weren’t the worst consequence of my unyielding perfectionism — it was the experience of myself as constantly stressed, anxious, self-critical, and resigned that it would never change. I decided to write a new story for myself: that I could work closely with others, with all the vulnerability, risk, and messiness that entails. I decided that people would no longer be threats to me, but rather the most precious opportunities in my business and my life. I got to work on my new course that day, but in a completely different way than I had before — holing up for weeks and weeks of solitary work confined in my apartment. The first thing I did was ask 10 of my closest followers to work with me to develop it, meeting with me for 1 hour every week for 6 weeks. Each week I would concentrate on producing just one unit of material, and showing it to them for feedback. The perfectionism that had kept content development clenched tightly in my iron fist was, simply, gone. Those six weeks included some of the most gratifying, collaborative conversations of my career. Even after 6 weeks, I only got to about 50% completion. There were too many unknowns to be able to make all the decisions upfront, and I needed to call on another group for help. I decided to start selling the course before it was finished, and at a price ten times the usual one: $500 instead of $50. I remember sitting at my computer as sales began, terrified that no one would even visit the page, much less pay me that much money for an incomplete product. But 50 people took a bet on me. With their help, I completed the course, finalizing each week’s content based on their real-time feedback. I was open and transparent about what was missing and where I wasn’t sure. And not only did I not die from revealing something imperfect — my customers unanimously

agreed that “seeing how the sausage was made” taught them as much as the course itself. I’d discovered a new “way of being” — connected, vulnerable, fearless, generous. And that is far more valuable than any habit, tactic, or framework.

Today That new future has become my present. I did three more cohorts of the course, making huge improvements each time. I hired a course manager and later, coaches, making it into a world-class training program for a new way of working. In 2017 I nearly quadrupled the previous year’s income, while having far more fun, making many new friends and collaborators, and staying connected to my body, my communities, and my purpose in the world. One year later, Building a Second Brain has become a movement. We launched a self-paced version, which will allow many times the number of people to learn the material. I have an editor, a lawyer, and a group of reviewers supporting me as I turn it into a book. I work with a decentralized, remote team of 4 outstanding people, driving toward our goal of transforming how people work. How can I explain how all this happened? I had all the content, all the skills, all the tools, all the contacts, and all the knowledge I needed. There was no fundamental insight I had to have, or new framework with step-by-step instructions. The Forum isn’t about giving you something new — it’s about taking away what’s in the way. I’ve become a passionate advocate of the work that Landmark is doing. I know of nothing that comes remotely close in its ability to change lives in so short a time. About a dozen of my friends and family have taken it since then. Everyone has come back to thank me for sharing with them one of the most meaningful experiences of their lives (especially the skeptical ones). The people I’ve met there have become some of my closest friends, and more recently, collaborators. I’ve seen personal miracles time and time again, from nothing more than having conversations about our lives and what’s important to us. I’ve had to question everything I thought I knew about humans, and how much they can change in how short a timeframe. That questioning has been challenging at times, but it has left me with a vastly expanded sense of what is possible. I’ve waited a long time to write about my experiences at Landmark. The ones I’ve included here are just a drop in the bucket. I waited to tell this story because I wanted to see if the results would last. I wanted to be sure it wasn’t just a temporary emotional high before putting my reputation behind it.

At this point, I am absolutely convinced that it works, that it lasts, and that this is some of the most important education going on in the world today. I recommend the Forum above my own courses and programs. The ability to see past your own interpretations and take full responsibility for your experience are absolutely fundamental to changing how you work, but go far beyond productivity. The work that Landmark does enables so many kinds of learning, growth, and change, my own work included. There are a lot of personal growth experiences I’ve benefited from. But making a real impact on this world is going to require something different. Most people can’t take 10 days off for a silent meditation retreat, or spend thousands of dollars for a week at Burning Man. Most will not go on Ayahuasca excursions in Peru or float in sensory deprivation immersion tanks. Those are priceless experiences, but we need something more integrated into daily life. Something that happens in normal, everyday conversations and relationships, and that we can participate in after work and on weekends. And that is the Landmark Forum. The best way to see what the Forum is about is to attend a 3-hour introduction. Visit this page for more information and to find local times and addresses. I especially recommend attending a “Special Evening,” a larger introduction led by a Forum Leader periodically in major cities. These sessions are facilitated by the people who actually lead the Forum, and use many of the same formats and distinctions, so you can get a sense of what it’s like. Note: The views expressed on this blog are my personal views and are not the views of Landmark Worldwide.

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Trekonomics: The Economics of PostScarcity I recently finished listening to the audiobook of Trekonomics: The Economics of Star Trek (Amazon Affiliate Link), by Manu Saadia. It was probably the most fun I’ve ever had thinking about economics, due to the outstanding premise: What if we treated the Star Trek universe as if it was real, and used it to draw economic lessons about post-scarcity? The model rests upon one glaring, unavoidable fact of the Star Trek economy: there is no money. There are a few mentions of “exchanging credits” in the TV series, but they all prove to be metaphors, throwback rituals, or jokes. No money means no salaries, no revenue, and no profit. The great majority of the machinery by which capitalism runs is simply gone. The main reason there is no money in Star Trek is due to the existence of replicators: common household appliances that can produce virtually anything on demand. Just search through the database of product designs, push a button, and the item you desire will be fabricated, whether it’s a sandwich, a pair of shoes, a hammer, or a diamond. The existence of replicators means there is no scarcity. And scarcity is the fundamental fact of capitalism: it’s impossible to charge money (much less, a lot of money) for something that anyone can fabricate for free at home. Without scarcity, we no longer need the invisible hand optimizing the allocation of scarce goods. Supply and demand lose all relevance. But just because there is no money, that doesn’t mean there is no capital. We are used to denominating capital in terms of currency, but there are other forms it can take — tools, machines, and knowledge. Capital is any productive asset that allows labor to turn raw materials into finished products. Already today, estimates by economists indicate that the value of human capital in the economy– the knowledge and know-how stored in human brains – dwarfs all other forms of capital. In the United States, the value of human capital is five to ten times larger than the value of all physical capital combined.

Replicators change the nature of capital, which changes the nature of ownership. With replicators, ownership doesn’t yield exchange value. Just because you own something, that doesn’t mean you can benefit from selling it. You may have a replicator in your home, but you didn’t purchase it, and can’t use it to sell products at a premium. It doesn’t save you or make you money. Because again, there is no money. Since you don’t derive any excess wealth from your home replicator, what is the point of owning it? Ownership means you are responsible for its operation and maintenance. Ownership thus implies service. It actually becomes illogical and inefficient to take the weight of ownership on your shoulders. We are already seeing the beginnings of this today: the sharing economy makes it easier to access cars, bikes, houses, tools, and equipment than to own them. And this is revealing just how much of a burden it is to own, manage, store, and maintain these things if you don’t have to. The central defining question of a post-scarcity economy is: why work? When work is decoupled from bio-physical necessity, what’s the point? The goal of work in the Star Trek universe is to fulfill the deepest needs of human nature: belonging, love, recognition, purpose, and self-expression. Labor, leisure, and art merge together and become just different flavors of learning, making, and sharing. The purpose of work is to find and express your purpose. As an example, the family of Captain Jean-Luc Picard owns an ancestral house and vineyard back on Earth, but they are more like family heirlooms to be treasured, rather than productive assets to be maximized. The property is of immense sentimental value, even if its economic value is negligible. How could such an economy actually work? The currency that still matters in a post-scarcity economy is reputation. Beating your competitors, producing artistic or scientific breakthroughs, and being known and respected are the greatest rewards. Because even when you have a replicator that can produce anything, one thing remains scarce: positions of authority, leadership, and respect. There is only one Captain Picard. This too is happening today. Gloria Origgi, an Italian philosopher and researcher, argues that the overabundance of information produced by the Information Age is ushering in the “Reputation Age.” We rely on the opinions

and judgments of people we respect to tell us what to think and believe on topics too numerous to research ourselves. The main filter for which opinions to listen to is one’s reputation, which acquires a tremendous power that money can’t buy. What’s so enticing about this scenario is that reputation preserves the upsides of money — the ability to exchange value and show appreciation — while eliminating its downsides. Reputation is inexhaustible, non-rival, nonexcludable, incorruptible, freely given, and freely taken. You can’t bribe, cheat, steal, or force your way into a good reputation, and attempting to will only make your reputation sink lower. In a reputation-based economy, meritocracy is the highest ideal. The integrity of reputation rests on the foundation of equal opportunity. That’s why any form of “stacking the chips” (such as genetic engineering) is strictly prohibited in the Federation. Having genetically enhanced humans would probably produce a lot of value for society, but it would also distract us with a genetic arms race. With reputation the highest prize, Star Trek society funnels far greater resources into science and research. The problems to be solved and products to be created wouldn’t be only the ones that produce the most profit, but the ones that are most important and respected. That is, the most complex and risky Grand Challenges. The Federation is able to throw massive numbers of people at any problem, because the supply of trained people is not constrained by poverty or accidents of birth. But it’s not only large scientific enterprises that will benefit. Consider even a small business: it doesn’t have to deal with the biggest cost, labor, because there is no money to dispense. Employees are self-selected for their passion for the craft, since there’s no other incentive to work. A store with a strong reputation will attract the best employees, which will cause it to earn an even better reputation, and so on, in much the same way money allows today. While services, which can always benefit from a human touch, will thrive, that doesn’t mean no work will be required for products. But that work will move from retail, wholesale, distribution, storage, shipping, supply chain management  — all automated by machines — to the design of products. Human design and scalability are not at odds, after all. Anything that involves even a small touch from a human acquires tremendous worth, even if reproduced endlessly. Like a Beatles song produced from a stroke of genius, and today residing on millions of devices around the world.

The determinants of value for a product will no longer be scarcity or utility. They will be affect, sentimental taste, personal idiosyncrasies, and craftsmanship. We will need to figure out how to preserve these qualities even as our products become digital, streamable, and copyable. The biggest challenge for every Federation citizen is not how to survive, how to protect their property, or how to make ends meet. Their challenge is how to allocate their time, talents, and capacity for empathy to best contribute to the common wealth. Developing themselves thus becomes inseparable from developing as a civilization.

The rationalization of knowledge work This book shed some light on a paradox I’ve been thinking about: I advocate for creativity and artistry in knowledge work, and yet much of my work seems to be “automating” knowledge work. I seem to be standardizing the ways in which we read, capture ideas, summarize them, organize them, annotate them, and retrieve them. Saadia observes that these are not at all at odds, but necessary for economic evolution. Agriculture once took the vast majority of humans’ time and energy. Today it makes up a tiny percentage of our economy (1% in the U.S.) and workforce ( Collection Habit Clarify => Next Physical Action Organize => Project List Reflect => Weekly Review Engage => Contexts/priorities These habits allow the principles of task management to recede into the background, taking up less and less attention over time. By understanding the basic principles, we can find original, creative ways of customizing them to suit our individual needs and preferences. Level 3 includes not just forming new habits, but extinguishing or adjusting existing habits. This requires examining underlying personal narratives,

incentives, and patterns that drive our behavior, using psychological and design techniques to reimagine them. We lead people through this process in our online course Design Your Habits.

Level 4: Personal Knowledge Management (PKM)

Includes: Progressive summarization PARA Workflow Strategies Whereas Level 2 is about taming the flow of information related to actions, Level 4 is about the flow of knowledge. Personal knowledge management (PKM) is a set of skills and tools for an individual to capture, organize, and deploy the knowledge they accumulate while completing their work. It draws from diverse fields such as digital archiving, process design, and project management, and includes software programs for ereading, digital note-taking, word processing, cloud storage, and others. Personal knowledge management is the topic of Building a Second Brain, our online course in which we help people unlock their creative potential using digital note-taking software.

Level 5: Just-in-Time Project Management

As working professionals, we don’t have time to consume a body of knowledge upfront and then regurgitate it for a test, as in school. Professional education has to take place right alongside daily work. We have to build the plane (and learn to fly it) as it’s taking off. For PKM to be sustainable, it needs to directly enable the execution of real projects. That’s why Just-in-Time Project Management is the capstone of the Pyramid. The knowledge we are collecting and managing needs to have an immediate return to be justified, instead of only far in the future. While you don’t need to build levels 1-4 before starting to work on real projects, the scale and ambition of the projects you can successfully execute is constrained by the structural integrity of your Pyramid. The taller the edifice you want to erect, the deeper and stronger your foundation must be.

The Next Frontier We are hard at work on the next frontier – making Just-in-Time Project Management as coherent and teachable as the other topics. Read Tiago’s series on Just-In-Time Project Management for the latest developments.

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The Future of Ebooks I’ve published a few ebooks over the past few years, and have plans for more in the coming years. In contrast to fears about the “end of reading,” my selfpublishing experiences have led me to believe that we’re in the midst of a transformational revolution in reading. But it remains to be seen whether ebooks in particular will fulfill their potential in the digital age, or remain a lackluster experiment. In this article I’ll examine the promise and potential of the modern ebook to try and see where we’re headed.

Context over content The first trend that’s becoming clear is that content is increasingly a commodity. With ever-greater volumes of every kind of writing – articles, social media posts, blog posts – being created every year, with instantaneous global distribution via the Internet, any business model based on content scarcity will no longer work. As the emphasis shifts to discoverability amidst an endless sea of content, the focus for both publishers and consumers is moving to the context surrounding the book.

The context of a book – the metadata that describes what it is, what it’s related to, what others are saying about it, what it means, how it’s structured, how it was conceived, and countless other characteristics – has become paramount. Because without metadata, a book is invisible. In the physical world, a lot of this context came “built in.” Bookstores, booksellers, librarians, and reviewers provided commentary and direction to help us find what we were looking for. The tiniest details of a book’s size, shape, cover design, title, inside flaps, and placement in the store gave us rich contextual clues. But in the digital world, a lot of that is stripped away. There is no chance that

you will serendipitously come across a book on the shelf, in the aisles, or at a coffee shop being read by someone else. You can be looking over someone’s shoulder as they read their Kindle and still have no idea what they’re reading! The signposts and markers of what is worthy of our attention have instead been funneled through personalized algorithms online. But algorithms cannot capture every possibility of what we might benefit from reading. The challenge of digitizing books has never been the text conversion process. That is trivial. The hard part is rebuilding the socio-cultural context that used to so strongly shape our reading habits. Online marketing funnels, recommendations from friends, top seller lists, and other promotional tools have arisen to meet this need, but they don’t quite integrate into our daily lives as seamlessly. Looking at new media and social networks, we get a strong picture of what context-first content looks like. Fledgling media startups start with context, asking where and why and how a person might want to consume media, and then they work backward from that to create the perfect product and environment for it. Snapchat developed disappearing selfie videos to meet the needs of teens seeking low-cost self-expression, while retaining their privacy. The recently announced IGTV is specifically designed for long-form, vertical video, capitalizing on the ease of hitting “record” on smartphones, while still giving video producers exposure through the Instagram network of 1 billion users. While old-school publishers think of the internet as a new means of distributing the same old text containers, and software as a way to drive down costs, startups are building new kinds of content that couldn’t previously be conceived of. For them, text is just one possible output, not the only possible one. What might it look like to create ebooks that focus primarily on adding context around the content? Here’s some of my favorite ideas I’ve come across: Show a heat map of the text, going beyond Kindle’s “most popular” passages to show the most hated, the most disagreed with, the most impactful, and other filters Allow readers to curate whose highlights they see: their friends,

their neighbors, their colleagues, or influencers they follow in the same field Reveal data about the behavior of other readers (not just average reading time): How far does the average person get before giving up? How many notes do they take on each chapter? How many passages do they highlight? Which chapters do they come back to reference the most? Which passages are copied the most? How many people have clicked on each link? Enable deep linking from the web into specific chapters, passages, or sentences, allowing visitors to see a short preview of the pages before and after, and purchase the book if they want to read more (this preview feature is akin to Amazon’s Look Inside, but with links) Make the references and bibliography more interactive, allowing sorting by importance, relevance, date created, or other criteria for those seeking to dive deeper into the source material Reveal the writing process, including early sketches, a changelog, or editor’s notes, for those interested in exploring how the book was created Create tagging systems, either for idiosyncratic individual use or collective collaboration, to allow humans reading the text to add labels and hooks of semantic meaning for themselves and others Digitizing text created great abundance. It is metadata, and the sorting, filtering, and searching it enables, that will help us make sense of it all. Metadata is the lens that makes our choices about what to read meaningful.

Service over product If you zoom out from the ideas above, a new definition of “publisher” starts to come into focus. Publishers are no longer product companies. They are service companies. What matters is not the container wrapped around a bunch of exclusive text, but the service wrapped around the container. Context is paramount, but it takes a lot of work to organize and deliver it in a user-friendly way.

This is happening across the media landscape. Take iTunes as an example. If content was truly differentiated, the amount you paid would vary a lot based on quality. But it doesn’t. Every song costs 99 cents. The only reason people would pay the same amount of money for goods of vastly different quality is if it isn’t the product that matters, but the service that iTunes provides: on-demand listening across different devices. The Kindle store has grown to dominate the ebook publishing market by offering a similar service: on-demand reading on any device. You don’t have to worry about where to buy it, how to get it, or where to store it. It’s essentially streaming for books, even if you never sign up for Kindle Unlimited, their allyou-can-read service. The book appears when summoned, and Amazon takes a minimum 30% cut to ensure the stream never gets interrupted.

What are the services that readers want around their books? They want convenience, specificity, discoverability, ease of access, and connection. In a world where e-reading devices are ubiquitous, e-reading software is free, storage is plentiful and cloud-based, and any kind of content can be distributed everywhere at the push of a button, it is these value-added services that will define what is worth paying for. Publishers need to realize they are no longer in the content production business. They are in the content solutions business. Their books need to become part of a value chain that solves their customers’ problems. Because what people ultimately want is not a book. They want an answer, a pathway, or a spark of insight that leads them to an outcome or experience. This implies a 180-degree pivot in how they treat their content. Instead of locking down written works with expensive and complicated DRM, publishers should adopt open, accessible, interoperable standards. They should use as much of the content as possible to build up context, and then use that context to promote discovery. Instead of competing on cost in a market that has zero costs, they should actively encourage every kind of reuse of their intellectual property. The publishers that win in the digital age will be those that offer metadata and tools that help their readers manage the true enemy of reading: the curse of abundance.

Creation over consumption Underlying both of the trends above is a deeper one: people are moving from passively consuming content, to interacting with and creating it. It now feels strange to many of us to sit on the couch and watch a TV show from beginning to end. What feels natural is to have our phone in front of us, posting on social media, commenting on others’ posts, and looking up actors, characters, and explainers. In a way, this has always been true. Books have always called out to be annotated, marked up, underlined, dog-eared, summarized, cross-referenced, shared, loaned, and talked about. From the very beginning, books were social objects, pulling into place around themselves everything from book fairs, to book clubs, to writer’s circles, to conversations around the water cooler. What’s changed is that all that marginalia – the bookmarks, notes, highlights, progress markers, reviews, comments, discussions – once hidden amidst the pages on each of our private bookshelves, has been published and networked online as digital artifacts. They reflect an individual’s preferences and intentions and take significant human attention to produce, which makes them valuable. In isolation, they are valuable to ourselves and perhaps our closest friends. At scale, the patterns they contain hold immense value as signals of insight, quality, and buying behavior. Readers today expect to be able to “look under the hood” of a piece of content they’re consuming. They expect to be able to leave impressions on the medium, pushing and pulling and capturing the parts that resonate the most. For the works we fall in love with, we want to see how the sausage is made, so to speak, like watching the outtakes or director’s commentary for a movie. Forward-looking publishers will begin to provide richer forms of interaction: Exporting individual metadata, like highlights and notes (going beyond the rudimentary export options currently offered by Kindle and iBooks to include images, different formats, and different destinations) Forking or editing the story (like video games or “Choose Your

Own Adventure” stories) Adding your own interpretation or expression (like adult coloring books, which have soared in popularity in the last few years) Mixing and matching pieces of content to create your own works (like Instagram Stories, or textbooks that allow professors to curate exactly the sections and chapters they want, to be printed on demand) Centralize discussions around the book (on Amazon or Goodreads even), with strong tools for surfacing the most useful or insightful comments and reviews Make ebook formats more HTML-compatible (EPUB, the most common format, is already just a specialized type of webpage), which would allow multimedia embedding and other sophisticated features Include appendices or links to primary source material, deep dives on ancillary topics, and bonus extras like interviews or study guides, either free or paid This level of interactivity might seem challenging, but it’s been done before. ChessBase is a database and book engine used by serious chess players around the world. Both ebooks (by multiple publishers) and mobile apps integrate directly with the database, which contains thousands of historical and modern games that can be searched and replayed. It includes a chess-playing engine so players can “step into” famous matches, allowing them to test their skills against the likes of Bobby Fischer or Garry Kasparov. It goes even beyond that, allowing players to author their own ebooks in EPUB and MOBI, including things like chess positions and tactics puzzles, from within the same interface. Although there is clearly quite a bit more to ChessBase than an ebook, it points a potential way forward: ebooks as just one entry point into an ecosystem of content, services, apps, trainings, communities, and other products.

Streams over containers At the heart of our desire to create is connection. As sublime as the creative process can be, what we’re truly after is what it evokes: surprise, delight, gratitude, insight, or revelation in another person. A reaction of any kind, really. This too has always been part of the experience of reading. There is something special about meeting someone who has read the same book as you. You have something in common, something shared. The most mundane aspects of publishing, like taking pre-orders or posting a review, become special moments of contribution and belonging for the community that has gathered around an author.

Finding and downloading a book is easy, but getting it attention is harder than ever. This means that the network around a book will grow in importance, because without it, the book will never be discovered. And there’s no reason that this network should limit itself to “post-publication.” In fact, there is no such thing as “post” anymore. A book is a continual process of research and refinement, and readers have been injected much earlier into that process than ever before. Books have been crowdsourced and crowdfunded, collaboratively edited, published one chapter at a time, and made into interactive webpages. The book

is really just an excuse to form a community, which provides not only a prequalified market of committed readers, but a tribe of evangelists and promoters in the all-important channel of word-of-mouth. It has become clear that the book is more of a social artifact than ever. The point-in-time contents inside a black-box container has been unfurled into a stream – an ever-changing conversation around the book, what it means, and why it matters. Time itself starts to become an essential ingredient in the writing – when and how often you engage influences your experience as much as the text itself. Like Wikipedia, what’s most interesting is not the article itself, but the talk page, where the community hashes out its priorities and conflicts. The work’s authority comes from its responsiveness and shared intent, not its preciousness. Imagine a future where instead of lending someone a book, you lend them your bookmarks – the notes, annotations, and references you’ve added. What you are really sharing is a collective conversation, the cumulative strata of many layers of marginalia built up through the skillful application of attention. By connecting these small, local networks forming around each book, we could eventually create a single networked literature. Such a macronetwork would allow us to trace the source of any idea, concept, or influence through time. As Kevin Kelly puts its, “we’ll come to understand that no work, no idea, stands alone, but that all good, true and beautiful things are networks, ecosystems of intertwingled parts, related entities and similar works.”

Ebooks as digital artifacts Streams are powerful, but they underestimate the value that humans place on tangible artifacts. This is true more broadly of all things digital. As everything gets turned into a streamable, on-demand monthly subscription, we are beginning to realize that the “things” we once surrounded ourselves with served purposes beyond pure utility. As more and more of our lives take place online, there’s a growing disparity between our experiences, and the records of those experiences. The “souvenirs” that naturally accumulate in the real world aren’t guaranteed in the digital world. Data gets lost, devices get stolen, and photos and songs get trapped in obsolete formats. These souvenirs once functioned as touchstones, memory aides, and visual quantifiers, reminding us serendipitously of who we are and where we’ve been. The blessing of digital reading is also its curse – it is traceless. What came of those hours of precious attention we spent immersed in the mind of another? What did we take away from the experience, besides a warm fuzzy feeling of edutainment? The hunger for artifacts will ensure that printed books continue to survive far into the future, and other more whimsical efforts like Bookcubes can help fill in the gaps. But the more fundamental need to take away something tangible from the experience of reading is one of the things driving the return of commonplace books – personal, curated collections of facts, insights, musings, quotes, and research originally invented in 19th century Europe as a way to deal with the information explosion of the Industrial Era.

5: Lewis Carroll’s commonplace book, showing his musings on ciphers and detailed handwritten charts exploring labyrinths

My online course Building a Second Brain is about how to create a “digital commonplace book,” meeting the need described by Craig Mod: “There is a gaping opportunity to consolidate our myriad marginalia into an even more robust commonplace book. One searchable, always accessible, easily shared and embedded amongst the digital text we consume. An evocation — the application of heat to the secret lemon juice letter — of our shared telepathy.”

The book will endure Considering all these major changes, I believe that books will endure. Publishing isn’t unprofitable; it’s unprofitable to use expensive production techniques for a single use and a single format. The field of technical writing has long offered a solution: single-source databases with multiple output capability. This is exactly how the Internet works: Yelp keeps all its data in a database, whose contents can be served up to any number of devices in just the right size and shape desired. The risk of not publishing content in open, accessible formats will grow as the number of opportunities for reuse grows. Kevin Kelly defines the book nicely: “A book is a self-contained story, argument or body of knowledge that takes more than an hour to read. A book is complete in the sense that it contains its own beginning, middle, and end.” This definition starts to boil it down to its essence: a book is now best understood as a concentrated unit of attention. Facts are useful, ideas are interesting, and arguments are important, but only a story is unforgettable, life-changing even. Only stories reach through to our empathy and our humanity, allowing us to walk a little in someone else’s shoes. To the extent that the grand challenges of our time require us to come to mutual understanding, and I believe they absolutely do, the book will endure as the minimum amount of concentrated attention required to become immersed in a story. What a book transmits is not just information, but imagination. By crystallizing our ideas in the form of text, they take on a form that can survive years, decades, even centuries. Books free us from the bounds of time, like interstellar spaceships prepared to travel light years to find a suitable home. I drew heavily on these sources for this article, but the ideas got too intermixed and intermingled to cite directly in the text: 1. Embracing the digital book, Craig Mod 2. The Technium: What Books Will Become 3. Why Information Grows tweetstorm

4. Book: A Futurist’s Manifesto: A Collection of Essays from the Bleeding Edge of Publishing

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The Case for Digital Notes In our course Building a Second Brain, we teach people how to capture, organize, and share their most valuable knowledge and know-how using technology. We call this practice Personal Knowledge Management, or PKM.

6: The 3 stages of Personal Knowledge Management

One of the most common questions I am asked is “Why digital notes?” This article will explain why, out of all the kinds of apps out there for managing knowledge, I recommend the category of “digital note-taking apps.”

The Case for Digital Notes There are many kinds of software you could use to store and access your personal knowledge. Each one is best used for a specific purpose: Word processing apps (like Microsoft Word) are best when you need special formatting or printing options Social media apps (like Facebook and Twitter) are best when you want maximum social engagement Cloud storage services (like Dropbox, Google Drive, or iCloud Drive) are ideally suited to sharing or accessing your files on multiple devices Collaborative editing apps (like Google Docs) are best for real-time collaboration While all these categories have their uses, there is really only one category of software I can recommend as the centerpiece of your Second Brain: digital notes apps. Popular options include Evernote (iOS, Android, Mac, Windows, browsers), Microsoft OneNote (iOS, Android, Mac, Windows), Simplenote (iOS, Android, Mac, Windows, Linux), Google Keep (browsers, iOS, Android), Bear (Mac, iOS), Zoho Notebook (Windows, Mac, iOS, Android), Notability (iOS, Mac), Goodnotes (iOS), and many others. Digital notes might seem a strange choice at first. How can something as lofty and grand as a “second brain” be created with something as mundane as “notes”? I believe that notes are the best metaphor for how we think about our personal knowledge. Unlike other common terms like documents, files, entries, cards, or records, notes have a natural home at the heart of our creative process.

Notes are personal, informal, quick and dirty. They are not for public consumption, but for your own personal use, like a leather notebook you keep in your backpack. Notes are open-ended and never finished. “Taking notes” is a continuous process, in which you can noodle on ideas without an immediate purpose in mind. Notes have low standards for quality and polish. They are easy to jot down, because it’s fine if they are messy, incomplete, or totally random. Notes naturally mix diverse types of media. Just like a paper notebook might contain drawings and sketches, quotes and ideas, and even a pasted photo or post-it note, notes naturally combine different kinds of media in one place. Digital notes apps give us the most important benefits of technology – searching, sharing, access on multiple devices, backups, editing, meta-data, linking, copyand-paste, and many others – while avoiding complicated data entry.

Your Home Base There will always be times and places to use specialized apps, including all the other apps for managing information I mentioned previously. The point of centralizing your knowledge management in one app is not to stop using all the others. It is to give you a secure “home base” that you know you can always come back to.

7: Your Second Brain is a universal inbox and home base where you keep the knowledge most important to you

Because the strength of a notes app is saving content from a wide variety of sources, it can function as a “universal inbox” for capturing any kind of information coming your way. By having a home base that you know you can always depend on, you’re free to strike out towards the frontier of knowledge, and experiment with the most cutting-edge new apps. Your home base should be stable, secure, and not make any dramatic changes. This is why it’s important to have a popular, well-supported app as the centerpiece of your Second Brain. You are free to try out any fancy new app as an experiment, but it’s important that your primary platform won’t suddenly go out of business.

Joining a Community The next important factor to consider is that, when you invest in a notes app, you are joining a community. This isn’t true of most other apps you use. I don’t think many customers consider themselves a part of the “Microsoft Word community” or the “Dropbox community.” Information management apps tend to be utilities. It is obvious how to use them, which means you don’t need much context or training to learn how. But notes apps are different. You can download and install one, but it isn’t at all clear how you should use it. These apps are like blank canvases, allowing many possible uses and many possible approaches. This can often be a major hurdle for a novice, but presents a wonderful opportunity if you’re willing to invest some time. You can use it any way you want, to exactly suit your needs. Because notes apps can be customized to your needs, they quickly occupy a uniquely personal place in your digital life. They are the earliest stage of your creative process, when your ideas are only half-formed, and your subjective observations are mixed in with your research and record-keeping. Many users of these apps quickly find that they become a part of a community around the app they choose. Whether or not you join a Facebook group or register in their user forums makes no difference. You are part of their community, because everything they do has a dramatic impact on how you work. Every feature they release, every change they make, every change of direction will impact how you work to a greater extent than other categories of productivity apps. This is why you should spend some time getting to know their culture: How do they think about the purpose of their product? What are their beliefs toward privacy, security, and customer support? What is their origin story, their core beliefs, and their long-term outlook?

All these things are worth considering when you will potentially invest years of effort into building your knowledge library on their platform.

Common Pitfalls I’d like to point out a few of the most common pitfalls I often see people succumb to as they search for the perfect knowledge management app. Switching frequently between apps There is a “shiny new thing” syndrome especially common to people who love technology. Every year new apps come out, launching with slick marketing campaigns and bold visions. It is tempting to view each new product as a silver bullet, trusting that a team of crack engineers and designers has somehow “solved” knowledge management once and for all. As you can probably tell, I don’t put much stock in these hopes. There is a cost to switching apps, and I think it’s much better to invest in a trusted solution than to spend energy migrating from one place to another. What really matters is your output: what are you creating or producing out of this knowledge to make a difference in your career, your business, or the world? It’s doubtful that any mere feature set will dramatically improve the results you’re getting. My recommendation is to instead pick one notes app, and invest in it for the long term. Building your own I live in Silicon Valley amongst a lot of talented software developers, so perhaps I see a disproportionate amount of this. But it’s very tempting for people who know how to build (or piece together) software to throw aside the available options, and set out on a glorious path to creating the “one perfect app to rule them all.” Don’t do it! In almost all cases, that path leads nowhere. At best, it becomes a passion project that only works for one person’s idiosyncratic methods, slowly decaying over time as the technology gets old. That time and energy is much better spent creating things and solving problems. Notes are a means to an end, not an end in themselves. My recommendation is to instead use a popular, off-the-shelf app that has most, if not all, of the features you need. Trying to find one app to do everything

It’s tempting to look for one app that can do everything. This most often results in one of the two pitfalls described above. But there is no universal app. I often simultaneously use Asana for managing projects, Google Docs for shared brainstorming, or Mindnode for mapping out new topics, for example. The job of your notes app is as a storage location of last resort. If your knowledge is better suited to a specialized app, by all means, keep it there. But if you complete a project or stop using one of them, be sure to bring that content back into your notes as a record of the work you’ve done. My recommendation is instead to always use the best tool for the job, but at the end of the day, save everything you want to keep to your notes app. Focusing too much on the long term As important as it is to preserve your notes over the long term, this can also become a pitfall. I’ve seen people spend so much energy creating multiple, totally secure backups, or using file types that will never change, that there’s no energy left over for creating! Remember that all this work is designed to make it easier to produce meaningful results. Don’t make a hobby out of engineering a system so resilient that it can survive a nuclear war! My recommendation is instead to balance short and long-term perspectives, prioritizing doing good work in the medium term of the next few years. Waiting until you have the whole system perfectly figured out to get started This is perhaps the most common one, and the most problematic, especially among perfectionists. It’s understandable to feel anxiety and fear when embarking on such an important undertaking. It’s so tempting to try and have all the details perfectly worked out before you take the first step. But ultimately, you can’t know exactly what will work upfront. An approach that works for someone else may not necessarily work for you. Even this one. The only way to build a Second Brain is to start small, and make incremental improvements over time. Trust yourself that you will learn and grow right alongside it.

Do What Works I’ve presented my strongest opinions and recommendations based on my experience, but what ultimately matters is that your approach works for you. A notes app is a blank canvas, just like a brand new leather-bound notebook. It offers endless possibilities for those willing to experiment. But its ultimate purpose is to empower you to imagine, to create, and to take on creative adventures. I encourage you to leverage technology to its maximum potential, but to remember at the end of the day that your creativity is the only irreplaceable piece in the whole system. Do what works for you.

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You Need a Budget: 13 Parallels Between Budgeting and Productivity I recently read and took notes on You Need a Budget (Amazon Affiliate Link), a popular book on personal finance and budgeting (with accompanying software for managing budgets) by Jesse Mecham. My interest in this book is three-fold:

1. I’m terrible at budgeting and need help 2. I want to borrow principles and methods for managing money to help people manage their time and productivity

3. YNAB has built an incredibly strong brand and community, and I want to learn from them as I write my own book As I read and digested the YNAB approach to personal finance, I began to sense a deep connection to principles of productivity. I’ve concluded that there is a series of fundamental mindset shifts required to manage both money and tasks. It isn’t the particular tool or method you use that makes the difference. It is a shift in perspective and attitude. I’ve briefly summarized the YNAB approach below. After that, I’ll outline what I believe are the key shifts in mindset shared by personal finance and personal productivity.

YNAB Summary Here’s a quick summary of the overall method, as I understand it:

1. Rule 0: Identify your top priority for your money (growth, supporting your family, freedom, hobbies, fixing the house, security, retirement, learning)

2. Rule 1: Give every dollar a job, by creating accounts for each of the goals you want to fund (buying a house, saving for a wedding, buying a car, going on vacation), and assigning a portion of the money you currently have to each of them, until they are fully funded

3. Rule 2: Embrace your true expenses, by creating accounts for each infrequent, but predictable expense (car repair, doctor’s bills, new computer, Christmas gifts) and assigning a portion of the money you currently have to each of them, until they are fully funded

4. Rule 3: Roll with the punches, adapting to each month’s unique circumstances by pulling money from lower priority accounts to fund higher priority ones

5. Rule 4: Age your money, by waiting as long as possible from the moment money comes in, to the moment it is spent, which creates a cash buffer for riding out fluctuations in income and expenses

6. Engage

with your money consistently, by making intentional

decisions whenever money comes in about which accounts it should fund

7. Once all accounts have been funded, do whatever you want with your money!

Parallels to Productivity The parallels between managing a budget and managing time/tasks are striking. It makes sense that they would be: each one requires managing a flow of a valuable, but finite resource. They are both complex domains with many relevant factors to consider, that also have a tremendous impact on our quality of life and future. They both can be partially automated, but not completely, requiring us to make decisions to achieve the outcomes we want. Here are the principles underlying the budgeting method described in this book, that I believe apply equally well to managing our work:

1. Start by aligning with the deeper purpose Mecham recommends sitting down with your spouse or partner, and really taking the time to answer the question, “What do I want my money to do for me?” Everything else depends on the answer: if you value freedom and autonomy, your decisions will look very different from someone who values security and stability. It’s likewise very valuable to ask yourself, “What do I want my work to do for me?” Besides the obvious answer of “provide a paycheck,” the conclusion you come to has profound implications for where, when, and how you work. If you value creativity and self-expression, but an ever greater proportion of your to do list is filled with administrative tasks, you will eventually experience dissatisfaction and burnout, regardless of how many hours you work or how much it pays. And this isn’t a one-time effort: both your purpose and your work are constantly shifting, so revisiting and realigning them is probably the most important thing you can do for your long-term progress.

2. Replace black and white decisions with tradeoffs With both money and time, the less confident and sophisticated one’s thinking is, the greater the tendency to frame decisions as black and white, yes or no, good or bad. I think this is because the fear, uncertainty, and other emotions surrounding the topic make every decision feel dramatic and risky. The riskier a decision feels,

the less likely we are to take action until everything is just right (which often never happens). YNAB recommends replacing closed-ended, binary questions, such as “Am I within my budget this month?”, with open-ended ones, such as “Where can I pull funds from to balance my budgets this month?” This inquisitive attitude activates your curiosity, opening up new options you may not have previously considered. Likewise, a more sophisticated way of working replaces black and white questions, such as “Did I get enough done today?”, with more nuanced ones, like “What could I have done differently today?” This trains you in viewing your tasks not as good or bad, but as subtle tradeoffs between priorities that you can learn to navigate skillfully.

3. When stuck, surface information needed to make better decisions When we are stuck, whether in budgeting or productivity, it is most often because we simply don’t have the information required to make a confident decision. Instead of judging the feeling of stuckness or overwhelm as our fault, we can view it as a valuable indicator that more information is needed. In the YNAB approach to budgeting, not having any remaining funds in a “splurge” category doesn’t mean you’re being restricted or deprived. It means that you’ve chosen to use those funds to fund higher priority accounts. You and your true priorities are the source of your finances, instead of being victims of it. At work, we’re often seeking more “clarity” before moving forward on something. But there is always a clear next action available to you: any time you’re not sure how to proceed, surface more information. This can include reviewing your emails for the latest updates, talking to colleagues or your boss, or stepping back to make a plan. The trick is to perform these actions without getting sucked into them. You want to move quickly and touch lightly, staying at a high elevation and looking for only the information that will help you make better decisions about what to do next, postponing any heavy work until after you’ve made those decisions.

4. Tighten the feedback loop between your present and

future self Both money and productivity boil down to a relationship between your present and future self. It is the existence of a desired future that necessitates planning and decision making. We are extracting value from the current flow of money/time, to provide our future selves more freedom, wealth, or happiness. Whether you are sitting down to review your budgets, or review your priorities for the week, anything you can do to strengthen that relationship is valuable. Reflecting on the current month’s spending and whether it is in line with your budgets is really about fine-tuning your expectations and behavior. Doing so non-judgmentally allows your two selves to influence each other without fighting each other, encouraging them to follow through on each others’ promises.

5. Manage unexpected events by turning them into consistent routines Both money and time can be consumed by “unexpected” events. A death in the family requires a barrage of last-minute funeral expenses. A client threatening to walk away requires a flurry of unscheduled meetings and calls. But the truth is, the unpredictable is totally predictable. We know that life will throw these curveballs at us nearly every month, so it falls to us to prepare for the inevitable. YNAB recommends creating accounts for each of the “emergency” expenses we are likely to encounter at any point in the future, and to fund them up to a reasonable level. This ensures that when your dog needs a vet appointment, you have funds ready and waiting, instead of scrambling for cash. The same is true of managing a to do list. Many weeks it may seem unnecessary to perform a Weekly Review – emptying your email inbox, clearing your computer desktop, closing browser tabs, etc. But if we don’t do these things regularly, they tend to blow up right at the worst possible moments. Your computer runs out of space just as you need to download a large file. The new tab you open for an urgent task is exactly the one that crashes your browser. Preventative maintenance is what allows you to ride out the crises and emergencies, without being completely thrown off track from your priorities. It can mitigate the greatest risks with a minimal investment of time, freeing you to

take on more creative risks.

6. Create milestones to provide a sense of completion Managing flows of money or time is a never-ending process, which means there are few built-in stopping points. We can often feel starved for a sense of completion, for that celebration at the finish line. YNAB recommends funding an account only until it has enough funds, and then stopping. Instead of one giant “emergency savings” fund that is never quite big enough (and so tempting to “borrow from”), you have a series of smaller, more targeted savings accounts designated for specific purposes. Once all your accounts have been funded, you’re free to spend anything left over however you want! The same mechanism is valuable in productivity. Punctuating the never-ending flow of tasks with milestones – project completions, weekly reviews, and finishing the day’s to do list – are not nice-to-haves. They are absolutely necessary for providing closure and fulfillment. After reaching a milestone, you are free to spend your time and energy as you want.

7. Make plans, but adapt them to fit changing circumstances Implicit in the YNAB philosophy is the idea that there is no such thing as a failure, only a reprioritization. A budget for a specific category of spending is a plan, but like all useful plans, it is designed to change. If you go over your grocery budget for the month, that is neither good nor bad. It is a useful signal – your past self communicating to your present self that she has needs and priorities different from what you expected. What you do with that information is up to you. If it happens once or twice it can be treated as an anomaly to keep an eye on. If it happens month after month, it is probably a sign that you need to either change your expectations, or change your behavior. Likewise with a to do list, which is a plan for which actions you will take in the near future. We tend to either meticulously plan and prioritize our to do list, and then stick to it slavishly because of these sunk costs, or we spend no time on it, and feel like the whole week is spent reacting to emergencies. There is a middle ground: put real effort and intention into the to do list, and then adapt and

respond as the week unfolds.

8. Be honest with yourself and what is actually happening, instead of what “should be” There is a deeply seated human tendency, when things aren’t going how we believe they “should go,” to simply deny reality. We can make up justifications, rationalizations, and excuses effortlessly, and maintain them even when the impact on our health, happiness, and relationships becomes unbearable. Simply knowing what is happening is half the battle when it comes to money or productivity. Getting a hold on the “current state” requires letting go of the lenses and stories we use to buffer reality and protect our ego. This is why making a comprehensive Project List is so powerful – it lays out the current state of affairs in objective detail, allowing us to make fully informed decisions.

9. Create buffers or reserves between “incoming” and “outgoing” YNAB introduces the idea of “aging” your money, i.e. increasing the amount of time between the moment it comes in, and the moment it goes out. This creates a reserve of cash that you can draw on to even out fluctuations in income or expenses, or both. The idea is familiar in finance, but no less important in productivity. If tasks are arriving in front of you and immediately being executed, that looks like efficiency. But what are the chances that the thing landing in front of you is the most strategic or high-leverage thing you can do at this moment? Practically nil. This is where “capturing” open loops is so valuable. It’s not just that you’re freeing up mental capacity by writing things down. You are also creating a pool of diverse tasks that you can draw upon when you’re looking for a next action. The larger this pool, the better, because it provides you more potential options for what to work on, and more strategic combinations of tasks. This may seem counter-intuitive, because we’re taught that a small to do list is a good to do list. But as long as you can reframe each “task” from an absolute obligation, to a potential option, your freedom increases as your to do list grows.

10. Don’t try to fully automate – instead, make it quicker

and easier to make good decisions YNAB contrasts with the “set it and forget it” approach, arguing that you don’t actually want your money to be on autopilot. Instead, you want to make it easy to get the current financial picture, and to route funds to various accounts that have been set up in advance. Likewise with productivity, you wouldn’t want a “perfect system” to tell you exactly what to do each moment. There is at least as much creativity and intention required to decide what your work is, as doing it. As computers become smarter and smarter, this “meta-work” becomes more important, not less. Who will tell the computers the work that needs doing?

11. Don’t try to forecast the future, just make a plan for what’s current Mecham explains that what most people think of as budgeting is really forecasting – trying to predict how much money will come in, and how much money will go out, month by month and category by category. This not only is difficult and error-prone, it’s not really necessary for an individual’s finances. Their income and spending can change at a moment’s notice, so it’s more important to manage the money that’s currently in the accounts. Similarly with productivity, long-range plans aren’t really necessary for individual workers or even small businesses. There aren’t millions of dollars on the line, or dozens of collaborators to synchronize, so the horizon of planning shifts to the present and very near future. Document what’s on your plate now, make a plan looking a few days into the future, and that will be enough most of the time.

12. Scarcity can help us be more concrete about our priorities Scarcity in either money or time is one of the constant scourges of modern life. But it can actually be a tremendous source of clarity. When funds dry up, that is the exact moment when you need to decide what’s most important, and what can go. Talking to a financial planner recently, he said the biggest mistake people make is waiting until they’ve “put their ducks in a row” to talk to a planner. The best time to talk to one is when you’re deepest in debt, with no income, because that is when a plan can make a difference.

The same is true of work – an abundance of time often leads to wasted effort, lack of direction, aimlessness, and unclear priorities. Having a full-time job or a family to take care of can be a beautiful constraint (members-only link), forcing you to approach your goals from an unorthodox angle.

13. Let go of perfectionism, unrealistic goals, and selfpunishment as the greatest enemies of progress The greatest enemy of effective self-management is when we start viewing that self as an enemy. It’s so easy to start internalizing disappointments and frustrations, making them mean something about our character. Letting go of self-judgment feels scary, because it seems like the only tool we have to whip our selves into submission. But self-punishment can only take you so far. It can help with the small things, but when it comes time to step into your greatness, to fulfill your potential, you simply cannot be at war with yourself. This is the connection between healing and performance: every harsh voice in our head is an echo of a wound or a trauma from our past. Turning them into voices of support is the journey of personal growth. It involves forgiveness, of yourself and others. It can include accessing and releasing things in the body. It often needs to be done with others, seeing and being seen, reinterpreting your view of your own identity through the eyes of others.

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The 5 Challenges of Becoming a Digital Nomad As we’ve moved abroad to Mexico City, these have emerged as the top five challenges in making the transition to remote work.

1. Location-independent income This is, of course, the big one. No matter how cheap a foreign country is, you still need to live on something. Not to mention save and invest for the future. This has fortunately become possible for me over the last couple years as Forte Labs has transitioned from offering primarily live trainings, to primarily online courses and other information products. The team is already mostly remote, so that won’t be a problem. I will still need to do some travel for conferences and consulting work, but I do that already anyway. I wish I could say this was a long-term strategic plan, but it wasn’t. I made the transition because online products better fit my interests, needs, and skills, and only more recently did I realize they also made my location irrelevant. On Lauren’s side, she is leaving her current job in San Francisco and taking some time off to decide what she wants to do next. The significant drop in living expenses should give us some extra buffer to allow her to do that. I think having a location-independent source of income is the biggest barrier to most people living abroad. There have been several waves of digital nomads entering the exo-workforce, defined mainly by their profession and the connectivity they require to stay productive:

1. Pre-digital: artists, writers, journalists, photographers, and others who didn’t need connectivity for long periods

2. 1st wave: solo entrepreneurs and internet marketers living in tropical locales, who only needed occasional connectivity

3. 2nd wave: software developers and other information-intensive jobs, who need consistent connectivity but can work independently for substantial periods

4. 3rd wave: other knowledge workers who primarily work on a computer, who need constant connectivity and collaborate frequently

We’re currently in the third wave, which is why it’s the least clear. Will this be the great explosion of remote work long predicted? Or just another small group joining the movement? What seems to be most unique about the current wave is that there are entire remote-first organizations, and that they see it not just as a cost-cutting measure, but as a strategic advantage. Influential companies like Github, Automattic, and Zapier are aggressively and vocally remote, seeing it as a way to attract and retain talent with strong salaries in affordable locales. Although the range of jobs that can be done remotely has expanded a lot in recent years, it remains a fairly limited slice of the workforce. This Gallup survey shows 43% of employees working remotely at least part of the time, but only 31% between 80-100% of the time. And it remains much harder for certain industries like retail, healthcare, manufacturing, and education.

2. What to do with our belongings This has been a surprisingly hard one. I would love to just give it all away, but that’s not very responsible. What seems to be emerging is a rule of thirds:

1. Sell about ⅓: the high-value but not personally important items that are worth the trouble of selling

2. Give away about ⅓: the things that our friends or family happen to need or want, with the rest going to charity as a donation

3. Save about ⅓: I’d prefer this was much less, but with the possibility that we’ll only be gone a year, a lot of things will still be just as useful and are worth keeping. Also, things with sentimental value. The key unknown variable seems to be how long we’ll be gone. Our current commitment is at least a year, but if that was much longer it would have quite an impact on these decisions. It’s not much of a risk though since we have space in our parents’ houses, and don’t need to pay for monthly storage. One last note: the hardest part about this one is selling things. There are good ways to sell individual items (Craigslist, OfferUp, Letgo), but selling such a variety of things seems to require a lot of time taking photos, writing descriptions, messaging back and forth, agreeing on a price, scheduling pickups, etc. We need digital garage sales for people without garages! At the same time, getting rid of stuff is one of the things I’m most excited about. I’ve been very inspired by Marie Kondo and her “tidying up” method, and the message of The Minimalists. Over 6 years in the San Francisco Bay Area, we’ve accumulated an extraordinary amount of crap. I’m looking forward to downsizing.

3. Establishing a social life Talking to many remote workers and digital nomads in recent months, both short term and long term, a common thread has emerged: as exhilarating as living abroad can be, it is lonely. Taking a quick tour of Southeast Asia or South America is one thing. You may be traveling with friends, or meet people in the many hostels specifically designed for this purpose. But once you drop out of the tourist crowd and settle in somewhere, the lack of built-in community quickly becomes apparent. On the other hand, I think I’ve experienced more loneliness living in the U.S. than abroad. So I don’t think it’s a matter of location, but of mindset and social habits. I’ve always addressed this the same three-fold way, during each of my abroad experiences in Brazil, Colombia, and Ukraine:

1. Stay in one place for a long stretch: by putting down roots, you really can grow a community from scratch. Your foreignness and lack of existing relationships can actually make this much easier. You automatically stand out, and people will notice you’re a clueless foreigner with no street smarts, and take you in.

2. Commit to the culture and language: it’s possible to be physically located abroad, but spend most of your energy on existing habits and relationships. There is an important mental shift that happens when you decide that you are going to become part of the culture. Listen to their music, watch their TV shows, change your computer to the local language, eat their food. Commit to learning the language as soon as you arrive, even if you don’t think you can master it. The experience will be totally different.

3. Get involved with local groups and activities: these were built in

for my previous abroad experiences. In Brazil I worked for a local non-profit school, which embedded me deeply in the community. In Colombia I went to work every day at a microfinance bank. And in Ukraine I was a Peace Corps volunteer, which came with a whole set of responsibilities and relationships. We’re going to need to work a little harder in Mexico City for this last one. Spending most of our time together and working mostly on our computers, it would be very easy to just be “Americans while abroad.” Here are the actions we’re taking to ensure we embed ourselves in a community: Staying initially in private room Airbnbs with local residents, so we can hang out and talk to them Choosing a place to live in a central, walkable neighborhood Asking our friends/contacts for introductions to interesting people in the city, who we’ll invite to meet up for coffee Taking other classes and joining other groups related to our interests (like salsa dancing, cooking classes, workout classes, etc.) Joining a coworking space within walking distance of where we live, so we’re not cooped up at home

4. Maintaining existing relationships As important as it is to form new friendships, we also don’t want to lose existing ones! This is another common challenge I’ve heard from long-term expats. This is partly why we chose Mexico City as our home base. It isn’t very far from California, and flights are cheap. With scheduling flexibility, we can get roundtrip flights on Volaris for as cheap as $180, which means we’ll probably come home every couple months. It’s also a city many people want to visit, and we’re planning on having an extra bedroom to make visiting us as enticing as possible. I’m currently researching various travel hacking techniques, including what’s known as “miles churning” – taking advantage of signup bonuses and other promotions to rack up free airline miles. It’s quite a rabbit hole that you could spend all your time diving into, but I think there is a minimal yet strategic approach that captures most of the benefits with little time required.

5. Mindset shift I think for most people, the most fundamental challenge is the shift in mindset required. Especially if you didn’t grow up traveling or haven’t spent much time overseas, it can seem like a scary place. Much of the news we hear is of danger and disaster, which just doesn’t reflect the day to day reality. The places I have lived were considered either outright warzones, or at least unstable. But my memories are filled with the warmest memories of close-knit communities that embraced me without a second thought. My recollection is of fascinating cultures, teaching me things I never knew I wanted to learn, pushing me far beyond my comfort zone but with love and caring. The mindset we want to shift to is one of curiosity, adventure, and wonder. To be unattached to what happens and when. To say yes when we don’t even know what we’re saying yes to. I’ve found time and again that trusting people I hardly know, putting my faith in those who seem so different from me on the outside, renews my basic faith in humanity. I don’t know of any other experience that makes me feel so alive, and I can’t wait to begin the next leg of the journey.

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Emergent Strategy: Organizing for Social Justice When I moved from San Francisco to Oakland in 2014, I was just trying to pay cheaper rent. I never expected to be influenced by the movements that flow through Oakland’s veins: the movements for social justice, for environmental justice, and for black liberation. I’ve since had the privilege of working with some of the most extraordinary black leaders, organizers, and activists in the San Francisco Bay Area. Through the courses I’ve taken at Landmark, through local groups and events such as the East Bay Meditation Center, and through exposure to the network my partner Lauren has developed through UC Berkeley and the Greenlining Institute. I’ve stayed only on the furthest outskirts of this incredible community, but even that light exposure has profoundly changed how I think about my work. It was through Lauren that I first heard of a book called Emergent Strategy (Affiliate Link), by adrienne maree brown. The title immediately caught my eye, echoing my interest in Emergent Productivity from several years before. I began to hear about it through different channels, from different people, and could see this book was catching fire in the movement-building world. I decided to read it, and found a new world of ideas and stories that were somehow both completely novel, and deeply familiar. I found a new language to talk about healing, growth, liberation, forgiveness, and change. I found a body of work bridging and connecting a stunning diversity of sources and fields, much like I try to do myself. But with a far stronger connection to what is happening on the ground, in the lives of people who don’t have access to the same resources and opportunities. This is my summary and interpretation of the book, in the hope that it will reach more people who might not otherwise pick it up. I’m going to paraphrase in my own words, and incorporate some of my own experiences and learnings from the world of productivity and effectiveness. Assume all substantive ideas come from the book.

Emergent Strategy: Shaping Worlds, Shaping Change Adrienne maree brown is an author, activist, social justice facilitator, healer, and doula living in Detroit. She has been a part of many of the most significant social movements in recent years, including Black Lives Matter and Occupy Wall Street. Her book is a summary and exploration of what she’s learned from her experiences as an organizational leader and facilitator. It’s not written at all like a typical non-fiction book. Paragraphs of meandering text are interwoven with poems, song lyrics, quotes, lists, and diagrams. She moves freely from the most concrete advice to the most philosophical ideas. Her influences include famous activist leaders like Grace Lee Boggs, but also the science fiction author Octavia Butler, ideas from biomimicry and permaculture, and popular culture and music.

Emergence and biomimicry It all begins with the idea of emergence. In brown’s eyes, emergence is not an abstract concept from information science. She draws instead from nature – her examples include roaches, ants, deer, fungi, bacteria, viruses, bamboo, eucalyptus, squirrels, vultures, mice, mosquitos, and dandelions. She studies how mycelium grow underground in thread-like formations, gaining strength by connecting their roots to one another. She admires how ants and starlings are able to coordinate in large numbers and react to their environment by following simple, local rules. Ferns and their fractal patterns are the inspiration to look for small-scale solutions that propagate outward and impact the whole environment. Dandelions are admired for their extreme resilience, that they can thrive and spread despite being uprooted and trampled on. Humans have traditionally identified most with the “kings” of the jungle, like lions. We aspire to be powerful as individuals, claiming a territory and defending our reputation. But brown notes that despite their isolated ferocity and alpha power, it is these very animals that are going extinct as our climate changes. The resilience of more decentralized, interdependent life forms comes from their ability to adapt and collaborate, while maintaining core practices essential to their survival. This model of emergence is practical instead of theoretical. It emphasizes “critical connections over critical mass” – it is the depth of relationships that determine the strength of a system. Brown’s definition of emergence comes from

Nick Obolensky: “Emergence is the way complex systems and patterns arise out of a multiplicity of relatively simple interactions.” It is these “simple interactions” – from how we relate to the thoughts in our own heads, to how we show up in our relationships, to how we exist as local communities – that create the patterns that give rise to our ecosystems and societies. From this perspective, deep systems change starts with shaping the smallest patterns of our daily lives. We can, in brown’s words, “…intentionally change how we live in ways that grow our capacity to embody the just and liberated worlds we long for.” This is very much in line with my work, examining how the smallest and simplest of daily work practices, upon closer examination, unfold into fractal worlds of amazing complexity and depth. It is much faster and more effective to look for insights inside these worlds, then to go searching for an answer outside ourselves somewhere. Brown is also, whether she knows it or not, a fan of compression. Here are her core principles of emergent strategy:

1. Small is good, small is all (The large is a reflection of the small) 2. Change is constant (Be like water) 3. There is always enough time for the right work. There

is a

conversation in the room that only these people at this moment can have. Find it.

4. Never a failure, always a lesson 5. Trust the People (If you trust the people, they become trustworthy) 6. Move at the speed of trust 7. Focus on critical connections more than critical mass—build the resilience by building the relationships

8. Less prep, more presence 9. What you pay attention to grows

These principles resonate deeply with what I’ve discovered in the world of personal effectiveness. Here is how I translate them: Small is good, small is all (The large is a reflection of the small) To find deep insights, look closely into the inner workings of how you manage your daily work, from how you manage email and your calendar, to how you decide what to work on next. Change is constant (Be like water) Invest in your capacity to adapt, expecting your work and your life to change, instead of trying to prevent them from changing. There is always enough time for the right work. There is a conversation in the room that only these people at this moment can have. Find it. Choosing what the work actually is, and with whom you will do it, has far greater leverage than how you perform it. Never a failure, always a lesson Every experience you have is fuel for creative inspiration. The bigger the failure, the better the fuel. Trust the People (If you trust the people, they become trustworthy) Learning how to trust people, and how to allow them to trust you, is a far greater source of leverage than all the productivity tips, tricks, and hacks ever conceived. Move at the speed of trust How fast you can move is determined by how much trust you have. And people won’t trust you unless you are vulnerable with them. Focus on critical connections more than critical mass—build the resilience by building the relationships A relationship to the right person can have more leverage than a large group agreeing. Invest in that relationship because it is critical.

Less prep, more presence Preparation has diminishing returns after a while, while presence has exponential returns. The sooner you move from preparing to being present, the better your results will be. What you pay attention to grows Attention is the rarest and most precious resource we have. It can be shaped and cultivated by investing attention in the first place, in an endless cycle.

Science fiction as visionary fiction From studying the deep past of the biological world, Brown shifts our attention to envisioning the future. Specifically, she dives into science fiction as a tool to help us see worlds that do not yet exist. One of the biggest influences on her work has been Octavia Butler, a black woman who wrote science fiction far ahead of her time. She argues that: “We are in an imagination battle. Trayvon Martin and Mike Brown and Renisha McBride and so many others are dead because, in some white imagination, they were dangerous. And that imagination is so respected that those who kill, based on an imagined, racialized fear of Black people, are rarely held accountable. Imagination has people thinking they can go from being poor to a millionaire as part of a shared American dream. Imagination turns Brown bombers into terrorists and white bombers into mentally ill victims. Imagination gives us borders, gives us superiority, gives us race as an indicator of capability. I often feel I am trapped inside someone else’s imagination, and I must engage my own imagination in order to break free.” Brown embraces the tools of sci-fi to help paint a different picture of how the future could be. It’s not enough to make those futures plausible or realistic. Visions of dystopia are nothing if not plausible and realistic. We must also make just and liberated futures irresistible. I absolutely love this, as it aligns with all the research on behavior change. We don’t change our behavior out of shame, or punishment, or pressure, or even desire. We change out of pleasure and freedom and love. This is why Brown calls herself a “pleasure activist,” and I’m going to as well. What’s so important to understand is that we aren’t trying to create a monolithic, homogeneous future. Brown notes that many sci-fi stories describe an antiseptic and boring future full of stark modern architecture and invasive technology. It’s a future that few people would actually want to be a part of. Instead we need to equip everyone with imagination tools, so that they can create an abundance of futures, where everyone doesn’t have to be the same kind of person. As the Zapatistas say, “The world we want is one where many worlds fit.” The only way to break out of someone else’s imagination is to imagine ourselves into a new one.

Dialectical humanism and healing As brilliant as these intellectual explorations are, where this book really shines is its exploration of the human heart. Brown returns to the idea of “dialectical humanism” that she learned from her mentor Grace Lee Boggs: that there is a cycle of collective transformation of beliefs that occurs as we gather new information and experiences, meaning that, over time, we can understand and hold a position we previously believed to be wrong. This idea strikes to the heart of the modern age, where we each seem to be descending deeper and deeper into our private filter bubbles. The ability to change one’s mind seems to be the key capability we are losing as a society. Maybe we never had it. Boggs is quoted arguing that “…whenever a person or an organization or a country is in crisis, it is necessary to look at your own concepts and be critical of them because they may have turned into traps.” We are presented with fewer and fewer opportunities to do so in a world where we can increasingly hear only what we want to hear. This is the point where an understanding of emergence is so critical. Often this topic leads to grand discussions of the state of our democracy, the role of social media and partisan politics, and blaming specific individuals or groups. I’ve always felt that this is an unproductive level to focus on, at least for me and my work, and brown gives me the words to understand why: the trends we are seeing in the world are the result of simple, local interactions. They arise inexorably from who we are being in our private thoughts, in our relationships, and in our communities. This has helped me understand the role of healing, which I’ve always been uncomfortable with. My story has been that I never had any real trauma growing up, at least compared to most people I know. Why should I have anything to heal? I saw healing as a process of remediation, of getting “back to normal.” And didn’t feel I deserved the indulgence. Even as I’ve had experience after experience that can only be described as healing, I’ve resisted the idea that everyone can or should pursue it. But brown offers a series of reframings for what healing actually is that I find tremendously empowering. First, healing is not “fixing oneself.” It is the re-opening up of the parts of ourselves that have closed. They closed for good reasons, to help us survive. We

honor those experiences and those decisions, while gently inviting those parts to open up once again. Like a child who used to throw tantrums to get their way, but now has the words to say what they need. It can take us a while to exercise this newfound ability. Second, healing is painful, but not as painful as continuing to ignore it. I think often we fear that the healing process will be as painful or more painful than the thing that originally hurt us. But healing is, in fact, always occurring. It is a natural phenomenon of the human heart, and therefore we need only embrace it and let it proceed. Paul Ferrini says that: “Your life is your spiritual path. Don’t be quick to abandon it for bigger and better experiences. You are getting exactly the experiences you need to grow. If your growth seems to be slow or uneventful for you, it is because you have not fully embraced the situations and relationships at hand. To know the self is to allow everything, to embrace the totality of who we are—all that we think and feel, all that we fear, all that we love.” Lisa Thomas Adeyemo says that “Everything, given time and nurturing, is moving toward balance and healing. The mushrooms that cleaned the land after nuclear trauma…the process of forest growth after a fire…the way our skin heals after a cut…stronger than before. Healing is organic, healing is our birthright.” Third, that healing opens up tremendous capacity to think, to feel, and to know. It unlocks vast new channels for creating the life we want to live, and for impacting others. This is why social impact and personal growth are so intertwined. You cannot create change that you yourself have not experienced. You cannot create freedom for others via your own suffering. You are a seed, and that’s not how seeds work. When you open yourself up to the lessons that life is trying to teach you, new things start to flow: truth, comfort, ease, joy, wholeness, acceptance. These things are not achievements far out on an endless horizon. They are waiting at the intake valve, ready to arrive the moment you allow it. And fourth, that healing is not a linear, one-way process. It’s not that everything gets better and easier and happier all the time. Healing is not synonymous with self-improvement. Brown asks us to consider a bold series of propositions: That the broken heart can cover more territory

That perhaps love can only be as large as grief demands That grief is the growing up of the heart that bursts boundaries like an old skin or a finished life That grief is gratitude That water seeks scale, that even your tears seek the recognition of community That the heart is a front line and the fight is to feel in a world of distraction That death might be the only freedom That your grief is a worthwhile use of your time That your body will feel only as much as it is able to That the ones you grieve may be grieving you That the sacred comes from the limitations That you are excellent at loving In other words, taking on the work of healing involves more heartbreak, and more grief. Feeling more involves feeling more in all dimensions, including the ones you’re not currently comfortable with. It involves losing control of what you allow yourself to feel. This is why it’s scary sometimes. Returning to her work in movement-building, brown says that change doesn’t come simply from thinking differently. This is the deep misconception at the heart of self-improvement. That you can just think different thoughts, thoughts you read in a best-selling book or online course, and that everything else will unfold automatically from there. It isn’t true. The factual learning is necessary, but only as a staging ground. Change actually occurs through direct experience, doing exactly the thing you are scared to do, which allows you to shift what you are capable of understanding, what you are capable of feeling, and what you are capable of

practicing. Change emerges from the correlation between feeling more, and having more choices.

Building movements The book rather unexpectedly becomes a how-to on “How to Build a Movement.” Brown has an unapologetic practical bent, which I appreciate. She starts with what the current paradigm teaches, in our homes, in our schools, in our organizations, and in society: That we should deny our longings and skills, in favor of work that fills hours without inspiring our greatness That tests and deadlines are the reasons to take action, which favors people with good short-term memories and who respond well to pressure, who become leaders who depend on urgency-based thinking even when it’s not required That we need to compete with each other in a scarcity-based economy that destroys the abundant world we actually live in That the most valuable skills involve being able to manipulate and sell to each other, instead of learning and collaborating That the natural world is to be manicured, controlled, or pillaged to support our consumerist lives (including the natural lives of our own bodies) That factors beyond our control – our skin color, gender, sexuality, ability, nation, or belief system – determine our path and quality of life That we are valued only to the extent we can produce – only then do we deserve food, home, health care, and education That our success is measured in financial results, regardless of its impact on others and the environment

That we should swallow our tears and any other inconvenient emotions That we should just be really good at what’s already possible, and to leave the impossible alone But Brown’s criticism is not reserved for “the powers that be.” She turns next to social impact organizations, who so often replicate the very same power structures they claim they are trying to dismantle. They often have singular, charismatic leaders, top-down hierarchies, money-driven programming, destructive methods of engaging conflict, unsustainable work schedules, and a lack of accountability to prove they are having the impact they claim. This is why nonprofits can have the most challenging and unbalanced work cultures, characterized by burnout, overwork, underpay, unrealistic expectations, personal drama, movement splitting, mission drift, and the inability to make decisions. I’ve experienced these patterns firsthand. Most of my 20s were spent trying to “do good.” Teaching English in the favelas of Rio de Janeiro, working in microfinance in Colombia, teaching leadership and community service in the Peace Corps. I ultimately left because, more often than not, these organizations had the best of intentions but lacked effectiveness. They simply couldn’t accomplish what they set out to accomplish, and the aura of social impact shielded them from any scrutiny that might have changed things. I moved to business, where results were measured and companies were at least sensitive to one source of feedback – their customers. I so admire brown’s insistence on taking personal responsibility for how these events play out. She tells story after story of her raging individualism, her challenges in staying connected to her body and spirit, and resistance to leaning on others. Like me, she is naturally brainy and self-reliant, yet has come to realize that these wonderful qualities are simply not going to be the important ones moving forward. She says (emphasis mine): “I am socialized to seek achievement alone, to try to have the best idea and forward it through the masses. But that leads to loneliness and, I suspect, extinction. If we are all trying to win, no one really ever wins.”

And continues: “I have to use my life to leverage a shift in the system by how I am, as much as with the things I do. This means actually being in my life, and it means bringing my values into my daily decision making. Each day should be lived on purpose. This has meant increasing my intentionality about being with others. Adapting to the changes of life, yes, but with a clear and transparent intention to keep deepening with my loved ones and transforming together…I am living a life I don’t regret. A life that will resonate with my ancestors, and with as many generations forward as I can imagine.” The banner she flies is a quote from Albert Camus, given special meaning as a black woman: “The only way to deal with an unfree world is to become so absolutely free that your very existence is an act of rebellion.”

What building a movement requires So what does it take to successfully build a movement, with ourselves as the starting point?

Being seen It is all too easy to project our desire for change onto the outside world. To seek to fix others as a way of avoiding fixing ourselves. It was this impulse that drove me for years. Which is why the first step is allowing yourself to be seen. And to be known. It is being seen and accepted as whole beings that begins the healing process. It begins to release our resistance to loving ourselves exactly as we are, right now. Which allows us to love those around us, just as they are. Instead of making our love contingent on something, or withdrawing it as a threat. The modern world gives us so many ways of not being seen, including allowing only parts of ourselves to be seen. It takes great courage to put down the social media handles, to allow the flattering frames to fall away, to show up and to be vulnerable when we feel most at risk. There are always moments of trauma and loss of control where we have no choice but to be seen. But we have the choice to make it a way of living, to do it on purpose. When you allow yourself to truly be seen, an amazing thing happens: you realize that your very existence, who you are, is in itself a contribution to those around you. Not what you do or what you produce, but just your presence. Have you ever heard a more radical idea? We are taught that love is about belonging exclusively to one person or community. That therefore we must contort ourselves in order to ensure continued belonging. We are taught that our value comes from what we produce, and that certain emotions impede production. Vulnerability is the fundamental reversal of this logic. Brenda Salgado writes: “Nature has taught me so much about moving with the seasons, that we need to honor times of harvest and times of rest. That the frenetic pace of doing, doing, doing, without being present with each other and the season we are in, what is happening around us, is unnatural and counter to life. So it has made me realize how important community ceremony and celebration is to our efforts to transform the world.”

Being wrong A friend of mine has a Post-it note in the corner of his laptop that says: “Be wrong more.” I love that. As a thinker, I am addicted to being right. Like any addict, I will burn relationships to the ground if I can have just a little bit of “being right.” I’ll leave communities, betray my values, and justify it all with my self-righteousness, as if my very survival depended on it. Brown describes her experiences with leadership, how the ability to be wrong and then to quickly pivot her position is key to her ability to lead. I’ve found much the same thing. That the longer I wait before releasing my viewpoint, the more painful and heavy the experience of life becomes. Often this begins with just naming something, pointing out a pattern that is present in my family or my business before I know the solution or even the cause. This feels risky, because more often than not the cause is me, and the solution is not-me. Brown notes that the capacity to be wrong allows you to be in relationship in real time, instead of defending the past. She asks us to consider that “…the place where you are wrong might be the most fertile ground for connecting with and receiving others.” If you are not able to be wrong, you can’t access this most fertile ground.

Art Art is also a critical component of building a movement. Brown notes that “Art is not neutral. It either upholds or disrupts the status quo, advancing or regressing justice.” She recounts the teachings of her meditation teacher, Black Zen teacher angel Kyodo williams: that our access to the global scale of suffering has become immediate, through technology, but we have not developed the capacity to be with that increased awareness of suffering. In her meditation retreats, williams teaches people how to choose where their attention goes. When overcome with grief, sadness, loss, desire, anger, or restlessness, to really be with those emotions, and to sense what is needed. This is where our work crosses paths most clearly. I find it very curious that the word “organizing” is used primarily in two contexts: organizing physical spaces or computer files, and organizing people in social movements. Maybe this isn’t a coincidence. What they have in common is that they involve “Organizing and fortifying ourselves so that we can source from our longings, health, love,

dreams, and visions, from our strength and our connections with each other.” Being organized, in both senses, involves arranging your environment so that you have ready access to the greatest resources at your disposal. It involves clearing away what is obscuring your vision and your movement, making hard decisions about what matters and what doesn’t, distinguishing between what you can control and what you can’t, and acting with more elegance and power. The heart of efficiency is that there is nothing dragging or diverting the energy of the work. From digital files to physical spaces to people, there are ways of making it vastly easier and more enjoyable to move in the direction we want. And what is easy and enjoyable is sustainable.

Cultivating small practices The ground level of emergent strategy is made up of small practices we integrate into our daily lives, which draw the patterns that metastasize into the structure of society. Brown lists the practices that she has integrated along her own path: “meditation, somatics, visionary fiction, facilitation, working out, yoga, intimate community on social media, check ins with woes (those who are also Working on Excellence) and buddies, orgasmic meditation, sex, self-documentation (selflove selfies! Learning to see beauty and power in my standard breaking appearance), sugar shifting, sabbatical (big one in 2012, annual mini-sabbaticals since then), poetry, unscheduled time, moon-cycle rituals, tarot (I am such a fan of this practice that I have bought five other people tarot decks), sage and frankincense cleansing of my home, journaling.” The key words, I think, are “integration” and “practice.” You can attend a weekend training or retreat that introduces you to a new practice. But it is the regular routine that gives it power. Notice that tightening feeling in your chest? Being willing to try on new practices in such a fluid and unattached way requires releasing the high stakes game of success vs. failure we often adopt when it comes to “habit formation.” Maybe you’ll stick with the new practice, and maybe you won’t. Over the years I’ve discarded far more than I’ve adopted. And many are appropriate only for a season of life, and after that can fall away.

Deep, slow, intentional work I found this fascinating: that brown traces many of our current challenges back to “urgency-based thinking.” This involves approaching everything as an urgent

problem requiring extraordinary measures, and seeking quick fixes instead of addressing the root of the problem. Changing the economic or political system won’t magically fix the situation. So often these systems are alternatives in name only, and amount to changing the window dressing. More fundamental is the aura of scarcity that pervades so much of our thinking: not good enough, not fast enough, not big enough. What they have in common is “not enough.” The real alternative is to take on the deep, slow, intentional work of personal growth. This work is messy as hell: letting go of our stories, taking responsibility for our lives, giving up our pride and ego and self-righteousness. This work isn’t glamorous, doesn’t give you status points, and never ends. But it opens up tremendous new capabilities for speaking, listening, and being with each other. As we expand our capacity to feel our bodies, we become more honest, because the body never lies. As we heal our wounds, certain forms of hierarchy naturally fall away, as people realize they don’t have to consent to it. Other forms of status remain as people realize it is not a threat. Brown says, “When we can stand in knowing another person’s power without feeling threatened, that can be powerful in itself…Being able to really see another person’s expertise without being upset by it.”

In parting It is comforting for me to realize that the societal transformation described above is inexorable. Yes, it depends on us. But it also doesn’t. I always remind myself, when things get too weighty and dramatic, that it’s all just the laws of thermodynamics at work. We are the ones who add the meaning and the emotion. This movement of movements can be seen as just the next stage of our evolution. Richard Strozzi-Heckler writes, “The evolutionary thrust surges through us as dreams, sensations, longings, images, and inexplicable utterances and gestures. We are constantly adapting, creating, filling, emptying as we become the dream.” Removing the sense of personal risk opens up this moment in history as an opportunity. Something is going to happen, and our choice is in what part to play. We can be the friction, or we can be the flow. We can withhold our ideas and our energy, or we can share them. The amazing thing is that there is room for every single person’s contribution. When we share our ideas, they become more complex, more interesting, and more likely to work for more people. When we share our ideas, they become bigger than ourselves, which means they also become bigger than our fears, our doubts, and our insecurities. Loretta Ross teaches us that, “When people think the same idea and move in the same direction, that’s a cult. When people think many different ideas and move in one direction, that’s a movement.” Brown’s question for us is, “What are you embodying in your work and in your life?” Given that you are a seed of the future, what are you a seed of?

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The Essential Requirements for Choosing a Notes App as Your Second Brain I believe there are ten core capabilities that software uniquely provides to the note-taking process:

1. Searchability: type in a few characters and see everything that matches, regardless of where it’s located

2. Duplication: duplicate your files, either to back them up, or create a new version while retaining the original

3. Access anywhere: keep files synchronized across devices, so you can access your files anywhere

4. Shareability: share a file with a friend or collaborator without losing your own copy

5. Editable: edit or change the content of your files, including the text, the formatting, the structure, and other elements

6. Upgradability: add or enhance functionality to your notes over time, as new features come out

7. Transferable: content can be moved from one place to another, through copy-and-paste for example

8. Linking: you can add clickable links, either to other files, or to external websites

9. Multimedia: save a wide variety of kinds of media, including text,

images, videos, links, PDFs, and others

10. Meta-data: many pieces of data about your notes, such as location, date, device, and size, can be recorded automatically by software

11. Automation: certain kinds of content can be captured automatically, such as social media posts, emails, and web bookmarks But it can be difficult to know exactly what the essential features look like. This article will describe what I believe to be the essential features for any app to serve effectively as your Second Brain, according to the methods I teach in my online course Building a Second Brain. Deal breakers 1. 2. 3. 4. 5. 6.

Quick capture and editing Scales to thousands of notes without performance lag Basic formatting options Strong search feature Ability to handle images and attachments Private space, with public sharing

Must-haves 1. 2. 3. 4. 5.

At least 3 levels of hierarchy Many ways to capture information Native and web versions Capturing and syncing across multiple devices Exportable as plain text

Nice-to-haves 1. 2. 3. 4.

Side-by-side viewing Bullets or lists Automatic date stamps Tags

Deal breakers 1. Quick capture and editing My most fundamental test of a knowledge capture app is whether, if you’re walking down the street and a brilliant (or wacky) idea suddenly pops into your mind, you will actually pull out your phone and capture it. This is a common daily occurrence for photos, but not so much for ideas and insights. I can’t imagine this happening with Google Docs, or other heavy-duty text editing apps. One of the key strengths of notes apps is that they are made for just this kind of quick capture. The same is true for editing – you need to be able to quickly find a note you’ve already saved, and opportunistically add, remove, or edit it, on a mobile device if necessary. 2. Scales to thousands of notes without performance lag One of the critical principles for building a Second Brain is that each note should contain information from only one source. Instead of giant Microsoft Word or Google Docs files, each note should be small and agile, so it can easily be mixed and matched with other notes. This principle inevitably leads to creating thousands of notes in a relatively short amount of time. It’s very important that the collection can grow quickly, without performance lags. 3. Basic formatting options Basic formatting options (such as bold, italics, underline, font colors, and highlighting) are an essential feature for quickly annotating text in a notes app. They are both very familiar for anyone who has done word processing, and customizable for those of us using specialized methods (such as my progressive summarization technique). It doesn’t matter exactly which formatting options are available, but I recommend at least 3 distinct options that can be overlaid on top of each other (as in, a given passage can have at least three formatting styles applied). I use bold, highlighting, and underlining, but any of these can easily be substituted for another style. What matters is that you use them consistently.

4. Strong search feature With thousands of notes spanning hundreds of projects and topics, search is an essential feature of a notes app. Even with the powerful organizational methods I teach, it is often the very best way to go straight to the note you’re looking for. It is essential that the search feature searches both the body of the note, as well as its title and meta-data. Ideally, the search feature also includes auto-complete (making suggestions as you type). 5. Ability to handle images and attachments Although text tends to be the most common format for ideas, learnings, and observations, images are becoming a more and more important part of our creative vocabulary. Your notes should be able to include images within the body of the note, not as an attachment that you have to click to view. This ensures that you will regularly come across them, serendipitously making new associations and connections. Other kinds of files, such as videos, GIFs, PDFs, sound files, webpages, and others, should also be included, as attachments if necessary. 6. Private space, with public sharing It’s important that your notes app serve as a private space for the ideas that you’re not ready to share with the world. You should be able to jot down the most random thoughts, write out long personal reflections, sketch crazy harebrained schemes, all without the fear of criticism. At the same time, it’s just as important that you have a way to share those ideas as soon as they’re ready for showtime. You can always copy and paste something to social media, of course, but ideally you’ll have a share feature integrated directly into the app you use. The less friction there is in sharing, the more often you’ll do it.

Must-haves 7. At least 3 levels of hierarchy Although this is a strict requirement for my PARA organizational system, I believe that in general at least 3 levels of hierarchy are needed for anyone to properly organize a large number of notes. In Evernote, the 3 levels are individual notes, which are contained in notebooks, which are contained in stacks. Other notes apps may use folders instead of notebooks, but the important thing is that you can put a group of related notes in one place, and they’ll stay there. Numerous studies have shown that, despite the prevalence and effectiveness of search, people still overwhelmingly prefer to navigate through discrete containers to find their files. I believe this satisfies our sense of spatial awareness, and also provides many opportunities for serendipity (like wandering through the stacks of a library). 8. Many ways to capture information Because we are using a notes app as a “universal inbox,” it is important that there are many different ways to get data into it. Evernote, for example, has numerous options for importing content: Web clipper (for capturing web pages) Menu bar helper (for access through the computer menu bar) Email capture (a customized email address you can forward emails to to be captured) Mobile apps on popular platforms Dropping files on dock icon (Mac only) Copy and paste Click and drag into a note Third-party integrations (such as Bookcision for Kindle highlights,

and IFTTT and Zapier for almost anything else) Think about the 2 or 3 most common kinds of information you tend to save, and make sure you have a frictionless way to do so with the notes app you use. 9. Native and web versions Many apps have gone web-first, meaning that they expect you to access them primarily through a web interface. This approach has many benefits, but it doesn’t work for notes apps. Your greatest enemy is friction, and the wait times for loading and reloading web pages are simply too long to keep up with creative ideation. It is important that your notes app have a web version, to be able to access your notes from other computers, but your primary access will be through a native app. If there is also a native desktop app, this also allows offline access to your notes, and a way to save local backups. 10. Capturing and syncing across multiple devices We live in a multi-device world, and this feature is now a must-have. You might capture most of your notes on a desktop computer, but having a mobile app for photos and videos will add a lot of richness and depth to your collection of notes. Reading ebooks on an iPad, I find that having my notes app just a few taps away is invaluable for capturing my ideas. Although some apps allow you to set up sync manually, using third-party services, I don’t recommend it. Leave this technically complex task to the experts, even if you have to pay a monthly subscription. 11. Exportable as plain text As heavily as I rely on formatting, I believe it is important to at least have an option for exporting notes as plain text. To protect against catastrophic data loss, the company going out of business, or simply because your needs change and a different app better suits your needs. Plain text is the tool of last resort for getting your data out of a piece of software. These should be individual files, not a single, giant database record.

Nice-to-haves 12. Side-by-side viewing This might seem overly specific, but is actually a crucial part of using your notes to do creative work. Being able to compare and contrast two notes, and move information between them if needed, is essential for creative synthesis. This can be accomplished through multiple panels, or by allowing you to open notes in separate windows. 13. Bullets or lists Lists are one of the easiest ways to brainstorm and plan, and a natural fit for informal notes. Although a list can simply be a series of text entries without any particular structure, it’s helpful if there is a bullet, numbering, or list feature that makes it easy to create them. 14. Automatic date stamps Within notebooks or folders, the best way to organize groups of notes is by their date of creation. Our brains naturally understand the flow of time, and often associate ideas with specific events or periods. Choose a notes app that automatically labels each note with the date. 15. Tags Although I am a critic of using tags as a primary organizational system, they are still valuable. Your notes app should allow you to create and apply multiple tags to any given note, giving you an extra layer of control.

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A Maker’s Ethos in the Era of Networked Attention Once upon a time, we faced the scourge of Information Overload. Too many emails with too many details producing too many open loops to keep track of. But now we have a new challenge: the Information Apocalypse. Not only is there far too much information to consume or manage, much of that information has now been weaponized. Whether it’s retargeted ads chasing us across the web, mobile apps designed for addiction, or emotionally charged news hitting us on every channel, it can often feel like we’re living in the informational end times. But I believe that makers have something to offer the broader society in these dark days: an ethos that subordinates information consumption to the act of producing things of objective value. Being a maker today is a radical act. It means treasuring the insightful, the subtle, and the private, in a world that increasingly prizes only the novel, the sensational, and the public. Being a maker requires patience when we’ve been trained to switch our focus constantly. It calls for reflection when we’ve been trained to react. It asks us to revisit an idea again and again until we’ve truly distilled its essence, instead of refreshing a feed for the newest of the new. Mike Caulfield, in his brilliant talk The Garden and the Stream: A Technopastoral (which I will borrow heavily from) argues that our predominant model for the social web – including blogging, Twitter, Facebook, forums, Reddit, Instagram, and others – is fundamentally broken. He makes the case that our survival as a species depends on us “getting past the sweet, salty fat of ‘the web as conversation’ and on to something more timeless, integrative, iterative, something less personal and less self-assertive, something more solitary yet more connected.” This is the way of the maker – to use time to create something timeless, to form something apart so that it can be integrated, to iterate toward perfection, to create in solitude something that will ultimately connect them with others.

It’s tempting to check out, to delete our Facebook account, cripple our devices, and move to a log cabin in the woods. But this is ultimately an abdication of our responsibility. Our responsibility to offer our gifts to the communities that have nourished us. To share what we’ve learned with others coming after us. To participate in our democracy as informed citizens. Being plugged in is a good thing, and there is value in every kind of information stream, from Twitter feeds to philosophy books. A balanced information diet draws from many sources: short and long form, simple and complex, trivial and lofty, familiar and novel. The Informational Apocalypse has little to do with the sheer volume of information we’re consuming. It comes from a diet dominated by the informational equivalent of fast food. Applying the maker mindset to our online behavior and balancing our informational diet with more nourishing ingredients requires shifting our model of the social web, from a Stream to a Garden. The Stream is a constantly flowing, endless succession of “events.” It is not a distinct entity that you can look at, walk around, and examine at your leisure. You can only dive straight into it, feel it flowing around and through you, and feel the force of it hitting you. Everyone’s thoughts and actions in the Stream are collapsed down to a single timeline, curated according to the sole criteria of “engagement” and centered completely on the individual experience. The Stream is everywhere: social media networks are the obvious ones, but it’s also the notifications panel of your smartphone, email, Slack, and text messages. The Stream has become the dominant mode of social interaction via digital means. The Stream has created a global conversation of unprecedented proportions. But there is, of course, a dark side. Everything in the Stream is persuasion, argument, or advocacy. Everything is personal and very urgent. It’s exciting and invigorating. This makes it completely unsuited to many of the uses we put it to. What we need now is a platform for reasoned discussion, for developing ideas slowly over time, and for building solutions to complex challenges. The web we have today is simply not designed for these pursuits. Now imagine a different model for how we use the web: as a Garden. A Garden is a finite space, with integrated parts that evolve slowly and in relationship to each other. It is iterative, with each season arranging and rearranging things. The

Garden is not collapsed down to a single path or sequence. There are many paths through the Garden, many possible meanings, and each time we walk through it we create new ones. We are constantly adding things to the Garden in a serendipitous way that allows many future, unpredictable relationships. In a Garden, it is pointless to ask whether the tree came before the bridge. They are related to each other in a timeless way, and this is true of everything in the garden. Each flower, tree, and bench is curated by the gardener so that visitors can have unique yet coherent experiences as they find their own way. The Garden is a sort of experience generator, capable of infinite expression and meaning. In the Stream, I may scan a headline about gun control that confirms my beliefs, and retweet it with a wry comment. In the Garden, that same article is captured, pruned of everything but the facts, and added to a collection of sources that together form a coherent mental model. This model is not perfectly consistent – some sources will contradict each other. But having such a web of conflicting opinions at my disposal, I have something that is bigger than any single event, any single source, or any single narrative. I have a living model. We’ve been using the web as an instantaneous publishing machine. But it can also be used as a library. You could have copies of every document, book, image, video, or webpage that you’ve found enlightening or interesting, in a form that you control directly. You can edit them, annotate them, add links to them, summarize, and share. These artifacts become tools to think with. This library of personal knowledge is yours to mold as you see fit. You can fill it not only with facts and authoritative answers, but with doubts, with questions, with tenuous connections you haven’t quite yet proven. On the public web, only the author has the authority to say what an idea is associated with. In your private library, your models have time to grow past infancy into whole new ways of thinking and acting. And once it’s ready, then you can share it. Not as a hot take on the news of the day. But as a thingified idea – a technique or theory or framework or product or service – that can stand on its own two feet and have an impact on the world. It can even provide a source of income to fund your future efforts. In this way, humanity can advance, not through argument, but through true collaboration. There’s a funny thing about collaboration. You can’t do it right from the

beginning, or 100% of the time. It requires everyone to go away for a time and work through a challenge in isolation, to develop their skills or ideas as something more than an opinion. It is only when individuals take responsibility for their own work, that they can come together and be responsible as a group. The web as a Garden works quite differently than what we’re used to. It isn’t a web of “hey look at this!” one-hop links. It isn’t just a conversational trail but a web of ideas. It isn’t obsessed with arguing points, but with developing points. It isn’t a series of sealed shut presentations, but a reconfigurable model of understanding. In the Garden, ideas gain value as they age. Makers know how to build Gardens. They know how to consume the new, but subordinate it to the constraints of a craft. They know that genuine agency comes not from indulging every whim, desire, and reactionary impulse, but through voluntary submission. Submission to teachers and mentors, to the standards of their field, and to the public. Skilled practices give makers a tether to reality – a domain in which their own ideas and the ideas of others hold equal weight. Everyone wants to play in the Stream, but it is those who build Gardens that will win the future. And by providing a way out of the Informational Apocalypse, ensure we have a future at all.

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The Maker’s Guide to Content Curation One of the best ways to advance your career, create an extra income stream, or become an entrepreneur is by creating content. By “content” I mean tangible information that delivers value to others, delivered over the Internet. It could take the form of a blog post or a long-form essay, an instructional guide or a how-to video, an ebook or online course. Content is anything you make out of knowledge and ideas, either your own or those of others, that exists on its own as a stand-alone thing. Content typically has the goal of entertaining people, helping them learn something new, or giving them solutions to their problems without you having to be there. Why is creating content such an effective way to advance almost anyone’s career or business? Because it gets you started making things, without many of the risks that are normally required. You gain experience in all stages of the creation process, from first thinking of the idea, to outlining the main points, to trying out different approaches, to refining and editing your “product,” to final delivery. But you get to do all this learning without paying for expensive overhead, like a staff, office rent, or equipment. You don’t need to quit your job or spend years earning a new degree. Creating most kinds of content requires nothing more than a computer or a smartphone to get started. Information products have many similarities to physical products. They both require a process of development and marketing, both need to be produced and delivered, and both can be sold to make money. But information products have a few key differences that make them perfectly suited to getting a business off the ground. First, they can be created out of nothing but thinking and effort. The cost of raw materials is zero. Second, once you’ve produced the first one, they cost nothing to duplicate. The cost of additional manufacturing is zero. Third, they can be stored for free on your computer, and delivered for free over the Internet. Inventory and distribution cost is zero. And fourth, you can easily edit a text, modify an image, or change a

webpage after the fact, often even after they’ve been delivered. The costs of modification are zero. That last one is actually the most important. Because early on, your biggest challenge is knowing what to create. You may have lots of ideas of what you think people would want, but until you actually have the money in hand, you can’t be completely sure. The biggest risk with physical products is that you have to spend a lot of money upfront – raw materials, design, manufacturing, storage, distribution, marketing – before you have the first opportunity to discover whether people truly want it. But content creation almost eliminates this risk, because all these costs are virtually zero. You can create a piece of content in a few hours or days, post it online, and get immediate feedback on whether it meets people’s needs. If it does, you simply keep duplicating and selling it. If it doesn’t, you can make changes in a matter of minutes and republish it as a “new and improved” version! And this is only the beginning of the advantages of selling content in the form of information products. The marketing and sales of information products is also much easier. Because the costs of production and distribution are zero, you can run sales with heavy discounts, bundle with other products, provide free trials, partner with other content creators, and give free copies to influencers for exposure. There are limits to these tactics for physical products, because you have to recoup your costs. But with information products, any money you make on an additional copy is pure profit. Therefore, any price above zero is profitable. Even with free giveaways, at least you’re not losing money. Information products can easily be purchased online without any involvement on your part. The income is largely passive, meaning you can turn your attention to the next thing without immediately losing your source of income. You can also market new products to the audience you’ve already built, because online purchases allow you to collect customer email addresses, and it again costs nothing to contact them with new offerings. But let’s take a step back: how do you start creating content if that’s not something you’ve done before? One of the best ways to start creating content is to curate content. Curation is the process of sorting through the vast amount of content from others that already

exists, and picking and choosing the best or most interesting items. Think of the curator in a museum, who sorts through thousands of paintings or artifacts to pick the select few that will make it into the exhibition. Or the editor-in-chief of a newspaper, who chooses from among hundreds of things that happened in the last week, to pick only a few that will be published. But choosing the items is just the beginning of a curator’s job. They also organize and present the items they are curating in a way that makes sense. The museum curator might present the works of an artist chronologically, or according to certain themes, or based on their historical importance. A newspaper editor might put urgent news on the front page, investigative reporting further back, and special interest stories next to related ones. In many cases, the curator’s job goes even beyond that, including annotating, explaining, or putting the items into a narrative. Museums often present a brief introduction to the exhibition, printed on the wall by the entrance. Individual pieces often have little wall plaques explaining what the piece is about, the context in which it was created, and its historical significance. In addition to shaping the stories according to what they think is important, newspaper editors often write “editorials,” offering their opinions or interpretations on recent events. Can you see how the job of choosing and organizing items to present can very easily turn into creating content of your own? There is not as much of a difference between curating the work of others and creating your own as you might think. The act of presenting the works of others is not a passive one. It requires a strong background in the field, sensitivity and creativity, and the best curation is one with a strong point of view on what is most relevant. As a curator, your reputation and your skills are on the line, and this is what makes it a form of creation in itself. Would you like to write poetry and self-publish a series of poetry books? Before you have the courage to publish your own, curate the best poems you read into a monthly newsletter that you send out to subscribers. Are you interested in covering a niche topic like home breweries as a freelance journalist? Start by filming short videos of yourself with your smartphone, in which you talk about the most interesting events you attended recently, and post them to YouTube.

Would you love to be a fashion influencer, and get paid to try out all the latest brands and styles? Start with a Tumblr where you post links from all the best fashion gurus you follow, with your opinion on whether you agree or disagree with their recommendations. Here are some other examples of things you can create as a curator: Curated news feed: find the best sources of news on a particular topic, and filter only the best ones for others Diagrams, infographics, other visuals: make a map or diagram showing the best tools, websites, events, or products for a particular hobby or activity, and how they relate to each other Comparison tables: if you’ve done the research comparing the options in an industry or niche hobby, create a table showing how they compare Crowdsourced toolkits: talk to the leading experts in a niche and ask them for their favorite tools, and summarize the results Guides: if you understand an industry or a field, create a “guide” that shows people who the major players are, or what the best sources of insights are Curated video channels: collect the best videos on a topic and share them on your YouTube channel, with some commentary on why you think they’re so good Expert directories: create a list of the top experts in a field for people to follow Web page showcase: publish a collection of the best websites, or individual web pages for a particular topic

Slideshows: create a slide presentation of the best examples or models, and upload it to a site like Slideshare Learning curriculum: make a “curriculum” of the best sources of learning for your field, along with some commentary on how people should use them and in what order Review videos: make short videos reviewing or critiquing works or products in your field, adding your perspective and personality to the mix Event guides: make a calendar or directory of the best events (concerts, festivals, conferences, meetups, trade shows) you’ve found Open questions list: share a list of the most interesting or important open questions in your field, to help newcomers orient to the current landscape Galleries: publish a collection of the best images you’ve encountered, along with links to their creators’ pages All these formats ultimately boil down to different combinations of text, images, and video, which can be delivered and monetized in different ways: Create a PDF and sell it directly on your website using Gumroad Start a blog on WordPress and charge for some of the articles using Memberful or Patreon Publish your work for free and take donations using Paypal Publish a course on Teachable or Thinkific and charge for access Create a profile on Clarity and charge by the minute for phone calls, using your content to market your expertise

Create a paid email newsletter using Revue and distribute it via Mailchimp Set up an online forum using Discourse and charge for access You may not be familiar with the platforms described above, but this doesn’t have to be a massive new endeavor. In fact, I would bet that you’re already doing most of the work required. The average Facebook user publishes 90 “status updates” per month. With a little extra work, many of these could be considered small bits of content. As a novice, you’re probably already consuming a lot of content from others and learning a lot for yourself. That’s the perfect opportunity to turn around and share with others what you’ve just learned, perhaps with some tips on how to avoid the mistakes that you’ve made. Give them a shortcut to the small outcomes you’ve already achieved, and you’ll be amazed how grateful they will be. Most people think that you have to be an established expert to sell your ideas and advice to others. But this is the furthest thing from the truth. People prefer to learn from those who are within reach, who only recently walked the path that they are trying to walk. There will always be mega-celebrities who people aspire to, but when it comes to actually getting their hands dirty, they usually go to smaller, more approachable practitioners who they can relate to. By starting with curating the content of others, you accomplish a few things with minimal risk. You develop your taste, as you learn to distinguish what is great from what is merely good. You start to connect with existing audiences, as established creators have their own pages and communities you can interact with. And you even begin to see what is missing or not working about existing content, as you listen to the comments and complaints online. And you do all this with minimal risk, because you’re still only showing the work of others! Sometimes, you can even offer your first information products as repackaged or reinterpreted versions of existing, successful products. This allows you to skip the whole development and testing process, and sell directly to an existing audience that’s already receptive to your message. My first online course, Get Stuff Done Like a Boss, is a video-based version of the best-selling GTD productivity method by David Allen. I knew millions of people had read and loved the book, but many like me had trouble implementing

its methods without a step-by-step, visual guide. My initial goal was to make $1,000 dollars and have 100 people take my course. More than 4 years later, more than 15,000 people have taken the course and it continues to be the perfect introduction to my work for new customers, despite the fact that it’s not even my own ideas! Our products not only don’t compete, they are actually complementary: my best customers are those who have already read the GTD book but need to see real examples, and those who start with my course often go on to buy the book. You have to be careful to respect copyrights and give credit, but surprisingly often, established experts are happy for the extra exposure and will even share your stuff. Several years after launch, David Allen had me on his podcast as a guest because he liked how I taught his methods! The truth is, the very idea of an “established expert” is under attack. Every field and industry and community, online and offline, is undergoing dramatic changes. Whether it’s technological disruption, globalization and automation, demographic or inter-generational shifts, or something else. Every time a new trend arises or a new skill becomes valuable, there is an enormous opportunity to take the role of an authority and leader. The greatest Bitcoin expert doesn’t have more than 10 years of experience. The most experienced virtual reality experts have only been working on it for a few years. The changing world is leveling the playing field and turning us all into amateurs at an unbelievable pace. This is why the role of the curator is getting more and more important at this point in history. The other impact of content creation becoming so easy is that people are faced with a deluge of new information every time they turn on their devices. More than ever, they are looking for interpreters and narrators to tell them what it means and how to make use of it. Framing people’s options in a way that restricts their choices can help them see those choices more clearly instead of overwhelming them. Even in small niches, like indoor gardening, making your own jewelry, or ultimate frisbee, there is far too much material for a novice to make sense of. Your curated recommendations and reviews can serve as a valuable access point for those who don’t want to spend as much time on it as you have, which is nearly everyone. But you have to go beyond just collecting a bunch of links – social media has solved the problem of discovery for good. You need to add an extra layer of value, giving people the context and perspective that only comes

with true understanding. This article has focused mostly on those who want to create a new product or business. But I believe that curation will increasingly be an important part of everyone’s job, not just solopreneurs and makers. Even if you never plan on sharing content with anyone, you still need to know how to curate content for yourself. The only way to escape the tsunami of information overload is by making intentional decisions about what to pay attention to, and what to ignore. Curation has evolved from a specialized profession, to a simple matter of staying informed about your field, and ultimately being more effective at your job. A quickly changing world requires that we take control of our own education, that we weave together our own curriculum from the countless sources we find online. The basic skill required to do this effectively is judgment. And judgment is exactly what curation helps you develop: every time you make a decision, choosing one article or phrase or image or news story over another – you are refining your judgment about what matters and what doesn’t. Sources: this series borrows a lot of ideas and phrases from Austin Kleon’s Show Your Work (affiliate link), Daniel Pink’s To Sell is Human (affiliate link), and Brendon Burchard’s The Millionaire Messenger (affiliate link). In other words, this article curates and summarizes their work!

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The 7 Pillars of Content Curation In The Maker’s Guide to Content Curation, I argued that curating the content of others was an excellent way to start creating content of one’s own, whether your goal is advancing your career or starting a business. Now I want to answer the question: how exactly do I curate content? There are 7 core pillars I’ve settled on: 1. 2. 3. 4. 5. 6. 7.

Create a repository of valuable, pre-selected material Learn (and fail) in public Weave the personal and the objective Provide value back to the people you curate Always be pitching something Feed and tune your network Curate for yourself

1. Create a repository of valuable, pre-selected material This is probably the most fundamental lesson, not only for content curation but for knowledge work in general. It’s impossible to curate effectively just by sharing things on social media as you come across them. There’s no chance that you’ll know whether something is “the best” if you’re evaluating it in isolation. The value you provide is putting it into a broader context or narrative. And that requires collecting things in a repository before sharing them. In 16th and 17th century Europe, it was fashionable for the wealthy and educated to keep a Wunderkammern, a “wonder chamber” or “cabinet of curiosities,” in their homes. These rooms were filled with interesting or rare artifacts – books, skeletons, jewels, shells, art, plants, minerals, taxidermy specimens, stones – from around the world. They were demonstrations of their owner’s intellect and hunger for knowledge. These collections were the precursors to modern museums, as places dedicated to the study of history, nature, and the arts. You should do the same with your personal knowledge collection. Start by collecting a small set of valuable sources and personal insights for your own use. As it gains in size and value, start opening it to friends and colleagues. Eventually, you’ll have so much material that you can create “virtual exhibitions” for sharing publicly, which can be nothing more than websites, image galleries, or downloadable PDFs.

2. Learn (and fail) in public One of the best ways of thinking about curation is that you are “open-sourcing your learning process.” Pick something that you would really like to learn, and make a commitment to learning it in public, including your mistakes. By sharing your learning journey, you create an audience and a community around your learning, at times providing encouragement and other times commiseration. Seeing that others can benefit from your mistakes makes it much easier to recover from them, to push forward, and to take on bigger challenges than you would on your own. Austin Kleon puts it perfectly in his book Show Your Work (affiliate link): “Become a documentarian of what you do. Start a work journal: Write your thoughts down in a notebook, or speak them into an audio recorder. Keep a scrapbook. Take a lot of photographs of your work at different stages in your process. Shoot video of you working. This isn’t about making art, it’s about simply keeping track of what’s going on around you. Take advantage of all the cheap, easy tools at your disposal—these days, most of us carry a fully functional multimedia studio around in our smartphones…Once a day, after you’ve done your day’s work, go back to your documentation and find one little piece of your process that you can share.” The learning process is the perfect thing to share: it is constantly throwing off little odds and ends that can be posted online; it’s ok if it’s messy and incomplete; it shows evidence of consistent progress; it includes both successes and failures; and it makes reference to the best sources while also injecting your own voice and experience. As soon as you learn something, no matter how small, you can turn around and share it with others. This helps you test your understanding, surface doubts or weak points, and gives you an excuse to package up helpful resources like reading lists or walkthrough videos. These resources will be the perfect reference materials for your future self.

3. Weave the personal and the objective Most people share either purely personal updates of no durable value (what they ate for lunch, their workout outfit, or a rant on the topic of the day), or completely objective, but boring factoids (a newspaper article, a link to a website, or a quote from a book with no explanation). As a curator, you should split the difference, sharing content that has inherent value for others, while also adding your own interpretation or commentary. You want to get people used to hearing and valuing your take on the subject, apart from the plain facts. When something new happens in your field, you want people to wonder “I wonder what [insert your name] thinks about this?” This way, every event of significance becomes a trigger for people to seek you out. Kleon has a wonderful set of questions to get you started in the curation game: Where do you get your inspiration? What sorts of things do you fill your head with? What do you read? Do you subscribe to anything? What sites do you visit on the Internet? What music do you listen to? What movies do you see? Do you look at art? What do you collect? What’s inside your scrapbook? What do you pin to the corkboard above your desk? What do you stick on your refrigerator? Who’s done work that you admire?

Who do you steal ideas from? Do you have any heroes? Who do you follow online? Who are the practitioners you look up to in your field? It takes surprisingly little to add your own spin or lens on an event. As Alison Bechdel says, “Whatever we say, we’re always talking about ourselves.”

4. Provide value back to the people you curate As a curator, it’s easy to see yourself as a small fish, especially when comparing yourself to the celebrity experts you are covering. But don’t underestimate your importance – curators and critics are a critical piece of building influence online. There is a limit to how much an established expert can talk themselves up and recommend their own expertise. We’re a skeptical generation that doesn’t take self-promotion at face value. Such experts rely on third parties that they don’t pay or control to give honest assessments of their credibility. It is a major milestone for them to have even one significant curator of their work. You could very well be that milestone for them! How do you provide value to someone who has already seemingly “made it”? There are so many ways. Write them an honest testimonial or review, and post it somewhere that potential customers might see it. Quote or summarize their ideas, and link your readers to the original source. Compare and contrast their offerings with their competitors, which helps filter for people most likely to be served by them. Convert their content into new forms and share them, which will help it reach new audiences. Established experts often care most about seeing their ideas spread and have an impact. They’ll often bend over backwards, provide access to their audience, and even actively promote you if you help them do that. They usually started as curators themselves, and will want to pay it forward however they can.

5. Always be pitching something In the past, the job of a salesperson was to provide useful information. Because the information required to make good decisions was so hard to find, they became gatekeepers of this knowledge and faced little competition. But with the abundance of information available online to anyone with a smartphone, the playing field has been leveled. The customer walking in the door may very well know more than the salesperson about the product. Salespeople must now be skilled at curating that abundance of knowledge with honesty and skill. They earn their commission when they frame the options in a way that makes them less overwhelming to the customer. You may be thinking, “But I’m not a salesperson…” Think again. In a world of fragmented attention, every email, text message, and phone call is a pitch for someone’s attention. Every action you want someone to take – to give you feedback on your draft, brainstorm solutions to a problem, design a website – is a pitch for their precious time, in competition with hundreds of other pitches they receive every day. The first time you ask for money for something you’ve created is an exhilarating experience. It feels like the sky is going to fall, or the authorities are going to call and accuse you of fraud. But long before you’re ready for that, you can practice by pitching other things. You heard me right: pitch other people’s products and services that you’ve tried and enjoyed; pitch books and articles you’ve found valuable; pitch people on trying new things or pursuing new interests; pitch them on rethinking or improving an aspect of their lives. Every time you write an article, post a social media update, or meet someone for coffee, try pitching them on something you think will benefit them. By the time you’re ready to make pitches of your own, you’ll be a sales pro.

6. Feed and tune your network It’s easy to see the world of influencers and thought leaders and to think it’s a solitary affair. The spotlight of “personal branding” shines only on the individual, but in reality it is a community of creative people that produces great ideas and great works. Take Leonardo da Vinci’s famous drawing Vitruvian Man, depicting the essential symmetry and proportions of the human body. It is a symbol of individualism, yet Da Vinci was heavily influenced by multiple others in creating it: the Roman architect Vitruvius, Renaissance architect Giacomo Andrea de Ferrara, and Sienese architect Francesco di Giorgio. Don’t see yourself as a solitary curator lobbing your ideas into the void. Think of yourself as the Head Gardener in charge of an “ecology of talent.” It’s not your job to make everything happen. It’s your job to synchronize an interesting group of people who are passionate about something, and to help them create something together. Your content is just an excuse for this group to form. Doing this work in collaboration with others who can appreciate it is the only thing that makes it sustainable or worth doing. Howard Rheingold calls this “tuning and feeding your network.” Share the things you love and value, and the people that love and value those same things will find you. Do the work, and share the best nuggets with your audience in a format they can easily digest and apply. You don’t want the most followers. You want the best followers. Before you have fans, you must be a fan yourself. As artist Wayne White says, “Sometimes you don’t always know what you’ve got. It really does need a little social chemistry to make it show itself to you sometimes.”

7. Curate for yourself Let’s loop back to the beginning, to curating a collection of knowledge for yourself. As much as I advocate providing value to others, I believe that for this process to truly be sustainable, it has to be inherently enjoyable for you. The harsh reality is that you probably won’t succeed. It’s just a numbers game. Statistically speaking, you probably won’t keep going past a few weeks, probably won’t find an audience, probably won’t ever create your own content, probably won’t make any money, and almost certainly won’t ever build any kind of business out of this activity. At the end of the day, it has to be something worth doing anyway. You have to inherently enjoy most of the experience of diving deep into a small niche, of immersing yourself in its questions and communities, of trying things and failing again and again, of pulling a nugget of insight out of the chaos to bring back to your tribe. This is why the job of curator is reserved for the truly passionate, who would do what they do even if no one was listening. You can view the curation process as a conversation you have with your future self. Whether it’s writing your reveries in a diary or choosing photos from a family vacation, you are sending these like packages forward through time. Your future self will most likely receive them, and there will be an impact. It might make them happy or sad, nostalgic or grateful, excited or somber. Use this conversation across time to learn to tell your story. Use it to understand your own evolution. Use it to map your patterns of learning and thinking over time. Personal curation is the pursuit of self-understanding, using tangible or digital artifacts as mirrors into our deepest selves.

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RandomNote: Building an Idea Generator What if you could push a button and immediately be given an idea? Not just any idea. A good idea. An idea relevant to your interests, your goals, and your current projects. What if every time you pushed this button, you also made it more likely that even better ideas would be surfaced in the future? I’ve found a way. It started when I began thinking about ways to inject randomness into my workflow. Books like Antifragile, Seeing Like a State, and Incomplete Nature have given me a deep appreciation for the power of randomness to produce resilience, strength, and creativity. But it’s difficult to program randomness, to schedule it in a neat slot in your calendar. By its very definition it seems to resist attempts at control. It lurks like a predator on the periphery of our thinking, showing up as entropy, the force we are always fighting. In my online course, Building a Second Brain, I teach various methods of retrieving ideas from a digital note-taking program. We explore proven techniques for outlining, planning, categorizing, summarizing, searching, filtering, prioritizing, commenting on, tracking, hacking, reframing, restructuring, redesigning, and scaling up or down the scope of the notes in your collection. But all these diverse methods have a common theme: they rely on imposing order on information to make it more legible. This gives them a common weakness: they cannot benefit from unexpected surprises, from serendipity. They all operate on the assumption that ever-increasing order will always make your ideas better. As our world gets more complex, chaotic, and unpredictable, this assumption

gets riskier and riskier. The downsides of not benefitting from randomness become ever greater. That’s because the greatest breakthroughs usually come from connections that are unexpected, unusual, and unorthodox. When we impose too much order on our ideas, it is these very connections that slip through the cracks. Injecting pure randomness into your work is easy. Just do a Google search for a random word every day. Turn to a random page of the dictionary as a brainstorming exercise. Even horoscopes are a form of using random information to stimulate insights. These methods have their place. But I wanted to make randomness a part of my workflow. I wanted it to be an operational, tactical tool. This requires limiting the scope: providing small nudges and constraints to increase the chance that whatever gets surfaced is relevant to my needs right now.

The web app I worked with Benjamin Mosior to write a script with a simple function: show me a random note from my Evernote collection. I later worked with Chris Galtenberg and Callum Flack to turn it into a simple web app that anyone can use. You can try it by visiting this link and logging in to your Evernote account: Try RandomNote Clicking the green icon at the top left will show you a note drawn randomly from your Evernote collection.

My experience When I first started using this web app, I figured it would become part of my weekly review. An infrequent, only occasionally useful exercise to remember notes I’d previously saved. What I’ve found has been very different. I use the app probably 20–30 times each day, after setting it as my default homepage, and as a result my whole conception of the relationship between memory, ideation, and creativity has changed. Let me try to explain what I think is happening. First, I believe that this little app activates many of the same triggers and habits normally targeted by social media. About half of the time I previously spent on social media is now spent looking at, modifying, and deleting old notes. I think there is something about the human mind that requires micro-breaks — brief flashes of attention on something different, something new, something a little stimulating. The usual default is social media apps, which quickly suck us in with their seductive, never-ending feeds. What if this tendency to occasionally scan the environment was treated as an opportunity, not a threat? I’ve noticed that often all I need to make a decision or see a solution is to switch my attention to something else for just a moment. I find my mind drifting toward Twitter, but seeing the random note pop up hijacks that instinct, leading me instead back into my best thinking. Second, randomly surfacing notes provides many, many more chances than usual to tweak, add to, or summarize notes. Using notes opportunistically in the way I recommend requires that you have many such encounters. Many of the notes that get surfaced I retitle, tag, move, or delete, which means I’m constantly pruning and curating my collection for my future self. Every interaction with my notes serves a dual purpose: giving me ideas now, and giving me even more condensed ideas in the future. This is tremendously rewarding. Addicting even. The paradox at the heart of managing notes is that the moment you get familiar enough with a note to know what it’s about, you also lose the objectivity to know which changes to make. By quickly flashing notes in front of me, I’m able

to make quick, intuitive judgments about how to make them more discoverable or understandable, before my inner critic kicks in and starts nitpicking the spelling and punctuation. Third, what this little app has reinforced for me is that it’s much, much more powerful to know that a note exists and what it’s generally about, than to know exactly what it contains. This is what differentiates this practice from spaced repetition (systematically surfacing notes just as you’re about to forget them): I want to remember as little as possible, not as much as possible. Every idea I’ve offloaded to my Second Brain for storage, frees up a little bandwidth in my first brain for thinking. What I do when a note appears is get the gist. This is greatly facilitated by Progressive Summarization, because it allows me to jump to only the most relevant parts I’ve identified in advance. If these parts are relevant to a problem at hand, I may add another layer of summarization, or move this note to an active project notebook, or add a link to it to my task manager, or send it to someone I know it would be useful for, or tweet it. In other words, further interaction that is further embedding the information in my thinking. I’m not seeking to load the contents of this note into long-term memory or even short-term memory. I don’t want to remember it or even fully understand it. If I’m going to use my most limited resource — thinking bandwidth — it had better be spent relieving the demands on future thinking bandwidth. One of the few things worth sending through the bottleneck is tasks that add capacity to the bottleneck. This is how flywheels are made. Fourth, there’s something magical about just the right level of relevance and actionability. Because I’m randomly surfacing notes that I have previously judged to be valuable, anything that comes up seems interesting. All the work I’ve done to sort notebooks into stacks, notes into notebooks, and to add layers of summarization pays off in a huge way when these notes randomly appear close together, like magnets suddenly reaching proximity and snapping together. The signal in the noise of each note trains you to look for certain patterns, making the signals in other notes that much easier to detect.

An experiment Let’s do a little experiment. I’ll post links to the next 10 notes I randomly surface using the RandomNote app, with a brief commentary on what they give me. #1 Fooled by Randomness book notes Coincidentally, the very first note is from a book by Taleb, the author I mentioned previously. I find that such “coincidences” occur continuously now. This quote is a good reminder of the power of satisficing, which I can always use. #2 Screen Shot 2015-11-11 at 3.56.37 PM I have no idea where this comes from, but I remember why I saved it — it’s an example of how a mere background can evoke meaning, not just look pretty. #3 Spritz QS talk My notes on a talk I watched on the Spritz high-speed reading method. A friend just mentioned this to me this past weekend. This note is a good reminder of “what I know” about it. #4 Two types of emergence My notes on a source I read for a blog post about emergence, from over a year ago. This reminds me to continue my reading on emergence, as there’s still so much left to explore. #5 Episode 1: Tiago Forte – RadReads This is a webclip of a podcast I did recently with Khe Hy. I save these purely for archival purposes, but it’s a good reminder to catch up with Khe soon. #6 Fidelis Education Another webclip, of the website of a “Learning Relationship Management” company I got a demo from about two years ago. I’m sure the site is out of date by now, but this prompts me to check in with them to see if there’s anything new. #7 Additional Notes on “Drawing Dynamic Visualizations”

Another “coincidence” — I’d just been experimenting with Tableau to make data visualizations for an upcoming blog post. This is a good reminder that I have some existing notes on the topic. #8 The future of biosensing wearables « Rock Health I can see from the notebook this is in that it was from a long-past research project. I can either move this into the Archive notebook for that project, or just delete it as it’s no longer relevant. #9 What’s the best, most effective way to take notes? notes Whoa! This is what I call a “strike” (as in finding gold) — a high-value, wellstructured and summarized note highly relevant to a current project. I’ll move this to the Building a Second Brain notebook. #10 Notes on sleep from 4HB A few small notes from the book The Four-Hour Body. Not much of relevance here. It’s a miss, but I’ll keep it. What you may have noticed is that a variety of things can spring from my interaction with these notes, however brief: a new idea, a new version of an old idea, an old version of a new idea, a decision, a memory, an immediate action, a future action, a question, an open loop, etc. There’s no formula here. No checklist that could produce this serendipity on demand. This is non-linear action and reaction: many times the seemingly least important note (the business card of a used car salesperson) activates the most important or urgent open loop (I need to get my oil changed!). Hierarchies of importance break down, freeing you to look everywhere for insight. The sense of possibility starts to increase as you realize the quality of the final output has very little to do with the brilliance of the original idea. You can use anything. I have the gratifying sense that I am navigating a system bigger than myself. It is not fully under my control, but that means it is released from the bottlenecks of my time, my intelligence, and my attention. I am the conductor, not the whole orchestra.

Building systems for externalizing your thinking is not about better, faster, stronger. It is about getting out of your own way, gaining more control by letting go of inferior forms of control.

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Desktop Zero: An Experiment on Clearing My Digital Workspace I performed a little experiment this month, to test my hypothesis that a number of useful files accumulate on the desktop and are worth saving for the long term. The experiment was simple: I allowed files and folders to accumulate on my desktop from October 1st to 30th, without organizing or filing any of them On Oct. 30 I went through them and analyzed their contents to see whether the files were of long-term value

8: A terrifying screenshot of how my desktop looked after a month of letting files accumulate there

Here are the results:

156 files and 5 folders accumulated, with a total size of 2.2 gigabytes File types included: 5 folders (from images I exported from slide presentations, since it creates a new folder with each export) 2 design files Text expander snippets file 1 audio file 5 html files 135 image files 1 slide presentation 1 video file 9 PDFs 1 text file (because virtually all text I store directly in Evernote) It took me 23 minutes to file all 161 items in my PARA system in Evernote and my Documents folder (which syncs automatically with Google Drive)

9: How I arrange my windows for side-by-side for filing

As I reviewed each item, I categorized them by low, medium, or high value to determine whether these were the kinds of files worth keeping and filing.

Low value These items were low value mostly because I had other places I could find them if needed, such as my email, source files, websites, or cloud storage. They made up about 75% of the items, and I deleted them immediately in large groups using command-shift-click to select multiple items, and command-delete to send them to the trash. Contents: PDF of academic paper I read and took notes on (already added as an attachment to an Evernote note) Screenshots of PDF diagrams (already added to notes) Images from online articles (already used) Screenshots used for troubleshooting/email explanations (can find in email if needed) Slide images/screenshots for book manuscript (added to Google Doc) Screenshots taken for social media/blog posts (already published) Photos for online photo galleries (already published)

Medium value These items could probably be found elsewhere, but they were relatively important and I might need to reference them again. They made up most of the remaining items, and I filed them in my PARA system, mostly under Areas. Contents: Signed change of address form for tax prep service 3 401k plan documents ETF form for life insurance payments Video and audio from recorded interviews (always good to save in case they disappear from online hosting) Photos gathered and organized for a blog post (which I may need to use again for followup articles) PDF about information overload someone sent me (which I’d like to read)

High value These two items either related to active projects that I needed to take action on (banner image) or took some effort to produce (Facebook data archive). I put some extra thought into how I labeled and filed them, one in a project and another in an area. Contents: Banner image for promoting upcoming workshop (reminding me to promote it) Facebook data archive export (downloaded to create a photo album of my 6 years in the Bay Area, and saved as a backup)

Takeaways I’ve always made a habit of clearing my desktop and downloads folder on a weekly basis, since they are like the “inboxes” to my digital life. Because most files downloaded from websites, saved by software programs, or exported from source files tend to be saved here by default, a diverse mix of digital assets tends to accumulate quickly. I think there are three primary benefits to doing this, and the actual storage of the file is the least important one:

1. Reminds me of actions I need to take 2. Keeps my workspace clear for incoming inputs 3. Saves files for future reference Only a tiny percentage of accumulated files remind me to take an action, since I’m pretty good at capturing open loops before this point. But even that tiny percentage can yield large benefits. In this case, I am flying to São Paulo in a few days to deliver a full-day workshop, and remembering to promote it to my audience could have a significant impact on its success. Just as importantly, I noticed that having so many files lurking in the background produced a kind of psychological noise. Even though I rarely saw them behind the application windows, the effect was similar to having a messy desk. Often I went looking for a file I had saved to the desktop, and had to wade through the morass to do so. My conclusion is that it is absolutely worth clearing your desktop and download folders on a semi-regular basis. A great way to do this is to make it part of a Weekly Review, so that you’re doing it in big batches, which saves time.

10: My Downloads folder (on the right) after clearing it, and my Documents folder (on the left) with my PARA folders.

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Tide Turners: A Workshop on Using Business to Fuel Spiritual Awakening At the end of July, I participated in a two-day workshop in San Francisco called Tide Turners. This is the story of what I discovered there. I first met Joe Hudson, the creator and leader of the program, at a Consciousness Hacking meetup dedicated to building products that contribute to self-awareness and sustainability. He led a short conversation at the end of the evening with a group of people that stuck around afterward, and I was impressed by his presence and vulnerability. Joe doesn’t have the typical background of a self-help guru. He is the founder and managing director of One Earth Capital, a boutique venture capital firm that invests in early-stage companies developing “decentralized, game-changing technologies in transformative personal development.” This includes businesses working in executive coaching, sustainable agriculture, and financial services. As explained on his website, his teacher and mentor was Cees De Bruin, a Dutch investor and entrepreneur who had a way of asking questions and getting to the root cause of the challenges that people faced in their lives and businesses. Joe describes his initial fascination at watching how De Bruin combined deep empathy and compassion for people, with an uncanny salesmanship ability: “One day, I watched Cees, a quirky guy from Amsterdam, talk to an American farmer. He sat and asked questions and at the end of their conversation, the farmer wanted to buy the product that Cees was selling. Cees never tried to convince him into anything. The sale was a natural progression of events that stemmed from their conversation that led the farmer to realize things about himself he hadn’t before. Once the connection was made, the sale was done. This progression fascinated me and I wanted to learn more. Over my time spent with Cees, I saw this gift over and over again.” His time with De Bruin was part of Joe’s 20-year spiritual odyssey through meditation, Eastern philosophy, neuroscience, psychology, and purpose-driven business. Tide Turners and his other courses are his attempt to integrate and teach what he has learned to leaders and founders doing important work.

Beginning the journey A few weeks earlier, a friend told me he had completed the Tide Turners workshop just a few months before. As I waffled and wavered over whether I would take the plunge, he leaned over, looked me straight in the eye, and told me decisively that I needed to do it. He recommended it as the most impactful personal growth experience of his life, and had the results to match. I decided to enroll then and there. From the very beginning, Tide Turners was unlike any other “self-development program” I’d ever experienced. Typically, workshops are held in corporatelooking office spaces or hotel convention rooms. Our course was held in a beautiful mansion at the edge of Alamo Square in the hills of San Francisco, with modern, clean interior decoration and lots of light. There were no sign-in forms, introductory videos, or seating arrangements. It felt more like going to a dinner party at a friend’s house. About 25 people showed up, and we sat in chairs arranged in a single large circle in the living room of the house. The participants were of different ages and backgrounds, but there was a solid majority of young, Silicon Valley tech professionals and founders. What they seemed to have in common as we shared our goals for the weekend was a big vision for something they wanted to create in the world, and a track record of using personal development as a path to get there. My goals for the workshop, scrawled hastily in my notebook in the minutes before we got started, were simple:

1. Discover my next area for growth as a leader 2. Usher in the next stage of evolution of Forte Labs 3. Found Building a Second Brain as a movement In other words, my priorities were myself, then my business, then my work. During the weekend I would discover just how many layers there were to these seemingly simple goals. The official learning objective of the workshop is straightforward and practical: “Bringing awareness to how our consciousness affects our communication and

learning techniques to become more effective in the following areas: fundraising and sales, product development, customer service, attracting great talent, and managing teams.” But there is a deeper, more intriguing story to Joe’s work. One of the most fundamental assumptions in modern society is: that you can either be spiritual and have inner peace, OR live a successful life with material rewards. But not both. Joe is seeking to show that the most worldly experiences, such as in business, can fuel profound spiritual awakenings. That what we think of as competing priorities can actually be complements. Paraphrasing from the Tide Turners website, Joe believes that the experience of oneness with the universe that is the goal of so many spiritual traditions is not an endpoint, but a starting point. From there, we naturally ask how we can work from that place of oneness, start and grow businesses from oneness, have relationships in oneness, create community in oneness, and parent from oneness. His intention is to discover how the journey of self-realization can be one and the same as the journey of living an effective, successful life. These intentions resonated deeply with me. It is very much the same thing that I am seeking in my work, except I had never stated them so explicitly. As we finished our brief introductions and began the exercises that would take up most of the weekend, I began to sense that I was going to uncover something very profound and powerful in this course. I decided to maintain as open a mind as possible toward what that might be. The basic methodology that Joe teaches is called VIEW, which stands for Vulnerability, Impartiality, Empathy, and Wonder. But like all frameworks, the power is not in the framework, but in how each of these “modes of being” are embodied. The weekend was dedicated to experimenting for ourselves what it meant to stay “within the VIEW”, spread out over two days of conversations, exercises, and activities.

Vulnerability: the courage to question what keeps you separate from others The first exercise was in pairs, each person sitting in a chair facing their partner knee-to-knee. It was an eye-gazing exercise, designed to break the ice and help us begin letting our guards down. Sitting face-to-face, I felt a slight twinge of anxiety as I stared into the eyes of a stranger that I knew was about to see behind the curtains of my well-ordered life. For the second exercise, they asked one partner to stay silent, while the other verbalized the emotions or impressions that they felt they were receiving as they locked eyes. In conversation, I usually try to stay fairly impassive and “neutral,” not wanting to react prematurely or give away what I’m thinking. I’ve always thought that this made me a “good listener,” so I was shocked to hear the unfiltered stream of impressions of me from my partner: frustrated, annoyed, angry, bored, judgmental, distracted. I learned in this exercise that I put a tremendous amount of energy into not “giving anything away,” but that this just makes me come across as withdrawn and uninterested, if not outright hostile. I think I’m being stoic, when in fact I’m being cold. Then when they react negatively to this coldness, my story that people aren’t interested in me or what I’m doing is confirmed. A self-fulfilling prophecy, like all stories. Through these simple exercises I began to learn what was meant by the V for Vulnerability in the VIEW framework. I had understood vulnerability as something akin to embarrassment, a collapsed definition that I suspect has roots in my conservative Northern Italian (by way of Brazil) upbringing. I had a trick for being vulnerable when I wanted to be – just say something embarrassing – but this was a poor substitute for the real thing, and often backfired for obvious reasons. On day 1 I learned that vulnerability is more like a growth edge, one that is unique for every person and constantly shifting from moment to moment. A topic or conversation that is vulnerable in one context may not be vulnerable at all in a different context. Your growth edge is whatever is on the edge of comfort for you in a given moment. You can’t identify it using a checklist or algorithm,

because by the time you do, the moment will have passed. You can only sense it, like a shifting chasm you are trying to communicate across. And you only have a moment to decide whether to jump, before it passes. For the third exercise, we got into pairs again, this time to trigger each other on purpose. A collective groan of discomfort passed through the room as we were instructed to ask our partner what they least wanted to hear in the world, and then to say it to them to their face: “You’re not good enough”; “You’re not going to make it”; “You are ugly”; “Your business is never going to succeed”; “You’ll always be alone.” The purpose of this exercise was to begin practicing the core technique of the VIEW framework: How/What questions. On the surface, this is very simple: ask questions of your conversation partner that begin with “How…?” and “What…?” That is, questions that invite open-ended, constructive answers, rather than “Why…?” questions that demand justifications or “Do you…?” questions with yes/no answers. Instead of “Do you love your partner?” you ask “What would it look like for your relationship to thrive?” Instead of “Why do you want to quit your job?” you ask “How could your job satisfy all your needs?” Instead of “Which one do you care about more?” you ask “How could you have both?” The purpose of asking questions in the first place is to help your partner access their innate curiosity and intelligence in resolving their own problems. Instead of giving advice or proposing solutions, which always encounters resistance, you invite them to tell the truth to themselves about the situation they’re facing. Once they’re able to do so in a spirit of generosity and self-love, the path forward usually becomes easily illuminated. And they’re able to walk it because the answer came from themselves, and strengthened their own agency, instead of arriving from an external source. I learned another lesson about vulnerability through this exercise: it takes vulnerability even just to ask the question that pierces the heart of the matter.

They might react badly. They might think you’re being nosy or insensitive. They could very well tell you something that is hard to handle. But this vulnerability is essential to the art of asking questions. Unless you’re in the maelstrom with them, feeling the same fear and uncertainty, asking questions amounts to nothing more than an interrogation. Only a question asked with vulnerability can evoke a vulnerable answer.

Impartiality: taking as a starting point that the person in front of you is already perfect in every way The second element in the VIEW is I for Impartiality. Instead of leading the conversation to a predetermined outcome of your own choosing, you hold no preference for where it ends up. Instead of being attached to a goal, outcome, breakthrough, or resolution for this person and their problem, you allow them to lead the conversation where it needs to go. When we talk with people who are dealing with challenging circumstances, we often think we know what’s right for them: take this course, try this product, implement this method, choose this option. We’re uncomfortable just being with their pain. We’re scared to hear what it’s really like for them, and to have to carry that weight. So we hear one thing that kind of reminds us of one thing that worked that one time and…poof, we offer some advice. But the arrogance of believing that we know what’s right for someone after 15 minutes of conversation is staggering. Impartiality invites you to consider that they are the genius of their own life. They know what’s best for them – the best you can hope for is to reflect some of that wisdom back to them, providing access to the truths they already know. This guidance was, of course, the hardest one for me to truly swallow. Joe sat next to me in my partner conversations, calling out “partial!” every time I asked a question that was stealthily leading my partner in a certain direction. Me: “How do you think it makes people feel when you do that?” Joe: “Partial” Me, trying again impartially: “How do you feel when that happens?” Me: “Why do you want to sell your business?” Joe: “Partial” Me, trying again impartially: “What benefits do you think selling your business will bring you?” Me: “Do you value integrity?”

Joe: “Partial!” Me, trying again impartially: “How could you have integrity in this situation?” It took quite some time for me to wrap my head around what true impartiality looks like. It represents a radical level of open-mindedness, an open-ended exploration leaving all my own opinions and judgments aside. It is so difficult, when hearing about a problem that I am certain I know how to solve, to instead ask “What benefit would that bring you?” or “How do you see that action relating to the situation you’re facing?” But the more I do it, the more I am shocked by how different other people’s thinking is from my own. The more I hear about what motivates or interests others about a given path of action, the less I recommend my own solutions. I’ve come to understand that the answers I’ve found only apply to a narrow slice of life, for a narrow slice of the population. Joe explained that, when we are afraid and our amygdala is engaged, we tend to look at things as black or white. Our only options seem to lie at the extremes: break up or stay together; sell the business or keep it; take the job or don’t; move to a new city or stay put. But this is rarely the best way to look at things, because it conceals a vast spectrum of options in between. There are always degrees of freedom, hidden alternatives, and subtle options available. But it is difficult to even see them when acting from a place of panic and fear.

The fear of being alone It was toward the end of day 1 that I had my first major breakthrough. As usual, it came from the most unexpected direction. Skirting the edges of my comfort zone, I came face to face with the fear of being alone. The first few years of my business had been some of the loneliest of my life, toiling for month after month on my computer trying to make something happen, trying to keep my momentum and my spirits high. I’ve thankfully moved on from that time, but had never realized that that experience had left a wound. I had decided at some point that I was never going to experience that kind of loneliness ever again. Fast forward to 2018, and it would seem that my current situation couldn’t be further from loneliness. I am working with 7 close collaborators on a range of interesting projects. I have a support team helping me with bookkeeping, tax

preparation, legal services, and marketing. I have a strong network of customers and advocates constantly telling me how much they appreciate me and my work. But the numbers tell a different story. After peaking in February with the relaunch of my online course, revenue had been falling month after month. Expenses rose steadily as I hired more people on more projects. I spent money as fast as I could to “buy growth,” yet found that none of our offerings scaled as quickly as we needed to cover expenses. I began to tell the truth to myself on day 1 of Tide Turners: that I was so afraid of being alone again, that I was making business decisions with the goal of keeping people around. But I didn’t know how to manage so many people, or make a business of that size profitable. The only thing I knew how to do was hunker down and produce things. So I ignored the emails and phone calls from my team asking for direction, and instead powered through a string of solo achievements, trying to show that I was making something happen. The irony is that this whole situation gave me the very isolation I was so desperate to avoid in the first place. I was sacrificing my business to create a sense of belonging. Yet without a profitable business, there was no team to belong to.

Empathy: allowing their experience in, without falling into it On day 2 we began exploring E for Empathy. It was like wading through a soup of existing preconceptions and associations around this most overused word. For the fourth exercise, we began exploring our relationship to the voice in our own heads. It turns out that this is where empathy has to begin – with ourselves. It is impossible to have real empathy for others unless we first have empathy for ourselves. Each partner was instructed to vocalize their inner dialogue out loud to their partner, unleashing the torrent of doubts, worries, fears, speculations, and musings we usually keep to ourselves. This part was easy. The second part of the exercise was harder: we had to turn on a dime and tell our partner our gifts. It was like a locomotive screeching to a halt, the judgmental mind suddenly reversing course to become an appreciative mind. I noticed how much more difficult it was to see the good in myself, to look inside and find something to praise. I’m always on the lookout for a problem to solve, and will find one on the inside if I need to. We began to ask ourselves, “What evidence do we have that the voice in our heads helps us?” It’s an intriguing question considering how much we revere the advice it gives us. The voice is so often speaking from the neediest, most fearful, most lonely parts of us. As Joe says, “The voice in your head is the unloved bits of previous generations.” Throughout the weekend, Joe conducted “interviews” to help us better understand each letter in the VIEW framework. He would sit face to face with a participant, as the rest of the group sat on the floor and observed. He demonstrated the How/What question-asking, keeping his interviewee in “the VIEW” of vulnerability, impartiality, empathy, and wonder. The most fascinating thing was that each person’s situation was completely different, yet the same process of asking questions always managed to lead them to a place of authenticity and healing. One particular interview showed us the tremendous power of curious questions.

A woman recalled the memories of a traumatic early experience that had led her to a series of disappointing romantic relationships, in which she couldn’t bring herself to open up to her partner. Within 10 minutes of gentle, curious questions, Joe was holding two thick cushions in front of him, and she was taking out her bottled rage in a ferocious barrage of kicks, punches, and screams. When she was finally spent, she sat down with a satisfied “thank you.” Joe explained why having access to all one’s emotions is so critical: “Joy is the matriarch of all emotions – she won’t enter a house where her children are not welcome.” In other words, if you cut off access to any emotion – fear, disappointment, love, anger – you also lose joy in the process. This is most evident when it comes to anger, the most taboo of all emotions in modern society. We learn ways of shutting down our anger at a very young age, because the consequences for letting it out are so severe. But anger, Joe told us, is a form of surrender. Without it, all our other emotions are throttled. Anger is like a hose running through us from top to bottom. If it gets kinked one way, we get an explosive temper. If it’s kinked another way, we get passive aggression. But if it becomes unkinked, you get pure determination, the kind that Martin Luther King Jr. and Gandhi had.

Wonder: leaving the door open to the possibility that anything could happen As we began the interviews ourselves, my newly trained partner began asking me a series of questions about my work and my life, for example: “What is the biggest barrier to your freedom?” “How would you frame the problem?” “What excites you about that prospect?” “How could you have both?” “What does success look like for you?” “What are you afraid might happen?” “What would life look like if that intention was fulfilled?” “What hasn’t been working for you?” “How would you approach that if money wasn’t an issue?” “What would your business look like if it was thriving?” And a cascade of insights began: I realized that I felt an immense obligation to fulfill my potential. As a heavy burden, not an inspiring calling. I felt that I had to repay an enormous debt that I felt I owed everyone who had ever invested in me. I broke down in tears as I thought about generations of my ancestors, who had sacrificed and struggled so that I could have a better life. I thought of my parents and grandparents, who had spent so many years teaching me everything they knew. I thought of the countless teachers, coaches, mentors, managers, friends, and romantic partners it had taken to make me the person I am today.

I had never realized what a crushing burden I felt at the impossibility of ever paying back the love and care that all these people had given me. My source of motivation for many years had been the desire to pay off the debts of my privilege. That fuel had served me well, but I saw that it had finally exhausted itself. I had exhausted myself. I was done with the endless task of proving that I was good enough, capable enough, successful enough to deserve what I had been given. As I talked through these realizations with the group, Joe looked at me and asked, “What is a different interpretation for all that?” I responded almost instantly: “That they chose to sacrifice because they loved me, and all they ever wanted was for me to be free.” I didn’t need to pay anything back. I didn’t need to prove that I deserved the privilege I had. It is a privilege to do meaningful work that has a positive impact on people’s lives. But I have the privilege of doing that work out of gratitude and joy, not out of obligation. As the burden of obligation lifted from my shoulders, I had a ground shaking breakthrough: I had no desire to build a large business. This thought stopped me dead in my tracks. It was the unthinkable thought I hadn’t allowed myself to consider. I had been working for years with the unstated assumption that I had to build the biggest possible business as fast as possible. I leapt at every opportunity to grow or gain exposure, even if it made me miserable. I spent lavishly on anything that would help me go bigger or move faster. I took on projects or clients out of obligation, as if I had no choice in the matter. Perhaps influenced by the tech startups I was surrounded with in Silicon Valley, I thought hypergrowth was the only path forward. The outcome was that I had an unprofitable company bleeding cash, a team I didn’t know how to put to use effectively, a range of projects and responsibilities I had no desire to pursue, and no time left over for the open-ended thinking and writing I loved so much. Pushing hard against what reality was trying to tell me, I found reality pushed back even harder. When I really got to the bottom of what I wanted, digging down beneath layers of “shoulds” and “ought tos,” I found that what I really desired were very simple things: more time with my family, a small circle of smart friends and collaborators, time to think and travel and explore new things, interesting projects that made a real difference, health and peace of mind. I’d placed all

these things on the far side of building a massive company, telling myself I couldn’t indulge until I’d done it. But what my partner’s questions revealed is that they had always been there for the taking. Wonder is the final element in the VIEW framework, and the most mysterious. It asks us to question whether we know where all this is going. It asks us to stand in awe of the complexity and ineffability of the human experience. It has the questioner not try to find a problem and solve it, but to always remain curious as to how the human being in front of them works, and why. Remaining within the VIEW is really just a checklist for unconditional love. You can cycle through each element as you are asking questions, asking yourself which one is missing, which one you’re withholding. Vulnerability asks you to constantly turn toward what you’re protecting, what keeps you separated, and have the courage to question it. Impartiality has you take as a starting point that the person in front of you is already perfect in every way. Empathy has you allow their experience in, without falling into it. And Wonder leaves the door open to the possibility that many things can happen not covered in any framework or checklist.

Aftermath On Sunday evening we walked back out into the world, charged with the homework of using our new question-asking powers and VIEW framework to produce new connection and intimacy in the relationships that matter most to us. It’s easy to undergo a unique experience like this one, and to walk right back into the same patterns and habits that had you dissatisfied in the first place. It is the practice that makes the difference. New practices take practice. I’ve waited a few months since completing the Tide Turners workshop before writing this account. I wanted to see if I would be able to put these breakthroughs to use in the “real world.” I’ve found that they are incredibly effective in a wide range of situations. I’ve used the tools I learned there to help a friend see that his career was a completely wrong fit for him, and to begin the transition to something else. I’ve used them in my coaching, helping my clients to see the deeper layers of narratives driving their “bad” habits (and even questioning the labels of “good” and “bad” that keep those habits locked in place). I’ve used it with my family members, facilitating incredible breakthroughs in their relationships and careers. And I’ve used it on myself, bringing curiosity to situations that before I would have felt only self-criticism. The VIEW and How/What questions have been among the simplest and most effective coaching tools I’ve encountered. I believe that Tide Turners is part of a new generation of personal development programs, adapting to modern ways of communicating and relating while also addressing some of the traditional pitfalls of the self-help industry. The self-help industry often treats the mind and body as enemies to be beaten into submission. Instead of adding yet another strategy or technique, burying your true self under yet another layer of obligation, this new generation focuses instead on unwinding the negative patterns that keep us from accepting and loving ourselves. Joe said something that has really stuck with me, and that I’m only just beginning to understand: that you have to allow your heart to break a little to increase your capacity to love. I interpret this to mean that it is only when we expose our hearts enough to allow them to be broken, that we have a chance to

expand our heart’s capacity. And it is our heart’s capacity, not our intellectual capacity, that is the bottleneck to the change we want to see in ourselves and the world. I went into the workshop seeking to grow my self, my business, and my work. For myself, I discovered that my growth edge is my heart – connecting to my desires, my dreams, my emotions, and my body and aligning all of them with what I do every day. For my business, the growth edge is fundamentals. Profitability, financial solvency, systems and routines needed to even out fluctuations in revenue and help me make better decisions. I’m starting to budget seriously for the first time, and use basic financial metrics to make decisions, instead of purely by intuition. And for my work, I think the growth edge is to give it away. I’ve been at the center of everything, the source of everything for long enough. In writing the Building a Second Brain book, my intention is to write simply and clearly enough that anyone can benefit from it. This is some of the hardest writing, to separate out my ego and my point of view from the essential methods that just work. It is only by surrendering control of what these ideas could become that they have a chance of growing beyond my reach. You can sign up for VIEW’s newsletter at the bottom of this page to receive updates on future courses. Or follow Joe on his Facebook page, where he posts short videos.

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A Productivity Expert’s Guide to Working with a Virtual Assistant Over the past five months I’ve worked closely with a virtual assistant (VA). This article summarizes what I’ve learned about the best ways to handle the working relationship, in the form of a guide for anyone who wants to do the same. Hiring a VA can be an absolute game-changer for your productivity, effectiveness, and peace of mind. As important as it is to optimize your own time and effort, there is huge potential upside in bringing on a real human, with all their own abilities and knowledge. But I say “can be” because it depends a lot on how you set goals, expectations, and policies. In this guide I’ll give you my recommendations for how to do so, along with numerous examples and templates you can use for yourself.

Hiring a VA For your first VA, I highly recommend working with a matching service. They provide: Vetting and initial screening interviews A matching that takes into account your needs The option to require certain qualifications, and your choice of time zone In some cases, an onboarding and training process for their VAs with best practices on communication, time management, and common productivity tools The bottom line is, VA matching services take care of much of the administration and logistics required to work effectively with a VA, so you can get the most value for your money. For your first time, it is well worth having all this support to make sure everything runs smoothly.

Cost My general recommendation is to pay at the high end of the scale. This means between $20-$25 USD per hour. You can easily find a VA in Asia or Eastern Europe for a few dollars an hour, but you’re always going to have to be double checking their writing, correcting their mistakes, and second-guessing whether you can trust them with a project. By paying at the high end of the scale, you’ll get someone with significant administrative experience, who speaks English good, and who is somewhat familiar with U.S. and international business culture. You don’t realize how many unstated expectations and norms there are until you work with someone who doesn’t know them. I highly recommend hiring someone with a commitment of at least 20 hours per week. That might seem like a lot right off the bat, but it will ensure that both of you are committed to getting past the challenging training period. This also

makes it feasible for you to be their only client, which I think is ideal. This means you are looking at a financial commitment of at least $400 per week, or $1,600 per month (20 hours per week times $20 per hour). In other words, this is a major expense. Don’t take it lightly, because you really are hiring a human to invest a huge amount of their time and energy into your work or business. You will also be investing an extraordinary amount of not only money, but more importantly, time, trust, and energy in someone you will likely never meet in person. It’s worth doing it well.

Automatic Billing My strongest recommendation, regardless of which route you choose, is to set up automatic, fixed-price billing. You should be automatically charged the same amount every 2-4 weeks, even if your VA doesn’t have enough work to fill those hours. Automatic billing creates a pressure on you as the client to constantly be giving your VA things to do. This is essential, because for the first few months it will take you much longer to package up and explain a task than to just do it yourself. This creates a powerful disincentive to assigning tasks to your VA, especially when you can “save money” by giving them less to do in a given week. The best way to balance this with an equally powerful incentive is to know that you’re paying them whether they have anything to do or not. As an entrepreneur or freelancer, the idea of paying someone to sit around is maddening. This will convince you to invest the time to assign tasks to your VA, which eventually will pay off as they learn your habits and projects.

Best practices for working with a VA Here are my recommendations for how to work effectively with a VA over the long term, from most to least important.

Maintain a standing weekly call I strongly recommend maintaining a recurring weekly check-in. So much can happen in a week, it’s important to get on the same page even if you think all the needed tasks are totally clear. And I recommend doing this as a video call whenever possible, because a lot can be conveyed with body language. I use the Zoom video-conference app, and turn on automatic recording for every call:

11: You can find this setting by logging into your Zoom account, clicking “My meeting settings” in the left sidebar, and clicking the “Recording” tab

I set the default recording location to a folder on my computer that automatically syncs to Google Drive (using the Backup and Sync tool). This folder is shared with my VA, which means that she has access to the video recording within 2030 minutes of the end of a call, with no additional action required on my end. These weekly calls generally take 20-30 minutes, but I schedule it for an hour in case something more complex comes up. I usually spend the 5-10 minutes before the call looking over the agenda and thinking of any questions or new tasks. For the first few months, I recommend using the full hour to review several SOPs (standard operating procedures) each week.

Maintain a standing agenda What do you do during this weekly standing call? You go over your standing agenda, which I keep in a Google doc, which is saved in my bookmarks bar.

12: Screenshot of my standing agenda I use with my virtual assistant

Click here to see my actual standing agenda for the last 5 months, with only last names, passwords, and some links redacted. This document serves many functions. Throughout the week, we both jot down questions, ideas, clarifications, requests, etc. to form an agenda for our next meeting. During our meetings, both of us have this document open and take notes on everything we discuss. Our agenda turns into meeting notes, which we can both refer to retrospectively if we need to. The structure of this document is very simple. Each meeting has its own heading, which is the date. The bullet points below the heading contain the main points covered in the meeting. We try to summarize any next steps at the end of the outline, for quick reference during the following meetings. But since this document is only used by two people, you can keep it pretty informal.

Set up a shared password manager The most useful tool when working with a VA is a shared password manager. I use and recommend 1Password, but I’ve also heard that LastPass works well.

These apps allow you to set long, difficult-to-guess passwords for your online accounts, which is a very good idea security-wise, but then have a centralized app that “remembers” them for you. You “unlock” this app using a single master password, and then the app fills in the password for a specific site for you.

13: The 1Password interface on Mac

I currently have 170 logins stored in the app, which I’d say is about average for anyone who spends a lot of time online. I use the “Team” plan, which costs $3.99 per user per month. This comes out to $8 per month for the two of us, or $96 per year. This is a steal considering that this app protects your online security and privacy. 1Password allows you to keep separate “vaults” depending on what you want to share. I keep logins that I want my VA to have access to in the “Shared” vault, which includes my airline and travel accounts, business social media, Squarespace, Eventbrite, WordPress, UPS and Fedex, Typeform, and Splitwise. In my “Private” vault I keep more sensitive accounts, such as my online banking, personal social media, Google, Apple, Amazon, Godaddy, and Paypal.

14: Screenshot of the main vaults I use to delegate logins to my VA

It is very easy to move logins from Private to Shared, as your VA needs access to new accounts and your trust in them increases. I’ve done this on my mobile device while on a layover at an airport, which is very convenient. You can also easily revoke access at any time if you need to. Before sharing your own login details, check to see if you can create a separate user account for your VA. This is a better option for security, and allows them to manage their own settings and notifications. Often this requires upgrading to a paid plan, however, in which case I’ll usually share my own login. See this article for a full description of the different apps and services I use. Password managers can also be used to store other kinds of sensitive data, such

as passports, other identity documents, credit cards, software licenses, and direct deposit and tax information. All these items can be shared with your VA as needed.

15: Categories of items you can save in a password manager such as 1Password or LastPass

Eventually, you can turn over management of the password manager to your VA, so he or she can share and revoke access for others on your team. 1Password has sophisticated permissions levels that are easy to change.

Schedule intro calls with each person on your team It’s really important to think of your VA as a full-fledged member of your core team. Just because they work remotely, work only part-time, and you’ve never met them in person, doesn’t mean they are any less important to your work. As your right hand, they need to have your full trust and authority in everything they do.

For that reason, I recommend asking your VA to schedule 1-on-1 calls with the main people you work with, whether they are employees or contractors. Have them get to know each other, including their responsibilities and projects.

Set up a calendar of recurring tasks to be performed One of the most useful responsibilities to give your VA is recurring tasks that need to be performed on a regular basis, but don’t necessarily take a lot of time or creativity. This could include: Maintaining a shared team calendar (to keep track of deadlines, payable dates, major events, vacations and time off, etc.) Scheduling calls (including finding the best time, communicating it to everyone, and sending out the link) Responding to customer service emails (including answering basic questions, pointing out helpful resources, and issuing refunds) Monitoring and responding to routine emails Promoting blog posts and other things through social media Checking in with accounts receivables (i.e. people who owe you money) I recommend putting all these items on an online calendar that is shared between you, and potentially shared with your team as well. That way everyone can see what the VA is taking care of and what’s coming up soon.

Record short “how to” videos Instead of writing out long explanations via email for how to do things, which is time-consuming and error prone, a very effective way of training a VA is to record short “how to” videos. This can be done with Quicktime on a Mac (File > New Screen Recording) and I’m sure there’s an equivalent on Windows. Hit record, and then narrate your way through a task that you’d like your VA to

perform. I used this approach to demonstrate how I work my way through my email inbox. My VA watched this recording, and sent me back this “email protocol checklist” that summarized my rules of thumb: Goal: Emails with predetermined outcomes will be taken care of by Kathryn. Tiago can come to his inbox and know that each email is substantive. 1. Start with oldest emails first 2. Sort emails accordingly: a. Updates Tab: i. Starbucks, auto glass, unbounce etc. ii. Sale confirmations iii. Promotional Offers iv. Go Daddy renewals v. Weekly digest vi. Medium updates vii. Most receipts viii. Memberful new order notifications ix. Comments on photos notifications x. Emails about apps being connected to each other. xi. MailChimp notifications xii. Surveys (archive after moving to updates) b. Primary Tab: i. Updates to Google Doc notifications ii. Travel information (as long as it hasn’t passed). 1. i.e.- Jet Blue, Expedia etc. iii. Forum messages iv. Uncompleted drafts

v. Teachable notifications vi. PayPal notifications vii. Email exchanges viii. Tim Ferriss blog posts ix. Squarespace 3. Add applicable items to Instapaper: a. RibbonFarm b. Breaking Smart 4. Archive emails if: a. The event is over. b. Tiago no longer needs to see it. c. A back and forth dialog is completed and requires no further follow-up. 5. Unsubscribe from emails if: a. They are ads that don’t look applicable to Tiago. 6. Notify Tiago of any time sensitive emails that may require his immediate response. Helpful Tips: Archive using Keyboard shortcuts (turn on in Gmail settings). Download Instapaper toolbar to add items with one click. I would have had difficulty coming up with this checklist myself, because these rules are so ingrained for me. I’ve effectively outsourced the process of creating a process around my email, which will make it easier for my VA to manage my email, easier for me to see what she’s done, and easier for a future VA to pick it up if needed.

Examples of good projects My top guideline for projects is: assign a diverse mix of administrative projects, long-term projects, and learning projects. This ensures that the work is interesting, gives them opportunities to learn new skills, and gives them flexibility to match any block of time they have available with an appropriate task. Also, there will be periods when one kind of project runs dry. Having a diverse mix gives them something to switch to if you don’t have an immediate need.

Administrative projects These include relatively straightforward projects you would normally associate with a personal assistant. Early in your relationship, these will be the great majority, and you’ll have more of the other two over time. Examples of admin projects that I’ve had my VA complete for me: Research overseas cell phone options and visa requirements and send me a summary Collect all replies to an email and send each of them a slide deck Make a transcript of a video call with a client Onboard and offboard other staff members (and create a checklist for how to do this in the future) Summarize a tweetstorm thread in a Google Doc Change of address for all online accounts Apply for vendor status for a client Create drafts of Mailchimp mass emails

Mock up new webpages Make a Facebook group or event page Research hotel options for wedding Create and update wedding website and invitations Fixing small billing and technical issues Changing voter registration after a move Research new online services to see if they’re a good fit for us Create a coupon code for an online course and send it to a marketing partner with instructions on how to access it Summarize the key takeaways and next actions from a meeting and send to all the attendees

Learning projects These include researching new topics or learning new skills, even if they don’t result in an immediate deliverable. For example, I paid my VA to take my productivity courses a little bit at a time. This gave her new capabilities that I knew we would both benefit from, and helped us synchronize the way we worked. Examples of learning projects that I’ve had my VA complete: Take my Get Stuff Done Like a Boss course and set up a task manager Take my Building a Second Brain course and set up a knowledge management system Read my series on Progressive Summarization to be able to summarize sources for me

Long-term projects These include projects that aren’t high priority or urgent, but you know you’ll need to have completed eventually. Examples of long-term projects that I’ve had my VA complete for me: Set up Amazon Affiliate accounts and replace all product links on blog with affiliate links Research requirements and apply for Amazon Influencers program Make a list of possible speaking engagements and remind me when application deadlines are approaching Keep a list of everyone who commented on a Google Doc draft of my book, so I can include them in the Acknowledgments section Updating my links and bio on various sites (such as Amazon Kindle and Goodreads)

Other lessons learned Train them using my courses I found that my three self-paced online courses on digital productivity were the perfect way to “train” a VA. They will learn not only how to use a bunch of productivity apps, but how to use them effectively, in line with proven practices. Here are the key skills you should have them focus on from each course: Get Stuff Done Like a Boss will lead them through setting up a task manager where they can manage all the open loops you will be sending their way. They should focus on: Defining their tasks in terms of clear “next actions” Taking a moment to identify their desired outcome before starting on a task Organizing their tasks by project and area of responsibility Reviewing and reflecting on their open loops and responsibilities on a regular basis Executing their tasks according to whichever context they find themselves in Design Your Habits will teach them how to establish and stick to productive routines. This is especially important when they are working remotely, without supervision, and have to manage their own time and energy. They should focus on: How to identify high-leverage keystone habits for maximum impact Science-based techniques for anchoring new habits in existing routines

How to build self-confidence and momentum using small wins How to modify their environment to support habit change Improved self-understanding and self-confidence through guided exercises And finally, Building a Second Brain gives them a proven, repeatable process for managing all the knowledge they need to do their job. They should focus on learning how to: Capture small bits of valuable knowledge that are surfaced during their work Document frequent tasks and processes in a checklist format in digital notes Organize all the files they will need to create and manage in a simple, yet highly actionable system (using my PARA organizational method) Summarize documents and notes in a condensed format while preserving the context it was found in (using a technique called Progressive Summarization) Create new documents, checklists, spreadsheets, and webpages using the content they’ve collected As strongly as I recommend notes apps for everyone, I especially recommend them for working with VAs. It is very overwhelming to onboard someone by sharing your entire file system with them all at once, and expecting them to know where to find things. With a notes app (especially one organized using my PARA method), you can

share one note at a time with them, only if and when they need it. Then as they join each new project, you can share only the notes related to that project. And only when they take on ongoing responsibilities, you can share the notes related to an area. By introducing a VA to your “knowledge base” slowly over time, you give them the opportunity to build up the context that’s necessary to understand it all. This not only keeps them from getting overwhelmed, it gives them the confidence and ownership to begin contributing to and managing this precious knowledge.

Make a project wish list Early on in your work together, I recommend creating a “Project Wish List” of projects you would love your VA to eventually take on. Maybe they are projects that you never have time for, things you’ve dreamed of for a long time, or projects that only make sense if the right opportunity comes along. These are your “someday/maybe” projects. This wish list gives your VA something to aspire to. They can keep this list in the back of their mind as they execute more urgent projects. If the right opportunity presents itself, they already know you have a project in mind, and they can raise it with you to get the green light.

BCC them on everything Even if you give your VA direct access to your email account (which is very easy using Gmail), I still recommend BCCing them on almost every email you send. Most things they won’t need to answer, but the more background context they can gather, the better their ability to notice when something is going off the rails. If you CC them, you also give the person you’re emailing the option to email your VA with follow-up questions, instead of you.

Your VA is a reflection of you Some people seem to hire VAs as a way to “get organized.” I think this can work, but not in the way they expect. If you think your VA is going to whip you into shape and corral your chaotic digital life into order, you’re mistaken. That’s because the way a VA works is always a reflection of you. They will be disorganized in the same ways that you are disorganized. They will lack clarity in the same places you lack clarity.

Where a VA can help is as a form of accountability. Knowing that you are paying someone and that they can only be as productive as you enable them to be, you can use that as an excuse to do the organizing you already know you need to do. For example, bringing on a VA got me to finally convert my shared team Google Drive, which I’d always kept messy, to my PARA system. The messy approach worked for me, but I knew would be terribly confusing for her.

The value of a second pair of eyes A lot of the value of a VA can’t be precisely quantified. It is the value of a “second pair of eyes.” Many of us work for ourselves, on our own, or remotely, which means that problems and mistakes can spiral out of control before we notice them. Having someone in the background looking at your emails, checking the calendar, and monitoring deadlines provides a layer of security and peace of mind that is hard to put a price tag on. For example, in helping manage my email account, we found that most emails that make it through all the filters need to be handled by me in some way. They just require too much background context to act on. But knowing that I had someone monitoring for any emergency often gave me the confidence to spend a few more hours on a project, without constantly checking my email for anything blowing up. It is in these extra hours of focus that breakthroughs often happen. It is with this extra layer of confidence that you can take a few more risks, try something new, or just feel okay taking the rest of the day off. And that is priceless.

Lessons learned from a VA’s perspective Here is a list of Top 10 Lessons Learned written by my VA, Kathryn: 1. Establish the preferred method of communication right away. Everyone has a way they prefer to communicate. Whether this is via phone, text, email or other app such as Slack, determine upfront what your client prefers. This will ensure you’re both on the same page with clear expectations. 2. Be patient in the onboarding process. Give yourself at least 30 days to learn the ins and outs of everything. This can include the client’s personality, the company culture, new software and apps you’re using etc. Don’t be afraid to ask questions during the onboarding process. The first 30 days are all about getting acquainted and building trust. 3. Set measurable goals up front. Working with a matching service, this is something they’re really big on. When starting with a new client, we set 3 Wins and 3 Goals based on their needs. This gives you some benchmarks to reference to make sure you’re staying on the right track. 4. Be on time for meetings (even virtual ones). For me, this meant logging onto the call 10-15 minutes early. You never know what internet or computer issues you’re going to run into and this gives you time to troubleshoot in the event something goes wrong. On that note, invest in a hotspot for rare emergencies where WiFi isn’t available. 5. Schedule a regular meeting time with your client. We opted to meet once a week via Zoom call. We used our Standing Agenda to guide our conversation and took the opportunity to catch up on anything that was more easily discussed “face to face.” I highly recommend recording these calls as they are helpful to reference if you missed any details. 6. Be open to trying new things. I came into my new job with Tiago expecting to make suggestions on ways to improve efficiency and make his job easier. By nature of what he does for a living, I quickly realized I was going to learn equally as much, if not more! It was a huge stretch for me at first, but as I embraced it I gained new tools that will last me a lifetime. 7. Create a project list. Whether you use a simple Google Doc, or a more robust program like Asana, create a project list that you and your client both have

access to. This helps provide accountability for tasks you’ve discussed. Tiago and I used a running Google Doc. Each week I dated it for the day we’d be meeting. He would add things he needed to share with me and vice versa. As I completed tasks, I crossed them off and added any needed notes. 8. Communication is key. As a VA communication is key. Since we don’t have the benefit of being in the same building as our clients (or even the same state for that matter) it’s imperative that you keep open communication with one another. For me, this was sending updates on the status of any projects I was working on. Even if nothing had changed or progressed, I would keep Tiago in the loop. 9. Don’t be afraid to ask for what you need. Just do it nicely. Ultimately my job as a VA is to make Tiago’s life easier so he can focus on the things only he can do. So once he’s delegated something to me, he may not be thinking about it any longer. If there is a piece of information I need in order to complete something, I reach out. Depending on his schedule, he may not respond right away. Depending on the time sensitivity of the task, I may reach out again the same day, or wait a few. The important thing to remember here is your client has hired you to help them. So don’t be afraid to do just that. 10. Have fun! Get to know your client and enjoy the process of serving them.

Live conversation and interview Watch this video for a 45-minute conversation between Kathryn and I about what we learned by working together, including questions from a live audience. Including: Demos of a standing agenda and how we use it Demo of using a text expander (Alfred) to quickly enter common information and standardize how tasks are written How to make weekly meetings fast and effective How Kathryn adjusted to working with a client, including learning new productivity techniques and tools What Kathryn was looking for and what had her seek a VA position What the application, evaluation, and selection was like to become a VA What kinds of support VAs receive as part of their contract Our recommendations for how to handle communications, managing expectations, and setting goals How to take on the “manager’s mindset” as an entrepreneur, solopreneur, or freelancer

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About the Author Tiago Forte is a writer, speaker, teacher, and researcher exploring human potential and the future of work. In a previous life, he worked in microfinance, served in the Peace Corps, and consulted for large companies on product development. Tiago runs Forte Labs, an education company dedicated to helping knowledge workers transform their productivity using technology. Past clients include Genentech, Toyota, Nestle, and the Inter-American Development Bank, as well as startups, incubators, universities, and nonprofits around the world. Tiago writes for and manages the Praxis blog, where he writes about topics relevant to personal productivity and effectiveness, including the future of work, workflow design, behavior change, design thinking, and personal knowledge management. His work has been featured in The New York Times, Inc. Magazine, Harvard Business Review, The Atlantic, and Lifehacker, among others. Get in touch at [email protected].

About Praxis Praxis is a subscription-based blog dedicated to exploring and creating the future of work. Written and curated by Tiago Forte, its mission is to provide a private forum for smart people to learn about and discuss some of the most insightful productivity ideas, frameworks, and practical methods in the world today, as well as how to implement them. For $10 per month (or $100 per year), members get access to: 1–3 exclusive articles per month, written or curated by Tiago Members-only comments and responses Early access to new online courses, ebooks, and events Topics we will explore include: Workflow design and Getting Things Done Habit formation and behavior change Futurism and science-fiction prototyping Design thinking and design principles for productivity Self-tracking and data analysis Organizational design and culture Creativity and emergence Theory of Constraints and applications to knowledge work Mindfulness, alternative states of mind, and the inner game Knowledge management and extended cognition and many more to come… I know the time you have to invest in improving your productivity is limited, and my goal is to help dramatically increase the signal-to-noise ratio of the information you consume. My role will be to provide seeds of insight —thought pieces, implementation guides, interviews, case studies, experiments, audio and video, guest articles— to help spark powerful conversations. I believe that human productivity is fundamentally unbounded, that it doesn’t require sacrificing health and happiness, and that work can be a vehicle for personal growth and self-expression. If you believe the same, and are tired of the same productivity advice endlessly recycled, join me below. Click here for more information, and to become a member. Email questions to [email protected].