$100,000 friends

Recently over dinner with new friends I asked, “How much would you pay to have your best friend live on your street? Wherever you move poof they’re your neighbor and they’ll never know you paid.” After a moment of thought, the couple independently arrived at the same number: $100,000 each.

By this point in the conversation I knew that they had normal enough jobs, and it was reasonably safe to assume their combined after-tax income was also right around $100,000. I did some back of the napkin math and it turns out what they were suggesting was: “Outside of basic sustenance we’d pay every single dollar each of us makes for doing 16,000 total hours worth of work over the next four years to have our two best friends live within walking distance.”1

Were they just bad at theoretical scenarios? Were they insane? I tried to find out. Over the next several months, I asked the same question to fifty people. About thirty of them said $100,000. Ten of them offered more. Two said $1 million. Three said, “50% of my net worth.”

Before I began asking others this question, I’d asked myself, and the number I wrote down in my journal was: $100,000. Below it, “Ideally in installments. I’d pay more if I could.” This turned out to be the going rate, but really it was symbolic. Shorthand for an uncomfortably high, round number, meant to flirt with the absurd and clearly suggest: a lot, like a lot.

The question also animated people with excitement. It typically led to wild stories, cherished qualities, and qualifying explanations about the particular greatness of certain best friends. It’s the kind of thought experiment that makes you feel things, but unfortunately it remains theoretical. There’s usually a legitimate reason why we can’t move, or they can’t move. Sometimes it’s work, sometimes it’s family. Some people have multiple best friends from different stages of life in different cities. There are innumerable plausible reasons, and sometimes they’re not specific. A word I heard a lot was: “impossible.”

Indeed, it may be impossible or impractical, but as soon as you’ve asked yourself this theoretical question, priced things out, and eyeballed an eye-watering number—there are two things you can and should do. First: you should plan a non-negotiable recurring trip with the best friend(s) you have in mind. And second: you should take dramatic action to find more people like them where you currently live. In other words: you should find new best friends locally. Not normal friends, best friends.

I won’t explain how to plan a trip with your current best friends, I’ll only reiterate that you should and that it should be a regular thing. There is no substitute for weekly in-person contact with your closest friends, but the next best thing you can do is invest in semi-regular experiences together. Even at great expense or inconvenience.

The question of finding new best friends at a new stage of life in a new place is more fraught and controversial. Is it even possible? I think so. For starters, it helps to consider what answers like “$100,000” reveal about the nature of friendship.

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The power law of friendship

The answers to my theoretical question revealed an under-appreciated consensus: there’s a power law to friendship, and the rare-air of best friendship is worth more than all the others combined. If you’ve lived a chapter of life alongside your best friend, then you know that there’s nothing that makes you feel more alive or more yourself than highly regular time spent doing things together. Nothing creates more Technicolor memories per unit of time. Nothing compares to the rhythm of life, to the belly laughs, to the depth, to the love, to the mischief, to the mutual understanding, to the feeling of being understood across multiple contexts. Aside from a romantic life partner, it’s incomparable. At peak moments, during peak memories, it feels like the whole point of life itself.

With this in mind, the same reflexive logic unfolds in everyone who is pressed to put a price on living near their best friend. They confront the value of friendship in monetary terms, they understand that money buys things, and they simply can’t think of anything remotely close to the value of a best friend.2

So they say “$100,000” with a straight face. And the number typically increases when you press them.3

Money is time

Everyone recognizes the value of a best friend emotionally, and most people are capable of putting a kind of price on it theoretically, but the crucial missing link between a theoretical thought experiment and a galvanizing wake up call is the translation of money into time. Since “$100,000” is just another way of saying: “I’d pay a lot of a thing I traded a bunch of my time for in the past”—an equal substitute would be to carve out an equivalent amount of future time, and spend it searching for a new best friend nearby. Could you find a best friend if you were fully committed to the problem and you gave yourself 1,000 hours to solve it? That’s roughly five hours per week of friend-finding-effort for the next four years.4 Feels like a slam dunk to me.

But this is where my thought experiment runs into the most pushback. Most people don’t believe they could proactively go out and find a new best friend for two reasons: first, they believe there is an irreplaceable ‘specialness’ to best friendship that derives from shared life experiences during formative stages of life; and second, they believe it’s hardly even possible to go out and proactively find okay friends, let alone a new best friend.

To the first point, it may be a bit late to make this semantic concession, but I don’t believe in best friendship as a singular title (given only to one person), I believe in it as a friendship tier. It’s the highest bar. I have plenty of friends, but only four people in this tier. I met each of them at different stages of life—some in my childhood, some relatively recently.

One of my best friends, Tim, skyrocketed into the top tier within a matter of weeks, and solidified a permanent place in the category over the course of a year. He is my counterpoint to the idea that best-friendship can’t happen in a new chapter of life, or that it can’t happen quickly. It simply took two people recognizing how much potential there was in the relationship (something that is usually easy to recognize), and going all in. Tim and I spent a ton of time together over the course of a year, but that’s really all it took—densely experiential-time piled on top of extremely high compatibility. You can’t replicate an old friend’s distinct flavor of specialness or a shared history, but you can develop something equally valuable over time with new people in new chapters, which reflect the ways you’ve changed.

To the second point: how do you meet a Tim? This can’t be planned. And this is what people hate. The way Tim came into my life was totally ridiculous: he met my brother lobster diving. But there is a difference between predicting how something very specific will happen, and radically increasing your odds of orchestrating a desired outcome. The way to manifest new, best-friend-caliber relationships is exactly how you solve any big, nebulous problem: you spend a lot of time on it, you design a good plan, you continuously pivot and refine your plan through trial and error, and you don’t stop until you’ve solved your problem. If you spent 1,000 hours looking in earnest for your next Tim, you’d find one.

You’d even find one without employing especially creative solutions—by simply: joining a few clubs, attending interesting events, volunteering somewhere, becoming a regular. Socializing a lot. Saying ‘yes and’ a lot. Accepting and extending invitations. Asking new people to introduce you to their most interesting friends who share your niche interests. It’s not complicated. You simply must be willing to stay at it, even if it takes five hours per week for four years.

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Rejection and awkwardness, a small price to pay

People shudder at friend-finding in general. It’s one of those open-ended problems that even intelligent and highly capable people are selectively agentic about: they complain about how hard it is, without directing legitimate effort or creativity at the problem.5 In reality, the cultural and individual resistance (and the acceptance of loneliness as an alternative) is mostly related to fear of rejection and aversion to awkwardness. It also has a lot to do with avoidance of personal responsibility—without the possibility-rich social environments of our youth (school, team sports, camps, etc.), adults are forced to take responsibility for creating the conditions that will get them what they say they want. And it’s true: there is no ready-made playbook for finding friends, no easy button, no dependable, swipe-able app. Good luck Googling it.

But is it impossible? Of course it isn’t. People have best friends, and they make new ones at all stages of life. The problem is that it’s not pursued as a solvable problem, commensurate with the huge value we place on it, or with the amount of effort and time required to make it inevitable. It’s approached as a thing that happens to you if you’re lucky—not something that you can happen to by making your own luck.

Baked into my original question is an assumption about modern friendship that proved to be categorically true: nobody lives in the same place as their best friends anymore. I never had to qualify the question. People just understood that the premise depended on their best friends living somewhere else, and in basically every case this was true.

So chances are, your best friend lives far away too. If that’s the case, my follow up questions for you are the same non-theoretical ones I found myself asking people who said “$100,000”: What are you doing to make a new best friend where you live now? How much time is the problem worth to you? Do you think you could find a new best friend if you spent 500 hours working hard on it? 1,000 hours? 10,000 hours? Even more?

Wouldn’t it be worth it if you could? What is a better use of time?

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Thanks to Michael Dean for feedback on this piece.

Religious devotion

No pastor or priest has ever said to the congregation: “You already get the Bible. You understand Jesus. We’re moving on to another book.” There is no other book. The Bible is the whole ballgame.

If you’re a devout Christian, this is how the Bible works: you read it, then you read it again and again and again for the rest of your life. You read it verse by verse, until the individual verses illuminate your life with explanatory insight. You layer the parables onto daily decisions, interactions, and experiences like a teleological algorithm. You read the Bible each morning, alongside a devotional or another book that explains the Bible. On Sunday, you learn from a Bible expert. Midweek, you meet for a Bible Study. You sing hymns and pray to the God of the Bible using the language of the Bible. Your leather-bound Bible has gilded pages and your name is embossed on the cover — and when you’re not annotating that Bible, you’re making notes in the Bible App on your phone.

Naturally, the Bible transforms and shapes the lives, identities, and day-to-day decisions of the people who do these things. That’s the whole idea, that believers should “become the word,” should embody the truths and principles of their one Holy Book. There is an obvious lesson here: if you pick one book, surrender to it, and filter your experiences through it, the book will change your life. The kind of devotion described above is so total and singular that it hardly seems sane to apply it to anything outside the realm of religion, and yet there is a whole genre of books that people turn to for many of the same reasons that people turn to the Bible. And it would cause complete life makeovers if readers applied biblical devotion to this genre in a similarly narrow way. The genre is self-help.

Self-help and personal development books are the secular equivalent of the Bible. They represent the second most popular genre of books in the world because they provide the promise and hope of personal transformation.1 Their scope is more limited and less existential than the Bible, but they target our deepest vulnerabilities and intractable personal problems: self-acceptance, wealth accretion, addiction, weight loss, priority management, presence, meaning making, winning friends and influencing people. Self-help books offer instructions for navigating the world and arriving at your desired destination, but for all their popularity, they are largely futile.

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The pseudo-progress death-loop

Generally speaking, there are three reasons self-help books are ineffective. The first, is that many of these books are written by grifters and gurus, and they are packed with unproven claims that aren’t scientifically or even anecdotally supported. The second, is that there is a huge follow through problem: 80% of ‘highly-motivated readers’ don’t even finish the self-help books they set out to read.2 And the third reason is that readers are drowning themselves in self-development content — cycling endlessly through books and podcasts and audiobooks, deeply desiring transformational change, and temporarily satisfying that desire by consuming novel inspiration rather than taking action.

All three of these problems are solved by picking a single credible self-development book by a believable author, and reading it with the kind of biblical devotion described above. This would completely change your life.

The people who are most hell-bent on changing their lives struggle with the third problem. It’s the cultural epidemic that gets no airtime. I call it the pseudo-progress death-loop. This is what it looks like: you read a self-development book and you get excited about the ideas, and you swear you’ll change your habits, change yourself, stick to such-and-such a morning routine, etc. Meanwhile, you listen to The Diary of a CEO on your daily commute and Modern Wisdom while exercising, and you feel the same buzz from the podcast interviews that you feel from the books3 (← important footnote). And in a few weeks, you’ve consumed the equivalent of 10 self-improvement books in the form of dense podcast interviews with topical experts — and you’ve downloaded one of the interviewees books on your Kindle, and you’ve started reading it even though you haven’t finished the book you were buzzing about earlier. The excitement surrounding the transformational insights from one book or interview perpetually gives way to imagined possibilities brought on by the next one.

The pseudo-progress death-loop has a simple neurobiological explanation: the inspiration you feel when you consume self-help content activates the same neural pathways that are activated when you actually do the things you’re learning about. You get a surge of dopamine from the anticipation of change, and your brain confuses the consuming insight with the enacting insight. The hamster wheel of content consumption is a roundabout and comforting way to accomplish nothing, while scratching the itch of accomplishment. Rather than reprogramming the habits that limit your potential, your habit becomes consumption itself, and you settle into a ritual of imagined transformation.

The sheer volume and chart-topping popularity of self-development content combined with the density of wisdom contained in so much of it, underscores the fact that ideas are being consumed at a rate that far outpaces any human’s ability to integrate them.

To escape the spiral of pseudo-progress you must pick one book and read it with biblical devotion — at the exclusion of everything else, for around a year.4 Biblical devotion is described in paragraph two, above. Re-read it and replace the Bible with your book of choice. You could even dial it back by about 75% and still get astonishing results, as long as you cut out other self-improvement books and stopped listening to infotainment podcasts.

Finding your self-help Bible

Let’s imagine how this works. If you read Deep Work by Cal Newport twenty-four times in a year and listened to the audiobook on all of your commutes, and studied it as seriously as a seminary student studies the bible, it would redefine your identity, and reprogram your relationship to work, time, and attention. This is a salient example, because Deep Work doesn’t provide comprehensive solutions to the problems of distractibility and focus, but it’s perfectly solid, and proven, and the author is believable, and if it became your religion for a year it would improve your concentration and prioritization to a degree that would seem unfathomable to you now. You’d feel the coach-like presence of Newport at all times, and your life would change in a meaningful way. Much more permanently than if you read several hundred of history’s most influential self-development books in a year. Deep Work is a random example; everything above holds true for The Courage to Be Disliked, or Outlive, or The Magic of Thinking Big, or an uncountable number of other books.

So how do you pick the right book to make this kind of hardcore commitment to? And how do you avoid unsubstantiated or mediocre self-help slop? This is actually very simple, just ask a few basic questions: What is holding you back, more than anything else, from having the life you want? Which author has solved your problem or done what you’re seeking to do? Have they done it multiple times, or over a long period of time? Can they clearly and convincingly explain how they did it? Have other readers used the author’s system to replicate their results? There are so many options in every sub-genre that you should have no trouble finding a book that meets these requirements. And you don’t need to pick a book you haven’t read. In fact you probably shouldn’t. You’ve almost certainly read several books that ‘hit different’ — which you promised yourself you’d re-read and actually enact. Depending on your current priorities, those might be the perfect books to return to.5

Tony Robbins isn’t Jesus, but...

This whole ‘religious devotion’ proposal isn’t entirely theoretical. I did something like it once and it worked in a life-altering way that I can still barely believe. I was twenty-six years old and I’d graduated from college with a literature degree and so I felt a reflexive condescension toward the language of self-help. But for reasons I can’t remember now, my roommate, Tim, and I decided to go totally self-help-gonzo in one of the many social experiments we were conducting at the time.

I said to Tim: “What do you think would happen if we picked one of the seminal, canonical self-help books and suspended-disbelief and just straight up did everything it said to do? Earnest, cult-like buy-in. No smirking.” He thought self-help larping would be funny, and so we chose Awaken the Giant Within by Tony Robbins without even reading an Amazon review or the back cover of the book. We chose it because of Robbins’ legendary stature in the self-help world, and because of the book’s role in his ascent. It turned out to be a paperback infomercial full of exclamation-pointed headlines like “Decisions Shape Destiny!” It encouraged incantations and it contained trademarked concepts like Neuro-Associative Conditioning™ (NAC). But we never cringed at the hyperbolic language or the acronyms, and we never flinched at the on-the-nose anecdotes. We surrendered ourselves to it, completely.

We met weekly to discuss the book, chapter-by-chapter, and we pedestaled the ideas and deconstructed them with academic rigor. Robbins said to take ‘cleansing breaths,’ so that’s how we breathed. We visualized our success. We ‘primed’ our nervous systems and chanted morning mantras. Unsurprisingly, Robbins had a lot to say about goals. And so we made a list of stretch goals — really wild and unreasonable goals — and gave ourselves a year to complete them.

We posted them outside of our rooms, and our chutzpah and determination grew with every item we ticked off. These goals and the language of Tony Robbins became the organizing forces of our lives. By the end of the year we’d crossed off nearly every item on our list of goals, and a lot more. Most of the items had to do with realizing our professional and personal potential (growing a business to $1M; writing a dissertation; feeding hundreds of homeless people, etc), but there was one, three-parted wild card item that we’d included purely for the thrill, and to see how far we could push the goal-setting idea: Sneak into the Super Bowl, the World Series, and the NBA Finals, in a calendar year.

February came, and we snuck into the Super Bowl (long story). It was among the most highly secured events in American history, so at this point we really began to believe that Tony Robbins’ was a genius for helping us understand how malleable the world is.

In April, the NBA Finals was upon us: a larger-than-life showdown between Steph Curry and LeBron James in their prime. We drove to Oakland, and we snuck in, and we sat in some of the best seats in the stadium, and when the game was over we slipped past security and stepped onto the court to soak-in the experience fully.

As I bobbed around players and coaches at center court, I turned around to look for Tim and I spotted him by the free-throw line. He was beaming, gesturing wildly, deep in conversation with the only person bigger than the athletes surrounding us: our guru, Tony Robbins. I jostled past the media and joined them. I told Tony an abbreviated version of our story: that we were reading one of his early books and taking it seriously — that because of him, in a matter of months we’d accomplished an unimaginable amount and had dozens of unforgettable experiences, including this one. It was a comically surreal full-circle moment: here we were in this preposterous place having a lifetime memory, thanking the author of the book that led us to the place where we were meeting him.

Principles

My year of Tony Robbins proves that the real way to help yourself is to pick one book and take it seriously, because Awaken the Giant Within is incredibly cheesy, a bit of a sprawling mess, and if I’m honest, not particularly special — and it nevertheless changed my life in a permanent way. It changed the way I thought about goals, and changed my view about what is possible when you set unreasonable goals and focus on them with unwavering intensity. The book worked because it weighed on me everyday in a meaningful way, because I thought about it when I made decisions, and I committed to the ideas and didn’t let anything stop me from manifesting them. I didn’t breeze through it before hurrying on to the next book. I highlighted it like a maniac, annotated it like a Bible scholar, and practiced what it preached.

But in the aftermath of that transformative year, the lesson I extracted from the experience was the wrong one: I thought that it was the book and the genre that had changed my life, when in fact it was my way of reading the book that caused the transformation. After that year, I stepped on the treadmill of pseudo-progress and began reading business books for sport and listening to podcasts in all of my downtime. I traded depth for breadth, and spent a decade floundering in the shallows of self-development — reading and consuming endlessly, integrating almost nothing.

Recently, I found myself contemplating the way devout Christians read the Bible and how it changes them, and it helped me understand what had really happened with Tony Robbins. Not long after that, I took a single book off my shelf and put away all the others. I’m now on my fourth re-read of Principles by Ray Dalio, and by this time next year I expect I’ll have read it at least twenty-four times. This year, instead of podcasts, I’ll listen to the Principles audiobook over and over again. I’ll read it in the mornings and I’ll annotate it extensively. I’ll set up and maintain and habitualize the systems Dalio describes. I’ll commit significant portions of the book to memory. I’ll overlay Dalio’s ideas onto my life like an algorithm, and I’ll get beyond rote knowledge into deep, intuitive understanding. I’ve chosen Principles for several reasons. Among them: I’m building my next business and I believe the business will be stronger if I’m able to program Dalio’s systematic approach to decision making, radical candor, and meritocracy into the DNA of my company at a foundational level — but that’s a me thing.

You should think about how you want your life to change over the next year. Then you should find a book written by someone who has a good explanation for how they got the thing you want, and you should make it your mentor, your Bible. What do you think would happen if you stepped off the hamster wheel of self-improvement, and muted all the podcasts — if you picked just one book and took it very seriously? Don’t you think it would change your life? How could it not?

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Part I. The Tools

For the human brain, daily life is a circus of distraction.

It isn’t always possible to avoid outright interruptions, but most of what ails our attention is self-inflicted and controllable — usually the result of dopamine-driven impulses which slowly and persistently fatigue the brain’s control and command center.

To reclaim your ability to direct and sustain attention, you must take control of your environment by eliminating as many of these impulses as possible: the impulse that makes your finger twitch nervously towards a phone, or pull-to-refresh your email inbox every fifteen minutes, or check the news when the work gets hard. A curated and controlled environment can eliminate these impulses by putting you on the counter-offensive, and it can be designed by blacklisting predictable distractions, neutralizing impulses, and quieting rumination.

To help you establish environmental control I’ll return to the terminology and concepts from my earlier post about the three systems of attention — the lighthouse, the prioritizer, and the flashlight (they’re re-explained below). Eventually I’ll share advanced methods of rehabbing and conditioning these three systems, but below I’ll share the simplest ways of supporting each system: how to dim the lighthouse, assist the prioritizer, and intensify the flashlight.

Housekeeping note: Below you’ll find an explanation of each of these concepts and a corresponding table of tools (plugins, apps) that relate to each concept. In Part II of this post, you’ll find a more detailed explanation of each item (how to set it up, etc). This is the least overwhelming way I could think to organize so many resources.

Dimming the Lighthouse 

The lighthouse is the part of your attentional system that is responsible for scanning your external environment and your internal landscape. It doesn’t make decisions about what you pay attention to (the prioritizer does this), it just observes everything around and inside of you and creates a buffet of options for your prioritizer to select from. Here are some of the things your lighthouse might notice: personalized ads that follow you around the internet — moving and blinking and reminding you of shoes you almost bought three months ago. Group chat messages that bing and buzz in your pocket like an M16. An irresistible impulse to check if there is new news — political news, sports news, industry news. Your lighthouse notices all these things at once (and way more) and shares them with your prioritizer, and your prioritizer chooses what to direct your attention toward.

In our modern environment, the lighthouse picks up mostly noise and very little signal, and this forces your prioritizer to make unnecessary decisions about what to focus on.1 You must put firm controls in place to remove the unimportant things; otherwise, over time your prioritizer gets decision fatigue and begins making less disciplined decisions about how to allocate attention. One of the most helpful and simple things you can do to improve your ability to maintain focus is to ‘dim your lighthouse’ — dull your ability to pick up external stimuli and reduce your chances of internal thought loops and rumination.

There are many ways to do this: through ad and newsfeed blockers, email filters, heavily gated phone notifications, added friction for social media apps, a lean news diet (or total news sobriety), noise canceling headphones combined with ‘brain music,’ and more. Your lighthouse can’t relay an opportunity for distraction that it isn’t aware of.

Below is a list of resources and tools for dimming the lighthouse. I use most of them daily. This list alone (after a week of consistent use) can improve your focus baseline by roughly 2,500 basis points.

*The recommendations in the top three rows are essential to improving focus. Specific instructions for each row are in the bottom section of this post.

Assisting the Prioritizer

The job of the prioritizer is to consider all available options and direct your focus flashlight on the one thing that matters most in the present moment. After you’ve ‘dimmed the lighthouse’ using the tools above, the best thing you can do to support your prioritizer is plan ahead. You can do this by setting ‘automatic rules’ for yourself and then leveraging tech tools to help make these rules habitual.

An automatic rule is a decision you’ve made ahead of time about how you will behave in a certain situation, so that you can avoid making decisions when the conditions don’t support your best intentions. An example: you regularly succumb to an impulse to check the news throughout the work day, so you create a non-negotiable, automatic rule for yourself to override the impulse: I’m not allowed to check the news until after 7PM and for no longer than 15 minutes. This makes your prioritizer’s job a lot easier — it never needs to decide when to check the news. But of course the impulse to check can easily overwhelm an aspirational ‘automatic rule’ and cause you to negotiate exceptions with yourself. To prevent this, there are web apps you can use to blacklist websites within predetermined time frames (or blacklist websites entirely). When the compulsion to check the news overcomes you and you try to break your rule and pull up The NYT (or any news site), you’ll arrive at a dead link. You can also set up your own keywords. For me, any web page with the words “musk” or “trump” is blocked.

Over time, I’ve created automatic rules to protect against every encroaching impulse, and I’ve found different tools to reinforce each rule. Below is a table full of applications, plug-ins, and device setting recommendations which have been curated to enable pre-decisions and support automatic rules for how my higher-self would allocate attention.

*Again, detailed instructions and notes for everything below is in Part II

Intensifying the Flashlight

The flashlight is the attentional system that actually does the focusing. When your prioritizer points your flashlight at something, it creates a beam of light — a tunneling type of concentration. That narrow beam of light is surrounded by an infinite expanse of dark. Whatever your flashlight is pointed at is what you’re focused on. The dark stuff is everything else that you no longer notice. You only have one flashlight. You can’t focus on two things at once.

Sustained attention has less to do with the brightness of that flashlight’s focus than with supporting a disordered prioritizer which jerks the flashlight around. Your flashlight is already bright enough to achieve your most ambitious goals, and to my knowledge there aren’t many things you can do to actually increase the intensity of your flashlight’s beam much. This is why most of our energy should be directed towards improving our environment to ensure that our flashlight simply remains fixed on the right things.

That said, there are two things that seem to improve the brightness of the focus beam: sleep and stimulants. When you’re sleepy, you can start to feel your flashlight dimming — it is difficult to focus because your prioritizer makes worse decisions when you are sleep deprived, but the object of your attention also takes on a blurrier, dimmer, duller quality. It goes in and out of focus. The flashlight flickers. We’ll deal with sleep later — as it is a core pillar of focus rather than an environmental quick fix.

Stimulants, on the other hand, can help you right away. Stimulants do many things, and I am not a neurologist so I won’t attempt to explain all of what they do in language neither of us understand, but one straightforward thing they do is block receptors in the brain that promote sleepiness and relaxation.

Caffeine is obviously the most commonly consumed stimulant, and it’s a quick and easy substitute for natural rest. There’s no question that it can help improve attention at the right dosage. On the prescribed end of the stimulant spectrum there are ADHD drugs like Adderall or Ritalin. I don’t know very much about these drugs, other than the fact that they do work quite well, and that they also create chemical and emotional dependencies among numerous other side effects. Part of my intention in deep diving into the world of concentration was to discover whether an alternative to drug-enabled attention was possible — and now I’m confident that it is.

There are also a few other so-called ‘brain-enhancing’ supplements that fall into the flashlight-brightening category — including supplements that allegedly improve cognitive function (I’ve experienced mixed results), and ‘neurostimulating’ background music that is designed to harmonize with optimally ‘focused’ brainwave frequencies (surprisingly, I’ve experienced strong results).

Part II. Setting Up the Tools

Below is a breakdown of how I use everything above. My recommendation is that you start at the start and work your way down. You don’t have to download every one of these apps and plug-ins or make all of these changes to your phone and computer settings, but I strongly suggest that you make many of them. The suggestions here are mostly optimized for the situation I am familiar with (iPhone, MacBook, Chrome Browser). If you have specific questions about how to leverage similar apps/plugins/blockers, for situations that aren't mentioned here (like Android or Safari or TikTok), do some Googling and I’m sure you’ll find the exact tool you need to solve your problem. If you’re stuck, leave a comment and I’ll try to help you find what you need.

If you want to make an app less addicting there is always a solution, you simply might not like the changes it requires you to make.

Dimming the Lighthouse

STEP 1: Phone / Computer Management

1. App Notifications: Adjusting mobile/desktop notification settings is essential. My overarching principle is: you must remove all red notification bubbles, home screen notifications, bouncing dock icons, sounds, buzzes, and vibrational haptics. On your iPhone and your computer, you’ll navigate to Settings > Notifications, then beneath the “Notification Style” header you’ll see a list of every app on your phone. With very, very few exceptions I click into each one and toggle “Allow Notifications” to off.2 Exceptions include things like Uber or Doordash, where it’s important to receive time-sensitive alerts about a ride or delivery. You may have a few of your own exceptions, but I would strongly advise against making many. Take this further than you think you can, and if something becomes a problem just reintroduce notifications for that thing. 

2. Messaging Notifications: Within notification settings, the most personal, unique, and high leverage apps to mute are communication apps: Messages, Phone, FaceTime, WhatsApp, etc. I recommend extreme measures. My belief is that being extremely and immediately reachable at all times is a twenty-first century construct, and it contributes hugely to society’s rising attentional-deficiencies and collective sense of overwhelm. Make yourself harder to reach. It’s okay.

   1. Messaging, Phone: I hide red bubbles, silence notifications, and check messages proactively, rather than reactively. This is one of the highest leverage things you can do to protect your attention. If you are committed to staying on top of group chats in real time, I’m not sure that you have any chance of solving your attention problem. You are essentially asking your prioritizer to do a job that it was not designed to do and is incapable of doing: triaging your attentional resources while maintaining an engaged presence in an endless, chaotic group conversation (often many conversations). I highly recommend turning all Messages notifications off, and switching to a proactive, batched communication style at set times of the day. Even when I have 17 text messages, I never see a red notification bubble above my Messages app, which means that I have to open the app to see whether I have messages. This is especially useful when you pick up your phone to use it for something specific and intentional, like making a phone call — because you won’t get derailed by curiosity about a notification, and switch your attention to checking and replying to your texts. If your prioritizer doesn’t know there are texts, it won’t have to decide whether to direct your flashlight towards checking them.

   2. Messaging, Computer: taking things one step further: I highly recommend removing the Messages app from your computer — ie. just straight up switching the iCloud connection off. This is in my personal top 10 list of most effective ways of protecting attention. This means that you’ll only be able to use your phone to text, and you can block off time to do that in batches. It prevents me from spending time sending super long texts because I don’t like texting with my thumbs (they move way slower than my thoughts). When I have a laptop keyboard to type from, I tend to send unnecessarily long texts. On your computer, go to Settings > iCloud > Messages > Off. Do it and don’t look back.

3. Messaging, Other (WhatsApp, Viber, Telegram, FB Messenger, et. al.): I recommend treating these as above. Hide and silence all notifications from your phone. Delete the desktop apps. Use each app proactively rather than reactively. Check them on an as-needed basis.

3. Phone Notifications: I use the Do Not Disturb feature on my phone to limit real time, unexpected calls to a small group of people. Otherwise, my phone doesn’t ring. One of the most intrusive and annoying things in the entire world is being finally focused on something and getting derailed by a spam call. This problem is solved by Do Not Disturb. If you’re expecting a call from someone who isn’t on your exception list, you can just toggle Do Not Disturb off temporarily. Otherwise, I have it on at all times. It is easy to set up an exception list in Settings > Focus > Do Not Disturb > People > Allow Notifications From > then add people you want to allow through the filter. This all applies to FaceTime as well.

4. Slack, Teams, Work Messenger Apps, etc.: I can’t go through each of these one by one, and it’s more difficult to prescribe broad solutions here because it’s an area where you may feel like you’re not allowed to mute and manage inbound notifications. As with everything else above though, I would advocate adjusting your settings to make yourself much more difficult to reach, and to experiment with keywords and filters that ensure you don’t miss the urgent things. Here is a resource for customizing notifications on Slack. When set to default, Slack (and similar apps) make it very difficult to accomplish important, deep work over long interrupted periods of time. There are valuable use cases for work chat apps, but I’ve grown increasingly skeptical of Slack as a net-positive productivity tool, and I would advocate batching work communication, silencing all but urgent notifications, and limiting your use of it. And you should delete the mobile app. Your business’s goal should revolve around business output and productivity, and being easily interruptible is extremely counterproductive to both.

STEP 2: News Management

• The Problem: Henry Thoreau: ''Hardly a man takes a half-hour's nap after dinner, 'but when he wakes he holds up his head and asks, 'What's the news?'''

  Also Thoreau: “And I am sure that I never read any memorable news in a newspaper. If we read of one man robbed, or murdered, or killed by accident, or one house burned, or one vessel wrecked… we need never read of another. One is enough. If you are acquainted with the principle, what do you care for a myriad of instances and applications?”

  Thoreau is right. I plan to write about this issue in an entire separate and specific essay, but the important thing to know is that (1) the news is sensational by design (the news industry depends on advertising; advertising dollars are correlated to reach/engagement; and reach/engagement are dependent on sensationalism, extreme partisanship, and fear-mongering), (2) the sensational nature of the news produces an addictive response, (3) negative news lingers in your mind, in a distressing way, long after you read or encounter it. When you are in distress, it is extremely difficult to focus. I’m convinced that opting out of the news cycle will have no legitimately negative impact on a person’s life, and countless positive impacts. You will be less enraged, less scared, less cynical. Ironically, there is a very high chance that you’ll be less misinformed.

  I have been news sober for 14 months (with occasional relapses). It has done wonders for my attention. I urgently recommend news sobriety. If something is genuinely important enough, you’ll hear about it. Our brains didn’t evolve to manage the empathetic overload caused by real time play-by-plays of a war happening on the other side of the world. I welcome anyone to challenge me on the importance of maintaining regular contact with the news cycle.

• Recommendation: I recommend going cold turkey on the news — not watching it on television, blocking websites, not reading newspapers. Try it first for a week and see how you feel. If you feel better, try it for a month. If going cold turkey is too extreme I recommend blocking it during certain times of the day, as much as you’re comfortable with, and using tools like Self Control and Blocksite to support you. They are explained in more detail below.

STEP 3: Social Media Management

• What: My thoughts about social media are essentially identical to the perspective shared above about the news. Like the news, social media: (1) algorithmically prioritizes sensational content (Facebook, et. al. depend on advertising; advertising dollars are correlated to user engagement, strong user engagement is highly correlated with content that invokes rage, division, fear, and dopamine release), (2) the sensational nature of social media content (in addition to all of the other addictive features designed into social media interfaces) produces a dependency, (3) negative news and cheap entertainment lingers in your mind, in a distressing and distracting way, long after you read or encounter it.

  The negative and distracting impact of social media have been so heavily covered that I won’t belabor the point. There are some benefits, and there are ways to get the benefits without many of the drawbacks but it requires strong boundaries.

• Recommendation: I recommend removing social media from your life to the greatest extent that you can. For platforms that you genuinely feel add value to your life after serious reflection, I recommend removing the apps from your phone, and accessing them only during short, predetermined periods on your computer. Something like 15 minutes per day maximum. 

  • Note: Substack is increasingly developing into a social platform and it should be treated like one. I personally recommend deleting the app from your phone and limiting engagement with Notes to pre-determined periods.

AdBlock 

• What is it?: AdBlock is a Chrome plugin which removes basically all ads from the internet. It makes your computer faster, and it allows you to browse the web without being derailed by banner and interstitial ads. If you are meaning to read something, and a blinking advertisement steals your attention — that’s an avoidable distraction, and it’s an even worse distraction if you decide to click on the ad. Hide the ads. It’s free, and it’s a game changer.

• Recommendation: Install it. There is not much else to do, it works its magic in the background.

Adblock for YouTube

• What is it?: YouTube developed a way of identifying and blocking AdBlock from working on ads before, during, and after videos. This Chrome Plugin is a free workaround. Basically an add on to the plugin above. After you set it up you’ll forget that most people watch ads before YouTube videos. Crazy.

• Recommendation: Install it. Stop seeing ads on YouTube.

Blank Spaces Launcher

• What is it?: This iPhone app uses a widget to make your phone look like a Kindle. No icons, no notification, no saturated colors, no mess. There are several competitors, some of them free. Use any one of them. It makes your phone less distracting, and you can still pull down to search for apps as you need them.

• Recommendation: Your options are: the screen on the left or the one on the right. Which one is more likely to distract you? It’s important to stop thinking of your phone as your friend, when it’s really your enemy. Make it feel like a utility.

Unroll.me

• What is it?: An email plug-in which identifies all email newsletters and lists that you’re subscribed to and gives you three choices: (1) selectively opt-out of all of email lists that you no longer want to receive emails from (or didn’t know you were even subscribed to), (2) continue to receive emails from specific senders, as before, and (3) roll specific emails into a daily brief — so they’re all in one place, rather than separate emails that clog your inbox and make it more difficult to get in and out of your email client. Your email inbox can be a place where you get things done, or a place where you’re yanked around by other people’s priorities — make sure it’s the prior.

• Recommendation: I personally don’t use the ‘roll-up’ feature. I recommend simply connecting it to your email account so that you can see, all at once, the lists that you’re subscribed to — within 5-10 minutes, you’ll be able to unsubscribe from hundreds of unnecessary subscriptions at once, and calm your inbox down.

Unhook

• What is it?: This is one of the best kept secrets on the internet. YouTube is full of addictive, attention-grabbing, time-draining features like autoplay, video recommendations, comments, and the home feed. With Unhook you can hide basically everything and make it look as simple as the Google home page — with just a search bar. Once you find the video or tutorial you were looking for, the right hand column won’t be cluttered with thumbnails, click bait video headlines, and comments — it’ll just show you the video. That’s it. And there won’t be ads because of Adblock for YouTube. This is what my YouTube home screen looks like and so should yours:

• Recommendation: I strongly, strongly recommend downloading the Unhook chrome plugin and essentially hiding every feature except the search bar. It’ll crater the amount of time you spend getting sucked into YouTube rabbit holes, and will allow you to simply get what you came for. The only things I leave untoggled in my settings are “Hide Video Info” and “Hide Top Bar.” My settings are below.

Antigram

• What is it?: Antigram is a Chrome Plugin for using Instagram on your computer. My super strong recommendation is to remove Instagram from your phone, and only access it from your computer (occasionally), and to use Antigram to limit the addicting features of Instagram.

• Recommendation: Antigram can hide “Reels”, “Explore” page, “Stories”, “Suggestions,” and “For You” — essentially the features which keep you scrolling endlessly. I almost don’t think of Instagram as addicting anymore because I’ve eliminated all of these features and don’t have the app on my phone. It’s actually kind of boring. I check it about once per week. When I do it’s for a few minutes. I have blocked everything except for the posts of people and brands I follow. I also personally recommend unfollowing all meme accounts — they mercilessly drain attentional resources. Settings below: 

Control Panel

• What is it?: Control Panel is a Chrome Plugin that allows you to customize the way Twitter/X looks. It can remove follower counts, retweets, and other vanity metrics; it can also remove recommendations, the “For You” Page and all kinds of other distracting features. You can essentially remove anything and strip it all the way back. You can even replace the X branding with Twitter branding if you’re nostalgic or anti-Elon.

• Recommendation: I don’t use Twitter/X much, but I know how addicting it can be. I strongly recommend using this plugin if you use Twitter, and anytime you catch yourself being sidetracked or mindlessly browsing or wasting time — adjust or remove the feature that caused it. You’ll eventually have a platform that serves your intention way more than it is currently designed to. It won’t remove the insane polarization and rage, so it’s best to just put boundaries around Twitter/X usage in general. And cut it out if you can.

LinkOff / Feedblocker

• What is it?: At some point LinkedIn became a social media platform for super cringy semi-work related personal updates, mostly from people who aren’t even in your network. The features I found most addicting and distracting were the news on the right side, and the news feed. I use Feedblocker (a Chrome Plugin) to remove both. Now there’s literally nothing to do on LinkedIn except the boring professional work that I visited the site to do. Which is great. (Nb. it looks like Feedblocker is no longer being supported as of 10/25, but it still works for me; try LinkOff, which serves the same purpose).

• Recommendation: Strongly recommend downloading if you ever use LinkedIn. Set it up once (couldn’t be more simple), and make LinkedIn LinkedIn again.

Newsfeed Eradicator

• What is it?: A Chrome Plugin that replaces your Facebook Newsfeed with an inspiring quote. I don’t use Facebook, but there are likely more settings that you can adjust to remove other addicting features. If you do find yourself distracted by Facebook and this plugin doesn’t help, keep searching for one that does — my assumption is that Facebook would be one of the easiest platforms to modify using plugins. This plugin also works for other platforms, though I use the tailored plugins, described above, for more control over each platform.

• Recommendation: Download it and remove your Facebook News Feed.

Socialfocus

• What is it?: A Mac Desktop app which does a lot of the same things as the plugins above (combined), but for Safari. I have no experience with this app, since I use Chrome as my browser, but it appears to have many of the most useful features described in all of the plugins above.

• Recommendation: If you browse with Safari, I’d spend $2.99 to try this out and see if it works as a one stop shop.

Noise Canceling Headphones

• What is it?: Just what it sounds like. You’re a lot more difficult to distract when you can’t hear what’s going on around you.

• Recommendation: I use Apple AirPods Max headphones and they block out noise well, but there are other options that are cheaper and reportedly block out noise even better. Do some research and do yourself a favor and get some. Don’t get on-ear headphones, get full ear covering headphones. Airpods Pro headphones work well, but not even close to as well. I recommend pairing with Brain.fm (covered below).

Assisting the Prioritizer

Self Control

• What is it?: A Mac app which allows you to block websites for predetermined periods of time. 

• Recommendation: There are a few apps that do this, including Freedom. I use Self Control because it is the most hardcore version of the app that I could find (and it’s free forever). There is no escape button. Once you make a commitment you can’t undo it without hacking into your computer settings. I have a list of about 20 websites that I’ve found myself browsing mindlessly over time — mostly news websites, and sports websites. All of these are on my blacklist, and I frequently set a 40 day block (by extending the block in 24 hour increments, all at once). By the end of a 40 day ban, I’ve essentially broken the habit of looking up the news. I strongly recommend using Self Control. You can also add social media websites to the blacklist.  

Freedom

• What is it?: Essentially the same things as Self Control, but with more features — including ones that make it easier to override your commitments. It’s less hardcore and less effective than Self Control. And you have to pay for it. But it does work across your phone and desktop, and for Mac, PC, iPhone, and Android.

• Recommendation: I recommend Self Control, it’s simpler and more effective for me, and it’s free. But Freedom does have some features that may fit into your plans better (like scheduling when you can and can’t use websites, and website blocking across devices).

Blocksite

• What is it?: Similar to the apps above, but a Chrome Plugin. It allows you to block search terms on Google, and block any website that has the terms that you block. And it has a lot of other features.

• Recommendation: I found this app because I needed a supplement to Self Control which would effectively stop me from searching for “election news” towards the end of 2024. After installing it, and adding keywords, anytime I searched for “trump” or “kamala” — web pages containing those words wouldn’t load. It’s crazy how much attentional savings are downstream from blocking any web pages that use the word “trump.” I currently use the free plan, which limits the number of words I can use, but I still find it super helpful as a backup measure for Self Control.

Mailman

• What is it?: Mailman is a web app that connects to your email account and allows you to essentially batch emails so that they only arrive in your inbox at predetermined times. This means there is no reason to refresh email repeatedly throughout the day. My emails deliver twice per day: at 8:30AM and 4:30PM. This is one of the most effective automatic rule I’ve created for myself. The compulsion to check email at all times went away surprisingly quickly when there was nothing new to see in my inbox outside of these preset times. With Mailman, you can also set rules within rules, like adding VIP senders (friends, family, boss, etc) whose emails are able to bypass through the filters and reach you. And you can reply to email anytime. This app has helped recalibrate my sense of urgency — it’s vanishingly rare that anything in my inbox requires immediate attention, and yet I used to regularly derail work and leisure time by refreshing my inbox throughout the day.

• Recommendation: I recommend downloading the app and using the free trial. Set up some VIPs, and start with two email delivery batches — morning and late afternoon. Then work through email twice per day in big batches. Batching is a proven way to efficiently and effectively manage communication. When my free trial expired, the settings remained connected to my inbox, so I’m still effectively using the app for free — but I can’t change the settings now. This works out pretty well, though I’d happily pay for it if forced to.

Read Later Apps (Instapaper, Readwise, Pocket)

• What are they?: There are several “Read Later” apps and they all work in more or less the same way. They allow you to save an article for later, instead of reading it right in the moment or forgetting about it forever. This relates to attention in that it’s not uncommon that someone will send me an interesting article in the middle of the day, and I’ll feel compelled to read it right then. This derails me from the thing I meant to be paying attention to. All of these services make it super simple to save articles so that you can batch read them when you have time set aside for that sort of thing — rather than reading things as they enter your orbit.

• Recommendation: I use Instapaper. The free version allows me to save as many articles as I’d like. I don’t need any of the paid features.

Ksafe

• What is it?: Ksafe is a timed locker made to fit your phone (or anything else that might distract you). When the timer goes off you can remove the lid and retrieve your phone.

• Recommendation: I’ve never used Ksafe, and I think it’s redundant and unnecessary if you follow many of my other suggestions and keep your phone out of your line of sight. But some people certainly like it, and when you still have your training wheels on it may be helpful just to hide and lock your phone from yourself when you really need to focus.

Brick

• What is it?: Brick is a little piece of hardware that connects to an app that essentially acts as a lock and key for distracting apps on your phone. You set up your phone to block pre-selected apps, and then tap the ‘brick’ and it locks you out of those apps. You can then give the ‘brick’ to someone or put it in another room, and you’ll be locked out until you tap the ‘brick’ again. 

• Recommendation: I haven’t used Brick, but it’s something like a software powered version of Ksafe. I can see several scenarios in which it could help someone avoid distractibility by leveraging social accountability. If you follow many of my other recommendations you won’t need a tool like this to stop yourself from using your phone, because there won’t be many reasons to use your phone or many apps to block yourself from. I can see how it’d be good for families that struggle to manage phone use with their kids.

Forest

• What is it?: Forest is a mobile app (iPhone and Android) that gamifies focus by using the mobile gaming mechanics that are typically used to make games addictive. You set a goal and a timer, and a tree begins growing on your screen while you focus on your goal. If you lose focus the tree dies, if you stay focused you add a tree to your forest. The idea is that you’ll be motivated to grow a big forest full of fully mature tree goals. 

• Recommendation: I’ve never used Forest, but it’s a popular app and it came up in a few of the books that I read about systems of attention and focus. At some point I plan to try it, mostly out of curiosity and for research, but I haven’t found it necessary for managing my attention. It feels gimmicky to me; sort of like an emoji-ish tamagotchi accountability partner. It certainly does seem to work for people though.

Light Phone / Dumb Phone

• What is it?: Light Phone is a low-fi second phone that you can take with you on the go, in order to be reachable and to have access to a modern phone’s most useful and essential features — but it is in black and white sort of like a Kindle, and it is super stripped down. A dumb phone is a flip phone, or similar. Both can serve as temporary (or long term) replacements of your smartphone, to help you break unhealthy attentional habits — which is the most addicting and attention-draining product that has ever existed.

• Recommendation: I haven’t used a Light Phone but it has been on my radar for a while and I’ve flirted with the idea. I recently began experimenting with a combination of an Apple Watch and one of these — and I’m trying to fully substitute my phone out. Depending on how this goes I’ll report on it at some point.

Interval Timer

• What is it?: One way to ‘assist your prioritizer’ is to train yourself to be more conscious of how your prioritizer has decided to allocate your attention. One of the ways our attention span breaks over time is that we stop noticing when our attention has wandered — it’s easy to find yourself scrolling or browsing the web for 30 to 45 minutes on accident. The easiest way to avoid this is to continuously set a timer for 15 or 30 minutes while you’re working. This trains you to become more conscious of the passage of time (a huge issue for people with ADHD), and if your attention has drifted away from your priority, it serves as a reminder to come back to center.

• Recommendation: I like to set a timer to go off at the x:30 and x:00 of every hour when I’m working. I regularly reset the native ‘clock’ timer on my laptop (or I use Horo Timer) — adding 17 minutes if I’m starting a task at 1:13PM for example, then 30 minutes when that timer goes off, and so on. Unbelievably, this super simple habit is among the top 10 most helpful things I do to maintain and improve my attention. It trains you to notice if your attention is drifting.

Removing Phone from View

• What is it?: This is super simple. If you remove your phone from your view, it’s so much easier to get in the zone. Phone visibility alone has been proven in several studies to reduce the brain’s capacity to hold and process information. Even when the phone is on silent or turned off — cognitive load is higher when a phone is visible. There is even an established correlation between how close a phone is to your body, and how well you can focus. 

• Recommendation: When you really want to focus, put your phone in a different room. It makes a big difference. If it needs to be around because of an expected call or for some other reason, make it invisible.

Deadlines

• What is it?: Even when my attentional deficiency was at its worst, a deadline always did wonders in allowing me to pull myself together and maintain deep, unbroken concentration. A deadline essentially crowds out other priorities, and it is a forcing function for focus and prioritization, but it can be difficult to fake a legitimate deadline. The closest thing that you can do is to publicly commit to someone (whose opinion you care about) that you’ll finish something by a specific time, and it is helpful if you raise the stakes by promising to Venmo them (an amount that would hurt at least a bit) if you don’t.

• Recommendation: I often use false deadlines and an accountability partner when a project doesn’t have actual deadlines. It is not a bulletproof strategy, but it’s definitely more helpful than nothing.

Phone Settings - Removing Apps:

• What is it?: Your prioritizer is at its best when it has the least to do. The best thing you can do to support it is to pre-decide that you’re not going to use distracting, attention-draining, addicting phone apps. The closer you get to making your phone dumb again, the better off you’ll be. Phones used to be just phones. It is possible and rewarding to create a world for yourself in a world where they are mostly just phones again. Go through every app on your phone and ask yourself the question: “Is it plausible that I could spend 15 consecutive minutes using this app on accident” — this will allow you to quickly sort between: apps that have a utility that serves you, and apps where your attention span is being preyed upon. Ultimately, you’ll have to independently make a decision here about what you’re comfortable deleting; below are just my recommendations. 

  • Mobile Games: Delete all mobile games from your phone — even so-called brain games.

  • Social Media: Delete all social media apps from your phone. If you want to use social media, use it on your desktop (where you can put controls around it with Chrome Plugins)

  • Internet: Delete internet browsers from your phone. Delete Google, Chrome, etc, and disable Safari. To disable Safari: Open Settings > Tap Screen Time > Select Content & Privacy Restrictions > Tap Allowed Apps > Enter your Screen Time Passcode > Toggle Safari to the off position. You can’t technically delete Safari, but this makes it undiscoverable, essentially inaccessible, and it will not be able to launch a page. This is among the most extreme things I do, but the payoff is huge. Sometimes I have to redownload Chrome when I’m on the go and need to look something specific up, but this is fine: I download it, get what I need, delete it. And usually I can just borrow someone else’s phone. This is on the Top 10 list of highest leverage things I do to improve my attention.

  • Email: Delete all email applications for your phone, and disconnect Apple Mail on your phone so that the app doesn’t work. This one is really hard for most people, and it was difficult for me at first, but it has been a total game changer. Since you ought to be batch replying to email anyways (using Mailman), you shouldn't have a need to check your email constantly on your phone. It’s an attention drain.

  • Thumb Twitchers: if you’ve deleted all of the apps above, you’ll find it interesting to see what your thumb twitches towards when you take your phone out of your pocket. I overheard someone at the farmers market the other day say: “I deleted Instagram, so now I just scroll the weather.” I’ve been there. It takes a while to rewire the brain so that the addictive impulse to mindlessly scroll through something dissipates. But it will. In the meantime, if you find yourself gravitating towards and using apps as a way of distracting yourself or passing time, delete them. Make your phone dumb again.

  • Hide App Icons: I’ve recently been experimenting with Blank Spaces Launcher, but prior to this I’d deleted nearly every app from the main screen of my phone, so that my eyes aren’t drawn to the wrong apps when I take my phone out to do something specific (like make a call). This is an effective way of pre-deciding that you want to use your phone purposefully, not mindlessly. When you need to pull up an app, you search for it in your App Library with the search bar (just pull down in the middle of you screen and it will activate the search bar). There is no need to have all of your app icons in your field of view every time you use your phone. This is what my primary phone screen looks like (background is also all black).

    

• Grayscale: One last setting that is very effective at making your phone less addicting is grayscale. On the iPhone you can press the on/off button on the right side of the phone three times quickly, and it will change everything on your phone to grayscale. It’s astonishing how much less interesting every app is when it is desaturated. I go through periods when I activate greyscale regularly.

Intensifying the Flashlight

Brain.fm

• What is it?: Brain.fm is an app which plays music that is embedded with patterned soundwaves that enhance brain activity. It sounds absurd, and I’d usually dismiss something like this out of hand, but I genuinely find that it works. And they point to abundant scientific evidence which suggests that it works. Idk. Maybe it’s placebo. But I seem do a lot of my best thinking when it is playing through my headphones. They have a free trial. You can also put a YouTube sample of the ‘music’ on continuous loop for the same effect, it’s just less convenient.

• Recommendation: I’d recommend giving the free trial a shot. If you already work to some other groove, keep doing your thing. If not, trial it, ideally quietly, with noise canceling headphones. I use it every day.

Caffeine

• A moderate amount of caffeine can help you focus because it makes you feel more alert. Sleep is a better and more sustainable substitute. If you enjoy coffee or matcha or some other caffeinated beverage, keep enjoying. 

Adaptogens

• Adaptogens are natural substances (typically herbs or mushrooms) that allegedly help the body resist different forms of stress, reduce fatigue, and enhance mental performance. Some of the more common ones are coffees, elixirs, and lattes which feature reishi, lion's mane, and cordyceps. The most popular brands are probably Four Sigmatic or MudWtr. I personally haven’t found adaptogens to be effective at improving my focus and allowing me to maintain attention, but some people apparently have, and there is some scientific evidence that they do.

Nootropics

• Nootropics are substances that claim to improve memory, creativity, motivation, and attention. They are often referred to as ‘smart drugs’ and they range from prescription (modafinil), to over-the-counter supplements (L-theanine), to herbal supplements (Ginkgo biloba). I’m no Nootropic expert but I have experimented with a few over the counter supplements. I did find Artichoke Leaf Extract and L-Carnitine to be effective, but always suspected that it was the placebo effect. They were expensive, so I’d feel more pressure to focus after taking one — it felt similar to the ‘deadline effect.’ There are Reddit forums and corners of the internet dedicated to stacking pills and supplements to stimulate focus, but this has increasingly felt to me like a way of avoiding root cause issues.

That’s all for now. If you made it this far, you can definitely develop a bulletproof attention span.

More Reading:

The Art of Attention explains why I became obsessed with attention. Your 47-Second Attention Span is an outline of the masterclass. More to follow (including an abridged version of this guide).

2

I. It All Comes Back

I’ve spent a full decade away from a basketball court and I’m standing at the free throw line now. My right foot squeaks into place on the sticky hardwood. I dribble twice, stare vacantly into the middle distance, look up to the rim, breathe out, shoot. Swish.

I shoot forty-nine more times. I count the shots, I count the makes. I make forty-four of fifty. Eighty-eight percent.1 “It’s like riding a bike,” an old coach once told me, as he made shot after shot in middle-age, with his beer gut and his bad knees, while I rebounded ball after ball. “You never lose it.”

And it’s true. You put in enough hours and it lives on inside you, even after ten years. Eighty-eight percent, after ten years.

I was simply letting my body remember. Tapping into a special knowledge of the hands, an embodied sense of physics and launch angles developed in an earlier chapter of my life. I was channeling something I’d obsessed over and mastered and made autonomic in high pressure situations. Something I could quite literally do, at one point in time, with my eyes closed.

II. Feel

When I was eleven years old, I entered the regional science fair with a logbook full of basketball drills that masqueraded as a science experiment. The project was called: “Does practice make perfect?” I’d shoot ten free throws and record how many I made, then I’d shoot one-hundred, then I’d shoot ten more and record how many I made the second time. Over the course of a few months, I observed and reported on the before and after delta. The project didn’t win any ribbons but I shot a lot of free throws, and I got good at shooting them.

This would turn out to be the first of many installments in a deliberate approach to practicing the special situations of basketball that I would employ over the next decade. I also made goggles out of throwaway glasses frames and duct tape, which blocked out the lower periphery and made it impossible to look down while I dribbled. I dribbled two and three balls at a time, juggling downward for an hour each day after school until my forearms were throbbing and my hands were black as tar from concrete and dust. I frequently dribbled basketballs that were two times larger than normal. This made the two and three ball dribbling drills diabolical. Eventually I combined many of these things while I weaved around cones at full speed. I attached rakes to trashcans and practiced dribbling around them, and shooting over them. In the summers, I often shot hoops until I could feel pain in my elbow joint. In your late teens it takes about six hours of continuous use to feel anything at all in the elbow joint.

When you add this all up, and much, much more, you develop something called feel. Across sports and across many disciplines you hear about feel. In basketball, feel is a flow state in the fingertips. Once it’s there, it lives in you forever.

Feel is acquired through a kind of pattern recognition that comes with decades of relentless repetition. In basketball, it manifests in the spatial awareness of bodies you cannot see on the court, based on the bodies you can see. And in the way your subconscious-self stretches out your hands to receive a bounce pass, so that your fingers lock perfectly into the ball’s black grooves.

It’s very comforting to have feel at something. It’s like seeing your best childhood friend after months or years or decades — there’s a warm familiarity to it. It all comes back effortlessly. Some people have feel with a piano, while carving on skis, while speaking a language they learned as a child. You’re out of your head. And that’s an increasingly rare and comforting place to be. It’s comforting, even if you rarely do it anymore.

Occasionally, I shoot free throws now — purely for catharsis, like a moving meditation. I’ve sometimes wondered, as I shoot, whether I’ll ever develop feel like this in anything else again. Whether that ship has sailed, and whether basketball — useless as it is to me now — is the only place I’ll ever have feel. At first, I thought so. Now I don’t think so.

Now I know the secret to feel, and it’s not exactly 10,000 hours. But it’s closely related. The secret to feel is something I’d been doing unknowingly throughout my basketball career: deliberate practice.

III. Deliberate Practice

Last year, I discovered the concept of deliberate practice circuitously.

I was reading “Flow” by Mihaly Csikszentmihalyi, and his concept of the ‘flow state’ turned out to be synonymous with ‘feel’ in contexts like basketball. Flow is embodied concentration, a loss of time awareness, a loss of self-consciousness — a full mind-body connectedness.2 But the leading scholarship on flow stopped short of making tactical suggestions about how to reliably cultivate feel and access it at-will.

I’d only ever felt serious flow states on a basketball court, and I wanted to know why, because I wanted more of it in other contexts.

In the subjects who experienced flow, there was a recurring element of intense, autotelic effort and ambition — while playing piano, rock climbing, painting, writing code, performing surgery. This pattern of peak performance led me to the research of Anders Ericsson.

In 1993, Ericsson published a paper that contained a concept that would eventually be oversimplified and ubiquitous: he observed that elite violinists accumulated around 10,000 hours of deliberate practice by age 20. Malcom Gladwell codified this into the “10,000 Hour Rule” in his book Outliers, and used it to explain the one weird trick that history’s famous elite performers had used to achieve mastery.

But Ericsson’s real point had very little to do with the number of practice hours, and everything to do with the ferocious intensity and very specific characteristics of those practice hours. 10,000 hours was merely a correlation, plus or minus. In an effort to correct the record before he died Ericsson wrote a book that explained his real point: the concept of ‘deliberate practice.’ The book is called Peak.

IMHO, the ideas contained in Peak make it a true human treasure. It is a source of infinite leverage. The concepts outlined by Ericsson, unlike those shared by Gladwell, really do explain the outliers of the world. It is the consummate playbook for realizing one’s personal potential and even achieving world-class mastery.

Since reading it, I have applied the concepts at various scales — in focused 10-day sprints, towards lifetime skill mastery, and in my daily work.

Here is a compressed version of the seven cornerstones of deliberate practice, which eventually lead to mastery (though I, of course, urgently recommend reading the book).

1. Well-Defined, Specific Goals - each practice session focuses on improving a clearly defined skill or sub-skill; goals should be narrow, and measurable. (eg. for writing: ‘Practice writing 10 different opening lines for the same scene, focusing on immediacy, voice, and hook’ as opposed to ‘Write for an hour’)

2. Coaching - practice should be informed by expert coaching instruction. You must seek out new and capable coaches as skill level improves. Your coach should develop a training system that identifies: next stretch goal, optimal exercises to reach it, the sequence in which skills should be built.

3. Full Attention - must maintain conscious action and full engagement throughout practice period. If you're going through the motions (even with expert guidance) it isn't deliberate practice. Mental fatigue should occur. Sessions are often short and intense.

4. Immediate Feedback - you need feedback from capable coaches to understand what you're doing right and wrong, so that you can modify and correct effort. Over time you'll develop your own mental representations (which can be complemented by recording devices and other tools) to enable feedback via self-monitoring. Ericsson talks at length about the importance of developing and improving mental representations by studying the people who do the thing the best, deconstructing what they’re doing, and mapping it to your own practice.

5. Repetition and Refinement - skills are repeated often but not mindlessly. Each repetition incorporates adjustments based on feedback. The goal is not time spent — it is precision and improvement.

6. Gradual Increase in Challenge - you want to build to expertise in a linear progression, always at the edge of your comfort zone: hard enough to stretch you, not so hard that failure is inevitable. Build layer by layer upon the fundamentals, to let progress compound. You can't afford to go backward and relearn fundamentals.

7. Not enjoyable - since practice occurs at the edge of your comfort zone at a near maximal effort, it is usually not fun while it is happening. It is frustrating and intense. You must be motivated by a desire to improve, not by enjoyment or leisure in the moment.

If a person is willing to train and practice in this way, it almost always correlates with thousands of training hours. Whereas 10,000 hours spent in rote, naïve practice leads rapidly to a plateau, 10,000 hours of deliberate practice makes true mastery possible.

IV. Practicing Deliberately

I practiced basketball deliberately for many years without knowing about the concept — almost always at the edge of my comfort zone, continuously finding that edge by dialing up different variables, employing regular feedback, forming mental representations by studying the greats. I spent several thousand hours of my childhood doing this.3

And this explains how I developed enough skill to play college basketball, as a comparatively small white guy with average athleticism. It also explains how I developed ‘feel’ over time, how I so often accessed flow in game-like situations, and how I can still make 88% of my free throws after not shooting a ball for ten years.

I originally became interested in deliberate practice because I hoped that it could help me develop that basketball-like feel in other areas of my life: while building a business, strength training, skiing, writing, mountain biking, learning a language, and developing other new skills.

Because it is so exhausting, I do think it should be selectively applied, but now that I’ve been integrating it, it feels a cheat code for skill development. It’s hard as hell, but it works. Here is a recent example:

How do you develop feel when you’re building a business? It’s not super straightforward because building a business is so many different things — and the progression of expertise isn’t as clear as it is with something like piano. But it’s the thing I spend the most time on, so I’ve been determined to layer-in deliberate practice wherever possible.

In my experience, the thing to do is to jam the principles of deliberate practice into the ‘most important project’ at any given time. I spend at least four hours each day working on my ‘most important project’.

Right now the most important project is fundraising. At my last business, my ‘practice’ and approach to fundraising was naïve and rote, and my results were middling. I wasn’t particularly good at it, and I didn’t like it. That business made it very far, but eventually it ran out of money. I promised myself I would never let that happen again, and to honor that promise, I recognized that I’d have to become great at fundraising. So I began employing deliberate practice on a more compressed time scale.

Recently, after I put my pitch deck through several rounds of critical feedback, I developed a 10-day sprint for mastering the pitch. I started by breaking the deck up into three sections (four slides each), and I spent an hour on each of the twelve slides over the course of three days, mastering and refining the pitch in manageable chunks.

Then I began pitching the whole thing together, first with notes, then without notes.

Once I mastered the whole thing, I compressed the pitch time from 28 minutes to 13 minutes. Then I began setting an alarm to go off at random times as I pitched. Then I searched for the most annoying and distracting podcast I could find, and played it at full volume while I pitched.4 Then I combined the random alarms and the podcast. Then I practiced visualizing the slides while making the pitch with my eyes closed. Then I pitched a few peers and gathered feedback and made adjustments. Then I made several versions of the deck where I randomized the slide order, and began pitching it out of sequence, with the heavy metal and an extremely annoying podcast playing simultaneously in the background. As a final test, I practiced the pitch with a MrBeast video playing on my screen, instead of slide deck.5

Each time I practiced the pitch, I wasn’t merely focused on maintaining composure and clarity through the mounting chaos — I also had a goal related to a specific aspect of my delivery: my body-language, vocal contrast and variety, intentional pauses, and facial expressions.

My head literally hurt after each daily session. I didn’t enjoy a single minute of it. But I recorded a pitch at the end of each day, and I did enjoy seeing the difference that ten days of deliberate practice made. It was astonishing.

In ten short days, I developed something resembling feel within a very limited scope. I’m excited to see whether ten, twenty, and thirty years of deliberate practice can transform something that is currently a vision in my head, into an iconic, global brand that makes the best outdoor products in the world. I believe it’s possible and even inevitable, and when it starts to happen I bet it will feel like stepping up to the free throw line.

My wife, Antra, is at her mother’s bedside, exactly forty weeks pregnant, listening to her mother’s favorite music, holding her mother’s hand, sobbing in the fetal position, while her mother draws her final breaths.

I bristle later, when the nurse says “everything happens for a reason.” I haven’t worked out the reason just yet, haven’t found the narrative order in the tragic timing — still haven’t found the right metaphors.

A reassuring story can’t arrange a meeting between my late mother-in-law and my unborn child, but I keep searching for one anyway. It’s like Joan Didion said, “We tell ourselves stories in order to live.”

And sure enough, the metaphors do emerge. And so do the stories.

Around midday on August 3, the clouds burn off. The swell picks up. The birdsong stops for a moment of brief commemoration. The sea shell looks like the sun.

My wife tells me about a conversation she had just before we flew to Australia. She is leaving yoga class the morning before our flight, and a wise-looking, older woman she has never seen before stops her at the door and asks how she is feeling in her pregnancy. Antra falls to pieces and shares that she has just learned that her mother in Australia has received a terminal cancer diagnosis.

The woman puts her hand on my wife’s shoulder, and without pausing she looks her dead in the eyes and says, “Your mother needs you. Your baby needs you. You can do this. Life doesn’t give us more than we can handle.”

I’ve heard my wife share this story five times now.

I

The baby is due tomorrow, it’s midnight and labor has just begun.

Except, it hasn’t.

Prodromal labor has begun. Braxton-Hicks contractions have begun. Part of the real thing, but not determinative. It could still be another week. Or two. My wife promised herself she wouldn’t fall for this. But she just did.

She falls for it because she needs labor to begin. Because if this really is labor, her mother will meet her baby. And if it’s not, she won’t. And two days ago the palliative care doctor did say: “Your mother willed herself beyond her prognosis to meet that baby. I have a strong feeling she’ll make it.”

But it’s not labor.

II

The visiting nurse makes her morning observations, then she meets us in the kitchen. She shares that Ilze has entered the ‘active dying’ stage.

We all knew this was coming. We’ve had a month to prepare for this. Only, nothing can prepare you for this. For the irregular breathing, the occasional gasps, the groans, the involuntary jolts, the hollow temples, the sunken cheeks, the eyes rolled back. It feels so unfair. It is so unfair.

I play it forward: in a few hours my wife won’t have a mother. My children will never meet the person who created their mother, who made their mother so special. Will never know the woman who picked out their first teddy bears and loved them to bits before they were even conceived. I sit beside the bed and I’m stuck in a loop of parallel realities. It feels related to denial. I think: Is it possible that this isn’t actually happening? Couldn’t she just as easily live for another 30 years? She could teach my kids so much. She could still look like she looks in this photograph. Or that photograph from six weeks ago. Healthy, full of life. Surely this is some sort of glitch? Maybe we’re really back in Oregon right now and this is some awful dream? Maybe she’s in Oregon with us, preparing postpartum meals for my wife. Biking along the river at sunset.

My mind keeps playing this trick on me — sometimes it happens in a flash, sometimes it’s drawn out, sometimes I dream it. A day passes in this fugue state. I do another loop and it’s interrupted by a gasp. And I’m back here, and it’s over, and she’s gone.

III

Australian Aboriginals have a belief, I’m told, that when you travel by plane or by car, your soul takes time to catch up with your body because the soul can only move at a walking pace. This causes ‘soul lag.’

I arrived in Australia by plane a month ago from America. Maybe there really is a sundering, because nothing makes sense right now. Perhaps my soul is still traveling somewhere in the Pacific, leaving my mind and body to sort out the essential facts of the current situation.

The facts are these: I’m very far from home, my wife is overdue with our first child, and her mother is dead.

IV

“Don’t kink the hose,” Antra says. “Don’t suppress the feeling. Let the feeling pass through you. The only way out is through.”

She tells me these things. But I’m not about to birth a human. Not the one whose beloved mother is being cremated tomorrow.

How could someone be subjected to this? And how could someone handle this sort of thing with grace, with strength, with poise and eloquence? Without a hint of self-pity?

I’m not sure how. But somehow Antra knows.

Maybe she learned it from her mother.

V

Four days after Ilze has passed away, the cremation and memorial service is scheduled for eleven in the morning on August 7th.

As arrangements are being made, my wife’s father turns to me and says: “I reckon the baby will come on the seventh. We’ll have to cancel the service.”

On August 7th the real contractions begin. The service is cancelled. An hour before the service is scheduled, the baby arrives.

Later I ask him how he knew about the seventh.

“I just had a strong feeling,” he says. “Ilze was waiting for the baby. The baby had to come before the cremation.”

VI

A few weeks ago, some of Antra’s closest friends from different parts of the world organized a mother’s blessing to usher in her motherhood. The ceremony was planned before her mother became sick, and now it has assumed a special poignancy because Antra is zooming in from an oncology ward in Australia, being celebrated for her impending motherhood alongside her own dying mother.

As the ritual unfolds, a yellow, beeswax pillar candle burns beside each of the women and the ceremony concludes with a mantra-like song:

We all come from the mother, and to her we shall return, like a drop of rain, flowing to the ocean

Antra and her mother find comfort and connectedness in the cyclicality of these words. It commemorates Ilze’s profound, lifelong connection with the ocean. In her final days, Ilze and Antra draw strength from the message and they sing it together. And when Ilze passes away and the mortician comes to collect her body, Antra and I visit the ocean.

When we arrive, we’re greeted by a huge swell and a rising tide. The waves form further out toward the horizon than in the days before. They roll in ceaselessly, rise higher, fall heavier. The waves thunder down relentlessly — crashing into a mercurial mist, which glows silver on the pastel twilight.

We walk along the shore and Antra asks me to find a shell for her mother. I find one and I show it to her.

“Yes. That’s the one,” she says, “It looks like the sun.”

“It does.”

I pick up another shell, similar in size and shape, and another smaller one. I say: “This one is for you. And this one is for the baby.” She smiles and nods and takes the shells.

She looks out into the ocean and she sings. Softly and self-consciously at first, then louder and louder over the booming waves, she sings until she can no longer sing from soreness and sadness.

We all come from the mother, and to her we shall return, like a drop of rain, flowing to the ocean

In the evening, I enter our bedroom after the sun has set. It’s dark out and the shades are drawn and the single source of light comes from an altar at the center of the room — the beeswax pillar candle from the mother’s blessing sits upon a coffee table, and below the candle lay three sea shells that look like the sun. Antra is kneeling before the candle and staring into the light and sobbing from the deepest, darkest place she has ever known. Candlelight flickers radiantly across her tear-soaked face. Her shirt is dripping wet from crying.

She gasps. I wipe her face dry and all she can say is, “I’m just so sad.” I calm her and hold her and we go to sleep.

On the second night after her mother’s death, it’s the same.

On the third night it’s the same too, except I wake a few hours later to the strike and sizzle of a match — to the beginning of a different kind of ceremony.

It’s morning but it’s dark and it will be dark for many more hours. Antra lights the candle, re-aligns the seashells with her middle finger, kneels and breathes deeply. Her eyes are closed and she isn’t crying. She breathes with ritualistic serenity.

She shudders and shivers. I look over from the bed. There are goosebumps on her arms. I walk over to her and put a blanket over her shoulders and I put my hand on her back and a wave of contractions ripples through her body. Then it’s over and she breathes again.

Five minutes of focused calm, one minute of rippling. Four minutes off, one minute on. Three minutes, one minute, three, one, three, one.

The contractions intensify. She sits in front of her candle and her shells, she breathes, groans, breathes.

The contractions intensify. The contractions roll in from the horizon like waves, rising high, falling heavy, falling heavier. Rolling rhythmically and ceaselessly for hours. Waves, thundering down relentlessly, finally erupting into an unimaginably savage and sublime thing.

I steady my shaking hands under a tiny human head and then another primal push and then I’m holding a whole baby body. A baby boy.

The pillar candle casts a warm, reassuring glow onto the boy as he searches for air. He finds it, he gasps.

I hand Antra the child and she brings him to her chest. She is stunned by a warmth and joy unlike any she has ever known, she turns to the boy breathlessly and says, “My god. It’s Emil.”

The circle closes. The blinds are raised, the candle is snuffed.

We all come from the mother, and to her we shall return, like a drop of rain, flowing to the ocean.

Last year I wrote about a study which forced me to reconsider my relationship with pain. The upshot is that roughly 70% of men would rather painfully shock themselves than sit quietly in an empty room for a few minutes.1 We default to painful action over patient contemplation.

Before I read that study and wrote that essay, I was about to start an outdoor gear and apparel business. But through the process of writing I had come to see this business as a kind of ‘pain button’ — a way of shocking myself to feel and do something, a way of avoiding deeper questions about what I really wanted.

To people who were less familiar with the outdoor industry, I would describe the business that I was planning to start as the ‘next Patagonia.’ This was shorthand for ‘an outdoor company, but an ambitious one.’ Specifically, I was planning on starting an ultralight backpacking company. That was the business I slowly backed away from last year, and it is the same business I just officially incorporated. The products are in development, the brand identity is nearly finished, and every day I get a bit closer to launching it. It will be called Ansel.

In moving forward with the business, I knew I’d be answerable to my earlier writing. After all of the thought and introspection that went into writing an essay about self-inflicted wounds — was I really about to aim at my foot and fire? Or was it suddenly a good idea? What had I learned or done over the past six months that changed my mind?

There is a short answer and a long answer.

The short answer is that last November I began dreaming about the idea regularly, and for a whole week straight the dreams energized me so much that they would wake me at around 3 AM. Then, I would lie in bed for hours at a time because of some product idea, some minor brand detail, some marketing concept. Over a period of more than two years I simply couldn’t quit the idea. I tried every way I knew how: intellectualization, interrogation, public accountability, neglect, competition, jury trial. Finally, after so many backs and forths, I concluded that it would be more painful not to start the business, than to start it.

It was easy to imagine myself at age 80, sitting on a porch with my best years behind me, regretting that it was too late to build the thing I really wanted to build.

Fortunately, I’d given myself this out in my original essay:

“...the deeper you explore the purgatory of existential personal inquiry—the unknown—the better your chances of discovering the things that are worth suffering for. A family, a relationship, a business idea.”

Some things are worth suffering for. And after taking a long, hard look at myself, I decided this was one of those things.

But there is also the longer, more complicated answer. I spent a ridiculous amount of time trying to figure out how to figure out what to do with the rest of my life, and I figured it out. So I thought I’d share an abridged version of how this played out.

The Problem with Problem Selection

After writing The Pain Button I began to wonder how smart and successful people made decisions about the problems they chose to work on professionally. As I searched for answers, it became clear that there really weren’t answers. In fact, the most interesting thing I found was a Stanford research paper which revealed that PhD candidates spend 1-2 weeks deciding what they’ll spend 100-250 weeks researching. In other words: they spend one week planning for every two years they spend working. The conclusion of the paper was that very smart people are very bad at making decisions about what to work on.

Abraham Lincoln’s famous adage came to mind: “If I had six hours to chop down a tree, I'd spend four sharpening the axe.” His planning to doing ratio was 2:1. I became determined to develop a process that would lead me to a clear, rational answer — no matter how long it took. I couldn’t stand the thought of giving so much of my remaining life force over to the wrong thing.

Eventually, I developed a five step process that I felt good about, and my process led to more than a hundred ideas that I spent time contemplating, researching, refining, and in some cases even soft-pitching to venture capitalists. But I would inevitably re-encounter the same problem: I would get an idea to ‘pencil’, then I would pause for just long enough to imagine what it might feel like to turn that idea into a company — a company that made fashionable air purifying respirators, or software that improved the employee reference process, or hardware that helped enforce school phone bans — and I just couldn’t imagine myself springing out of bed in the morning to work on it.

The ideas were failing some sort of autonomic passion-gut-check-test. So I moved ‘passion’ to the front of the process, and that short-circuited everything. I began generating ideas and shutting them down almost instantaneously. Something about passion and the cold rationality of the process were irreconcilable.

I went back to the drawing board.

Infinite Pain

As I considered where and why things were breaking down, I began to see my clinical process as an over-corrective response to the ‘Pain Button’ study. That is to say, I knew I had a high pain tolerance, so I was trying to avoid walking into a pain trap. I was looking for a business that would be the least painful to build and operate, and the most financially rewarding per unit of pain.

Meanwhile, as I was busy building my problem selection process, I was also devouring dozens of biographies about history’s greatest entrepreneurs. And I was beginning to recognize an incontrovertible pattern: entrepreneurship is pain and difficulty. There are no exceptions, there are only different ways of tricking yourself into enduring the pain.

While there may be a continuum of pain along the business idea spectrum, I came to see that anyone who believes that their fledgeling business concept will be pain-free is either inexperienced or delusional. In a startling amount of cases, if the entrepreneur knew beforehand exactly how hard things were going to be, they wouldn’t have started. The founder of Nvidia, which is currently the largest and most important company in the world, said exactly this:

I wouldn’t [have started Nvidia]. Building a company and building Nvidia turned out to be a million times harder than any of us expected it to be. And at that time, if we realized the pain and suffering and just how vulnerable you’re going to feel and the challenges you’re going to endure and the embarrassment and the shame and the list of all of the things that go wrong… I don’t think anybody would start a company. Nobody in their right mind would do it… I think it’s too much. It is just too much.

I encountered some version of this sentiment so many times that it seemed crazy not to pay attention. It also felt like something I could have said myself about my previous business experience.

The only option for avoiding the pain involved in building a company was to walk away from the game. But it is the game I have long felt born to play, and my compulsion to play has always felt deeply intrinsic. So I started thinking about the games within the game. Even if the pain was inevitable, surely there was an ideal way to pick the right problem to solve?

Everything (in my life) clicked into place when I encountered the concept of ‘infinite games.’

Infinite games are games played for the purpose of continuing to play. Finite games, on the other hand, are played for the purpose of winning (chess, soccer, war). This concept and dichotomy was laid out by James P. Carse, in his 1986 book about ‘life as play and possibility.’ It resonated profoundly with what I believe to be true about daily-meaning making — about life as play. But until now, the missing link in my life had always been an authentic sense of ‘professional play.’

Most people, especially hard-charging business-people, view work, parenting, hobbies, fitness, and relationships as finite games — as contests to be won — but when the game becomes the end itself, your objective is to keep playing for as long as possible. And when this is your objective, you become untethered to moving goal posts or external validation, and you get in touch with why you’re really playing in the first place. And why it’s fun to be a human. You become more creative, more resilient, and more fulfilled. You become a child. You can’t get enough.

If you’re interested, like me, in starting a consumer products business: you notice when infinite games are chartered into a business’s raison d’être — just as you can recognize the exact moment when they no longer are.2 The founders with product and brand legacies that impress me most are the ones who play infinite games.3 The privilege of creating great products, for them, is its own reward.

And the interesting thing is that when you play infinite games and you’re truly obsessed with what you get to work on everyday, you end up playing the game for a very long time, which means you invoke one of the most powerful forces in the world: the law of compounding. Your investment of time, energy, and attention, aren’t scattered, and over time, this non-diversified intensity ends up accumulating into something huge. You have more resources to do the thing you love the most — and you get to make it even better.

It turns out that the simplest heuristic for a ‘problem selection process’ is not five-parted, it’s not clinical, and it’s not particularly rational. It’s very simple: what wakes you up at night, in a good way? Would you want to work on that thing for the next 50 years, even if you knew it would be insanely painful and difficult?

If something comes immediately to mind, get started and don’t stop.

A few weeks ago my wife, Antra, put her father on speakerphone as we were getting into bed. Her father is a stoic man. He had called twice and now his voice wasn’t exactly steady. A few days earlier, Antra’s mother, Ilze, had seen a doctor about a migraine, and in the tests that followed they traced the migraine to a cancerous growth near her gallbladder.

After a week in the hospital — after half a dozen additional tests and the coordinated assessment of seven specialists — a veteran doctor sat beside her hospital bed and he cried as he shared the diagnosis. She had an unlocatable, untreatable, and aggressively metastatic cancer growing in her stomach. His prognosis: 6 months at most, with a generic chemo.

A week earlier — a day before the migraines — Ilze had gone for a long bike ride before packing her bags for a trip to America. She’d planned an extended visit to care for my wife and our soon-to-arrive baby, and she packed gifts, toys, and clothes that she had been collecting for years, for this moment. The due date was in four weeks. And now she was in the inpatient ward in the Australian capital, wondering if she’d live to hold her first grandchild.

Two days after the prognosis, Antra and I flew to Australia for the indefinite future. We left on the longest day of summer, and we were greeted forebodingly by the winter solstice. Within an hour of our arrival at the hospital the head oncologist visited and shared that he no longer recommended chemo given the rate of metastasis and the ‘tempo’ of advancing symptoms. He did not cry, but he seemed to find it very difficult to say what he had come to say, and so there were times when we had to ask him to speak more plainly. In the end, what he said was that Ilze had ‘short weeks’ to live — and that there was a low probability of her meeting our child.

I’ve now spent a few weeks at the foot of my mother-in-law’s deathbed, and I’ve watched my pregnant wife become a mother to her mother. I’ve watched her nurture, cook for, spoon feed, massage, serenade, cuddle, shower, and love her mother beyond belief, from dawn until dusk. The daily vignettes are unimaginably beautiful and painful, so raw and gut-wrenchingly poetic that they split you right open. My wife, the daughter, grows life in her womb, a life-force that kicks so powerfully that it is often visible from across the room — while her mother’s body grows the thing that will bring death. The two paths moving involuntarily, seem increasingly destined to miss each other.

Our days here are slow. Much too slow to count for anything in today’s world — but unlike some entire years, each day here is marked by quiet, life-altering moments of introspection, reflection, and conversation. As life and death march inexorably forward, there is no question about what lays ahead for us, and so we speak openly about it and we compress a year’s worth of storytelling and vulnerability and gratitude into a few waking hours. We open the safe and hear the story of Babuņa’s mink shawl and her amethyst jewelry set — smuggled out of Latvia on the eve of Soviet occupation. We hear about the magic rock that fell through the sun roof in the Outback, and the wonky clay horse whistle in the kitchen. We learn about the history and utility of Baltic amber — the 44-million-year-old, fossilized tree resin, prized for its purity — and we pick through an incomparable collection of amber relics.

We discover what it means to be connected to something deeply ancestral: we document a family history, and absorb a compressed postdoc in Latvian symbology, jewelry, and culture. Ilze has been described as the ‘guardian’ of Latvian traditions, rituals, and knowledge — a virtuosic silversmith, an award-winning teacher, a cultural historian. With every new revelation we mourn what we’re losing, and we scramble to preserve what we can — making voice memos, filling notepads.

It’s an unspeakably sad and tragic paradox — to watch someone you love become a mother and lose a mother within a matter of days. It’s a duality nobody deserves to face. Between breaks in caretaking and conversation, a deep cosmic unfairness sets in. Especially as the pain, fatigue, and nausea advance. The only way I can make it make sense is to find the beauty in all of it. As difficult as the situation is — and perhaps because of how difficult it is — the beauty is always close at hand.

Something beautiful happens when the end of something you love looms in the periphery. When there is an imminence and inevitability about it. When the end is ‘short weeks’ and not years away. The days don’t feel longer, but each day and each moment feels precious and sacred in a way I’ve never known before. Given even a few weeks' notice, the death of something or someone special becomes a prism for so much of what matters and has mattered in a life. All that was original and irreplaceable and sublime in a person — you see it with astonishing clarity and you absorb its final essence. An urgent intentionality envelops you, and preserves memories and moments like the ghosts of history frozen in amber.

Bryan Johnson is aging at a rate of 0.76 years per year. This means that his ‘biological age’ increases by 277 days for every 365 ‘chronological days’ that he lives. His health and longevity protocols cost him two million dollars per year.

You may already know this because Bryan Johnson’s quest to live forever has earned him appearances on the world’s biggest podcasts, profiles in the world’s biggest magazines, and his very own documentary on Netflix. Where his desire not to die was once reported with sneering, satirical derision, it is now explored with self-interested curiosity by a popular culture that seems increasingly to share his obsession with the possibility of age reversal. Last year, one of the top selling books in America was about metabolic health. The year before, it was Outlive: The Science and Art of Longevity. Perennially now, one of the most followed and shared podcasts in the world is the densely scientific and longevity-focused Huberman Lab, which espouses healthspan ‘protocols’ for ‘dopamine management’ and ‘circadian hygiene.’

In this cultural context, Bryan Johnson is in the process of becoming a household name. With his upright posture, and his milky, wrinkle-free skin, and his flat stare—Johnson now mixes with the Kardashians, now offers a pale and uncanny alternative to the notion of beauty that Kim and Khloé popularized over the past decade. A lot has been written and said about the man and his quest, but one thing that I have not yet heard anyone mention is that there is actually a way to age at half his pace for one-percent of the price.

Over the past three years—a period during which Johnson has ‘aged’ only two and a quarter years—I lived for about eight years. Or something like that. Perhaps even more. Perhaps much more.

This is a not totally scientific claim, but let me show you what I mean.

Over the past three years I: married the love of my life and threw a three day off-grid wedding festival in the Sierra Nevada backcountry with 120 of my closest people. I cycled with my wife for six months across nine countries in Europe, circuitously, along country roads, camping out of panniers, noticing hundreds of discrete things per day, discussing them and writing about them and solidifying them into long-term memories. I moved to a new city, made new friends, and remodeled a century-old mill house—learning to drywall, tile, paint, demo, and refinish floors. I read more than 50 paperback books, beside streams and rivers and under groves of Ponderosa Pine. I rafted under the towering red walls of the Grand Canyon with my best friends, and among wild wolves in the Alaskan wilderness, and through the white water and ice floes of a Grizzly Preserve in the deepest reaches of the Yukon Territory. I hiked 15,000 vertical feet around Mount Rainier, and I meditated for ten hours per day, over ten consecutive days, in the shadow of Mount Saint Helens, without reading, writing, or speaking a single word. I made detailed comparisons of single-origin espresso at fifteen of the finest Melbournian cafes. I spent two weeks staying with strangers and eating out of roadside farm stands and bicycling across four states in New England during peak autumn, under the luminescent glow of fall foliage. I experienced full winters’ worth of backcountry ski outings, cross-country ski marathons, and powder-filled first runs at alpine ski resorts in the Northern Cascades and the Canadian Rockies. I incorporated my dream company, built a brand, and began developing our first full line of technical outdoor products. I spent months immersed in the euphoria and sorrow of life and death: I welcomed my first child and stood by in grief as my wife lost her mother, both within a week, in the same home by the Australian sea.

All of this, interpolated by long, late dinners with cherished friends and family, full of stimulating conversations and skin-contact wine. All of this, and frankly much, much more.

Compare the multitude of experiences above to Johnson’s daily calendar flipping routine, in which one day mirrors the next with a sameness that doesn’t merely flirt with but seems to strive for the obsessive compulsive. A daily rhythm that begins at 4:30AM and ends, incontrovertibly, alone in bed by 8:30PM. A rhythm that consists of daily body composition measurements, standardized indoor workouts,1 and a two hour evening procedure consisting of skin care, dental care, and ‘relaxation time.’

Compare the handmade pasta dishes my wife and I ate while bicycling across Italy, the liver patés in Denmark, the pickled herring in Latvia, the beef heart stew in Oregon, and the slices of pizza in Naples and Brooklyn—compare the depth of the associations and memories created by these culinary experiences, to Bryan Johnson’s diet across those two years: a daily ordeal consisting of the same exact thing, always 1,977 calories, always a pomegranate pudding in the morning, always broccoli and lentils in the early-afternoon (sometimes blended), always supplemented by powderized nutrients and always complemented by an AM dosage of more than 100 pills. All of this, consumed by a daily dinnertime of 11 o’clock. In the morning.

In considering our contrasting approach to life, it seems to me that there are two ways to think about increasing one’s lifespan: the first is to slow down the body clock—to decrease the amount of biological aging that occurs in chronological time by pursuing risk mitigation and health measurement efforts to their extreme limits. And the second is to dilate time—to increase the amount of perceived time that occurs as time passes chronologically, by increasing the amount of memorable experience that occurs over a given period of time. I call this ‘experiential time.’

The modern anti-aging and longevity movement embraces the former approach, and Johnson has been its foremost pioneer and poster child. At great expense, he is in the process of extending his life by aging more slowly—25% more slowly than a normal person. The major trade off is that the further down this continuum you go, the more you must replace experiences with clinical routines and scientific structure. This Groundhog Day-like existence results in far fewer memorable experiences per calendar year, and when there are far fewer memorable experiences for the brain to process, the perception of time contracts. In other words: time passes more quickly. In a best case scenario, someone pursuing longevity through perfectly-dosed monotony will live a much longer life than the average person, while feeling like he lived a very short one.

My approach to living longer is to increase perceived lifespan by living 2.5 years worth of ‘experiential time’ per year. I believe that the best, cheapest, and most thrilling way to live for 200 years is to do it in 80 or 90 experientially rich years, rather than in 400 experientially hollow years.

Of course, the knee-jerk protest is that I’m just making stuff up—that what I’m proposing is subjective and arbitrary and unscientific—that there is no such thing as ‘experiential time’ or ‘experiential age.’ But maybe there should be, and in fact, maybe we already intuitively know that there is.

We know, for example, that ‘experiencing’ more in life isn’t merely fulfilling; it also leads to the feeling of having lived longer. Research has repeatedly shown that the perception of time stretches when the brain processes more details and emotions—and that rich and rewarding experiences feel longer in the moment and in retrospect than monotonous ones. This perceptual phenomenon is so well-studied and validated that it has its own coinage: the ‘oddball effect.’2 It also corroborates research which shows that as people age they report feeling that time passes more quickly. The widely accepted explanation for this is that the number of novel experiences typically decreases as one ages, which means that the brain has less new, rich, and meaningful stimuli to process.

Finally, it has been shown through studies on attention and ‘temporal estimation’ that when subjects are fully engaged in a meaningful task, they overestimate the amount of time that has passed. In other words: when people are working on interesting and stimulating things, they become absorbed in the work and they tend to perceive time as having stretched.

Isn’t it fair to say, then, that a life lived in ongoing contact with new stimuli and rich, challenging, meaningful experiences will feel longer? And if a life legitimately feels longer, how much different is that than a long life that feels short. Again, which is more appealing?

‘Experiential time’ is far from far fetched. It’s the concept that explains why all time is not created equal. Explains why just about anyone would trade twenty-eight safe, ordinary, routine-filled days, for seven days of exploration, in a new country with a best friend. It’s the term that explains why we’d readily trade some of our time at 4 to 1. At 10 to 1. And when considering our very-best memories, maybe even at more than 100 to 1.

What we should want is to be experientially old, not biologically young. There is a way to harmonize the two without becoming deranged by the constant measurement and management of biomarkers, without resorting to a transhuman diet, or an antisocial sleep schedule, or a fear of dying. The way we currently think about longevity mostly misses the forest for the trees. It measures age based primarily on ‘biological time’—on relative organ and ‘biomarker’ health—a proxy for expected lifespan, which can’t even guarantee a longer life.3 ‘Experiential age,’ on the other hand, can guarantee the perception of having lived for longer, through a rich abundance of memories and impressions.

What I’m getting at is fundamentally about a more considered weighting of quality and quantity.

What is the point, after all, of desiring a long life? The thing to want is a good life. And so the thing to do is to be reasonably, but not obsessively, concerned about your health, and to optimize for ‘experiential age.’

The way to optimize for experiential age is to pay closer attention to everything. To stop scrolling so much and stop worrying so much and stop planning and empire-building so much, and to start going on walks around your neighborhood and start noticing things that were always there that you never noticed before. You begin noticing more things, big things and small things, then you begin contemplating those things with childlike awe—you take photos of them, or draw pictures of them, or write about them. And you talk about them with other people. And you keep expanding this circle of noticing—beyond your neighborhood into the next neighborhood over. Into the next state over. Into other countries, other continents.

Every day, we can compress time by letting the day pass unremarkably, unmemorably; and every day, even during the busiest or boringest days of our lives, there are an infinite number of things to notice, and there is an opportunity to expand the perception of time by noticing and contemplating those things.

You can get more years in your life by living like Bryan Johnson, in a food-is-fuel, sleep-is-job-number-one, risk-mitigation vacuum—or you can get more life in your years by deeply immersing your attention in the world around you, and by pursuing interesting and rich life experiences. Either way you’ll end up in a similar place perceptually. And, in spite of his objective and his war chest, it is my prediction that eventually Johnson will die. And when his quest comes to an end his biological age will be irrelevant, and his chronological age might look impressive on a tombstone, but his experiential age is the thing that he will be contemplating as he takes his final breaths—and like everyone else in that moment, it is the thing he will wish he had more of.

Thanks to Michael Dean for feedback on this essay.

1

A few years ago my business collapsed and a quarter-life crisis ensued. In the anguish and self-inquiry that followed, I arrived at a kindergarten-grade epiphany about life and purpose: What I want in life… is to have a good life. I want to flourish.

Then came the obvious question: What does it take to flourish? After several more months with a journal before me and a ballpoint in hand, I had it figured out. Or something like that. I had: a hierarchical list of ten personal values whittled down from forty quarterfinalists, a loose sketch of principles for life and work, and a sprawling list of hobbies and interests. I considered how I might take this apparent roadmap and cram it into a life of flourishing. I was overbooked. I couldn’t imagine keeping track of it all. 

Out of all of the values and principles and the heaps of ambition, I wondered where the real leverage was. In trying to design a good life, was it better to home in on even fewer values? Select fewer principles and fewer hobbies? How could I flourish in the fewest possible moves? More contemplation and compression followed, and the resulting conclusion was that ‘a good life’ comes almost entirely down to working through and answering three questions as assiduously and thoughtfully as possible. Three questions which result in three decisions that rub off on nearly every other important decision in life—for good or for bad—through second- and third-order effects:

1. Who should I spend my life with?

2. Where should I spend my life?

3. What should I spend my time on?

Though each question can be explored along several dimensions,¹ it is the primary dimension that matters most by an order of magnitude. The primary dimensions of these questions are: Who should I marry? Where should I live? What should I do for work? The more time I spent considering the nature and implications of these questions, the more urgent and underrated the questions seemed. You get all three right, you flourish. You get any of them wrong and you’re swimming up current, big time.

There is something almost patronizingly obvious (or perhaps satirical seeming) about pointing out the importance of who you marry, where you live, and what you do. But it must not be so obvious, because the answers to these questions are often taken for granted or left to chance. And we were never taught how to address and explore them in school. And nobody ever told me: you don’t need to worry about much in life, just focus on getting these three things right and keeping them right and you’ll be fine. As a consequence, few of us thoughtfully prioritize finding a truly compatible partner (or seeking to understand how to be a wonderful partner for another); very few of us spend a few months, let alone a whole year, deliberately choosing where we’ll spend our lives; and very many of us fall into a career and then build a life around it, rather than the other way around. 

I’ve already shared some thoughts related to the question of what, and I’ve spent the past few months developing an extensive ‘problem selection’ process to tease out the question further. I plan to cover different aspects of the question of who in an essay soon. Here, I’ll examine the question of where. 

“Where should I spend my life?” It is a question most often addressed indirectly. The most common answers to the question seem to be: where I grew up, anywhere but where I grew up, where my partner grew up, where I went to school, where I took a job, I heard Austin is cool. It is quite often a decision one cannot recall ever having specifically made, or a decision that was made long ago under circumstances that barely resemble current ones. It is rarely a decision made after considering, researching, visiting, and deliberately trialing several viable contenders—after contemplating how different places intersect with hobbies, interests, needs, desires, ambitions, and hopes. So, while most people would agree that where you live really matters, most people also assume that where they live is good enough, and that good enough truly is good enough.

Or, perhaps the thought just never occurs to most people—the thought of saving up, then carving out a block of one’s life to intentionally decide where to live. But why shouldn’t it? Yolo, right? How many things affect the quality of your life more than the place you live?2 Would more people spend more time on this problem of place, if they had been instructed how to choose wisely, or if they believed it was possible to truly choose? Because if it’s a top priority it’s almost always possible to choose, and it really can be done for roughly the same cost as staying in one place. And it is totally worthwhile, even if you end up back where you started.

Where you live does matter. You can live in a place where you don’t lock your doors when you leave, or a place where you are unfailingly conditioned to use knob locks, chain locks, and deadbolts. You can have access to beautiful, remote, open natural spaces within minutes or within hours or within half a day’s drive of where you live. You can live in an echo chamber, or you can live in a cultural hotbed, or you can live in something in-between. You can live in a place that adds financial pressure to your life, or relieves it. You can live in a food desert, or in a place where fresh produce is abundant and small-scale farming is supported. You can live where neighbors have block parties, or you can live in solitude. You can live within walking, driving, or flying distance of the family and friends who matter most to you. You can live in a place that makes you feel like a place doesn’t really impact your overall well-being, or you can live in a place where you pinch yourself everyday, because you can’t believe you get to live in that place. Countless choices create infinite possible futures. Your environment shapes you completely, and when you live in a place that fuels you, rather than a place that slowly, imperceptibly drains you, you become more alive. 

And yet, it’s common never to fully perceive this or own the opportunity to explore the question: where should I set up my life?

I’ve thought about where a lot over the past few years. When I began contemplating the three questions and taking them very seriously, the biggest gap of the three in my life was the matter of place. I lived in Los Angeles, which was great for so many things and great in so many ways—but it was hours from the remote alpine meadows and streams and air that made me feel the most alive. My wife felt the same way. So we began researching cities and towns and regions and even countries, looking for places that met a criteria that aligned with our values and interests and the vision we were developing for our life. We narrowed it down to fifteen contenders ranging from big cities to small towns,3 then spent seven months driving across eight states, immersing ourselves in each place. At every stage, in every place, we considered trade-offs and we imagined different possible lives. We narrowed it down to three finalists, then returned to each of those finalists for roughly two months. Then we selected a home. Bend, Oregon. Now we live there, and everyday we both say something like: I can’t believe how great it is here.

Before I began searching for a new home, I had spent far more time comparing online reviews of $20 products than I had spent comparing cities where I could live a good life. Growing up, my Dad called this ‘majoring in minors’—a miscalculation of priorities. But nobody ever mentioned ‘majoring in majors,’ and nobody mentioned what the real ‘majors’ even were. 

The real majors are: who, where, and what. Out of the millions of decisions that one makes in a lifetime, there are many that don’t matter and quite a few that do, but there are just three major decisions that count for almost everything: who you spend your life with, where you spend it, and what you do with your time. Each of these three areas of your life should be given an excruciating amount of consideration—as though they’re the only three decisions you’ll ever get to make, because in some indirect sense, they are.

Note: I recognize that a common objection to the ideas above is that the ability to decide these things is inherently privileged. Particularly the idea that anyone can have complete control over where they live and what they do. I will readily admit that there are all kinds of exceptions, but by and large I respectfully disagree. I think that most people can find a way to initiate the things they truly want in life. Actions express priorities. And the inertia that causes people to describe things as impossible is often really just fear: of the unknown, of disruption, of instability.

Thanks to Michael Dean and for feedback on this essay.

The other day, I arrived at my co-working studio and found that my favorite desk was taken. The perpetrator had left behind a collection of personal belongings, and as I scanned the desk my attention stopped on something left behind: a cell phone, abandoned and impotent, imprisoned inside of a clear, acrylic lockbox with a countdown timer. I recognized the box at once: the KSafe, “America’s #1 Habit Breaker.”

I knew all about the KSafe because there isn’t a focus-related quick fix between Bend, Oregon and Bangladesh that I haven’t used or contemplated using, and I also knew that this person was dealing with a habit that a lockbox had no business promising it could break. 

Though mostly futile, these kinds of focus Band-Aids make good business and they’re the solution most commonly deployed upon our wandering attention. Stop-gap solutions like: Red Bull, AdBlock, Forest, Freedom, Self Control, Focusmate, nootropics, lion’s mane, Brain.fm, Instapaper, Mailman, Screen Time, greyscale, etc. etc. et. al. If I listed them all, I’d break the Substack word count limit. Focus aids can be helpful when they play a support role in your effort to concentrate, but even with an entire bandolier at your disposal, you’re still walking into a wildfire with a water pistol.

You can blast your brain with stimulants and hide from your phone all day long, but you can’t hide from yourself. You can’t hide from your mind. And the mind is where your attention breaks down, or doesn’t. So you need to learn a few things about how it works, and then you need to train it to work more effectively.

About four months ago, I was the kind of person who might resort to Ksafe Matryoshka: placing my phone inside of one Ksafe before nesting it into another one, then into another Ksafe, and so on. My attention span had tumbled to its nadir and I was willing to try anything. 

So I did try anything, and everything. And after much trial and error, I became the type of person you have to hover above and repeat the name of three times to arouse from an intense and singular attentiveness. I became undistractable. The first big unlock for me was when I learned how attention actually works. 

Previously, I thought about attention as getting “locked in” or “being in the zone.” I thought it was one thing. It turns out that it’s something more like three things, three cognitive-clusters—like a three-parted network within the brain, where each part performs a distinct and familiar function. The names of these clusters are the:

1. Orienting system aka flashlight

2. Prioritizing system aka prioritizer

3. Alerting system aka lighthouse

The orienting system is pretty close to what I used to imagine attention was entirely about; it refers to the tunneling type of concentration that we associate with being “locked in” on something. Think of this system as your flashlight. When you point your flashlight at something, you create a beam of light, and that narrow circumference of light is surrounded by an infinite expanse of dark. The light stuff is the field of view in your mind’s eye, it’s what you’re focused on; the dark stuff is everything else that you no longer notice. 

You have a limited amount of attentional space, and when you’re super focused on something your flashlight uses up all of that space. Your flashlight can be directed inwardly (e.g. reflection, rumination, imagination) as well as outwardly (e.g. a book, a TikTok video, your dog); and it can bend time: you can shine it on the thing before you in the present moment, you can shine it into a memory of the past, and you can shine it imaginatively onto the future.

If you have perfect powers of concentration, you can shine your flashlight exactly where you want, exactly when you want, and you can hold it there until your higher self says: “Times up! Great work reading Infinite Jest for 30 minutes without thinking about anything else. We’re done here.” Then you move on to the next most important thing, and you shine your flashlight on that next thing. 

Unfortunately, you don’t have perfect powers of concentration. Your flashlight operates on some continuum of unreliability, because your higher self has been utterly annihilated by things like sugar and modern technology and anomie. Year by year, your higher self is atrophying: instead of holding steady on that one thing you decided you wanted to focus on, it is relentlessly jerked around throughout the day by notifications, distractions, undefined priorities, inner urges, interruptions, and more. The average length of time that a person now holds his/her attention in one place is 47 seconds.¹

This so-called higher self is calling very important shots, and it keeps getting hornswoggled into trivial matters—but, what exactly is it? You can think of the higher self as a triage machine in your brain’s prefrontal cortex. Attention researchers call it the central executive, essentially your brain’s CEO, but this is oddly inconsistent with the rest of their vocabulary so we’re going to call it the prioritizing system, for short: the prioritizer. Your prioritizer is the attentional brain within your brain, it’s the traffic controller that facilitates handoffs of attention. It decides what to point the flashlight at based on your goals, safety, desires, urges, etc. If you don’t have a clearly defined priority and a clearly structured set of boundaries, your prioritizer will be forced to negotiate between a pluralization of competing options, pretty much all the time—every red-bubble, ding, urge, and inner impulse presenting yet another option to consider.

We’re not done with the prioritizer yet, but before we go any further it’s important to understand the role of the last system of attention: your alerting system. Your alerting system is linked to your survival instinct. It has been fine-tuned over the centuries to anticipate and react to environmental threats, and it’s easiest to think of it like a lighthouse—as your diffusive attentional awareness. Your lighthouse scans the periphery broadly, focusing on everything generally, and focusing on nothing specifically. This is the part of your attentional system that picks up background noise and passes it along to the prioritizer, which must then decide whether that information is worthy of redirecting your attentional flashlight towards and taking a closer look at. If you’re in a super stimulating environment like an airport, your alerting system is going to be absorbing all sorts of colorful and potentially important information—beeps, buzzes, juicy eavesdropping fodder, awkward families doing awkward things, the creepy guy next to you in a Slipknot shirt with wired headphones watching YouTube Shorts on his phone and loudly slurping a Mountain Dew, flight attendants apologizing or not apologizing about delays and saying names and flight numbers into a PA system—your lighthouse picks up all of this stimuli (and so much more) and passes it along to your prioritizer for processing, while you’re sitting there trying to point your flashlight at a book. Here are some ways this could play out:

• Bad: Your lighthouse dutifully shares all these stimuli with your prioritizer, and your prioritizer is dysfunctional and basically useless and it yanks your flashlight around the airport towards all of it. Towards everything except the book in your lap. Increasingly towards the Mountain Dew guy. You sit there ‘reading’ for 45 minutes without flipping a page. You start and stop the same sentences and paragraphs. You feel scattered. Eventually people around you stand up and form a line, and you join them. You board your flight.

• Good-ish: You’re wearing Bose 700’s and listening to brown noise on full volume and facing the tarmac and your book is really interesting and you’re fully absorbed by it. Your lighthouse is essentially shut out from environmental stimuli. Your prioritizer keeps your flashlight pointed at your book. After a long while, you feel a sudden inner prompting. Something is wrong. Your flashlight searches inwardly for more information and context. You remember you’re in an airport(!) and you look up and realize everyone has boarded your flight. You gather your things and race to the airbridge entrance and just barely make it onto the plane.

• Elite: Your lighthouse picks up and transmits all of the insane airport stimuli over to your prioritizer. Your prioritizer is super functional: it filters between noise and signal, and keeps your flashlight pointed at your book, until the PA announces a boarding call for your flight. You calmly put your book in your bag and board your flight.

The prioritizer is the entire ballgame when it comes to your attention. Your attentional strength and endurance depend on it. Whereas your alerting and orienting systems have their jobs—to absorb and be absorbed by stimuli—and they’re going to mechanistically go about their jobs whether you like it or not, your prioritizer can suck at its job. It can let you down. It can lose its grip. It can be confused by your inner turmoil and bamboozled by your environment. 

Your prioritizer can prioritize the wrong things, but it can also be trained, strengthened, protected, and supported—to the point where it can become the most valuable tool in your entire biological toolkit. Just imagine, for a second, having a super well-trained prioritizer which points your flashlight of attention on whatever you want, for as long as you want, while filtering out irrelevant background noise and alerting you when something genuinely important comes up. This is unheard of nowadays, but it is possible with enough training, support, and structure. When I say that I’ve gone from super distractible to a black belt in the art of attention, what has happened from a neurological standpoint is that my prioritizer has reached Herculean fitness levels. Everyday, before the day begins, my prioritizer knows the plan, and everyday it sticks to the plan. I will teach you how I did this. No Ksafe required. The roadmap is below.

The Triangle of Attention

On the path to restoring your prioritizer there are nine steps, and it’s best to ascend them in order. When all of the steps are complete and integrated, they come together to form a tripartite triangle. Failure at any level within the triangle will compromise and rapidly fatigue your attention, but they can be effortlessly managed and healthily maintained through habits, practices, and routines. The nine parts are grouped into three stages: environment, modes, and biology; which each break down into three separate steps. I will walk you through each stage and step. Here is how you can visualize them, as well as a preview of what each step entails.

Stage 1: Environment of Distraction

I’ll start off by sharing the software, systems, and tools that I’ve found most effective for managing phone, desktop, email, messengers, and more. And we’ll develop a plan for media consumption: news, social media, information, content, etc. 

1. Dimming the Lighthouse: managing unwanted stimuli, limiting unnecessary stress, and quieting rumination

2. Supporting the Prioritizer: preventing impulses and bucketing priorities

3. Intensifying the Flashlight: chemically enhancing wakefulness and readiness 

Stage 2: Modes of Focus

We’ll explore the three fundamental building blocks for improving your focus, and the progressive order in which you should understand and implement them.

1. Monofocus: unraveling the myth of multitasking, and exploring alternatives 

2. Unfocus: taking breaks to create a canvas for neural recovery and dot-connecting

3. Metafocus: reducing the latency of self-awareness through mindfulness meditation

Stage 3: Biology of Attention

Physiologically priming your body for focus. Science but hardly rocket science.

1. Fuel: the astonishing interplay between nutrition and concentration 

2. Sleep: the imperative battery charging process for neural restoration, focus capacity, and endurance

3. Flow: the importance of swimming downstream; and finding the intersection of challenge, skill, and purpose

Advanced Attention

Once you have a functioning prioritizer, you’ll be ready for Advanced Attention. These are the deep-cut, lesser known drills, practices, and behavioral changes that will allow you to improve your concentration beyond your wildest dreams.

1. Pre-Prioritizing: structuring the day to aid your prioritizer and protect your circle of attention

2. Resonance Frequency: using biofeedback to create a trigger for clarity, calm, and recovery

3. Pacts, Pledges, Accountability: leveraging the psychology of consistency and commitment

4. Believe It, Become It: reinforcing and living into a constructive self-image

5. Soft Zone Training: concentrating while the roof is falling in

Extras: Training, Practice, More

At the end (if there is interest), I’ll try to supplement the core lessons with short, actionable posts to support your progress in different ways: through challenges, drills, experiments, and by addressing specific situations.

• Attention @ Work - how to structure your time and manage interruptions when you’re not in complete control

• Training Plan: After I finish explaining everything above, I will share a prescriptive, structured 10-week program that integrates everything above so that you can see how it call comes together (drawing from the program I used to restore my attention)

• Practice Drills and Experiments: Like any other skill, concentration is something that can be practiced deliberately. Some drills will be in the 10-week training program, but there are plenty of additional supplementary exercises that you may want to try. 

• Mailbag: Along the way, if and when questions arise, I will round them up and answer them in FAQ posts

That’s the roadmap. Some of it is right out of the concentration textbook, and some of it is thirty hyperlinks removed from the mainstream world of attention. I’ll try to make everything more practical and accessible and easy to digest than I’ve seen elsewhere; and I’ll be specific about what you actually need to do. The order in which you progress is important. You must learn to walk before you try to run. So, start at the start. And as I’ve said before: this system is designed to work, which means that it will require hard work, (like everything that’s worth anything). I wrote it for people who are fed up with being scattered and who also believe that heightened powers of concentration will get them more of what they want out of life. If this sounds like you: I can’t wait to help you solve this problem.

When I’m locked onto the page I read 270 words in a minute. Usually I’m not locked onto anything. Usually when I sit down to read, or do anything for that matter, my mind wanders immediately off into the wilderness—chasing whims around the internet, scrolling downward into bottomless feeds, adding to phantom to-do lists, re-organizing those to-do lists. Like just about everyone I know, I have an attention span that can only be measured theoretically. This state-of-mind is a matter of grave concern when you have an imminent deadline, and it is enough to put you flat on your back when there are 600 pages of nineteenth-century Russian Literature between you and that deadline. In spring semester, 2010, I found myself in such a situation. I needed a workaround.

Fortunately, I found one. With my deadline rapidly approaching, I read Crime and Punishment in three hours. I didn’t just read it either. I highlighted, dogeared, Post-It flagged, and compulsively highlighted all but a few of its 211,591 words. That’s 1,175 words per minute. I then wrote a 10-page essay without ever rising from my seat and I submitted it that evening. I received an A. I’d quintupled my processing power. What was my workaround? Amphetamines. Specifically Adderall, from a contraband bottle in my roommate’s sock drawer. 

That happened on a Friday. Over the weekend I wasn’t thinking about Raskolnikov and I wasn’t playing beer pong in North Quad. Instead I hiked up into the San Gabriel Mountains to look over the Mojave; to sit alone on a granite outcrop and think. Upon that rock under the white fir, I may have appeared grounded, but inwardly I was wobbling. For many years I’d struggled profoundly to focus, and now I had finally taken the focus pill and it was breathtaking. I had a choice to make. On the one hand, I could continue to accumulate books faster than I could read them; on the other, I could forever read them faster than I could buy them. It was a Faustian Bargain, except, instead of trading my soul for the world of knowledge, I’d have to accept side effects like occasional nausea, increased anxiety, irregular heart rate, and an unnerving reflex to clench my jaw, which I seemed to do relentlessly as I plowed through Dostoevsky.

As a scattered student, the promise of attention on-demand was seductive, but the clear mountain air above Icehouse Canyon must have talked me out of it. I decided then and there that I would never take Adderall again. It wasn’t the heart flutters that worried me (worrisome as they were), it was the inevitability of dependence. I knew I was no match for it. I’d taken just one pill, and I was already starting to feel an onset of addiction to focus. Already, I could hardly imagine reading another book, not to mention living, without it. This spooked me to my self-sufficient core. I’ve been Adderall-sober for fourteen years, but all the while I’ve been searching for another on-switch.

For fourteen years I’ve tried and failed to increase my attention span the natural way. It became something of a Sisyphean obsession. I experimented with sleep phasing, eastern pharmacology, ketogenesis, time-blocking, mantras, and focus balms. I used and still use an app called “Self Control” to hide a quarter of the internet from myself. I took artichoke extract in a capsule on and off for a year. I canceled my AT&T contract, sold my phone, and disappeared from the cellular grid for four months. I survived a bootcamp in Onalaska, Washington, where I meditated steadfastly from 4:30 to 17:30, without saying a single word over ten days. I’ve tried virtually everything to increase my attention span, but my progress soon relapses with each new iOS update or news headline. There is an adaptive difficulty to concentration. The opponents improve at a rate that is impossible to keep up with.

Meanwhile, as I’ve tried to cling to my last atomic particles of focus, the attention-span of the world around me has been clinically dismantled by a booming attention economy. A lot can happen in fourteen years. The attention that I was struggling so hard to pay in 2010, is now a blue chip commodity. Attention, my attention and your attention, is bought and sold by you-know-who: Apple, Facebook, Google, TikTok, Elon, CNN, Fox, NYT, et. al. You know who, because by this point Big Tech’s onslaught on our attention is a tired storyline. The world has moved on to the existential implications of artificial general intelligence. Focus, concentration, and the entire enterprise of voluntarily directed attention, have come to represent quaint relics of a bygone era. The days of focus are over now. Abandoned and outsourced to a GPT.

As our ability to concentrate has collapsed, I’ve become more and more convinced that it is the superpower we should long for. Sustained focus is the engine that connects dots and builds things. To concentrate with the intensity of a chess grandmaster on the object of your choosing is to find out what you are capable of—what you are capable of knowing, understanding, creating, and becoming. "The concentration is like breathing—you never think of it,” says one grandmaster, reflecting on a game of tournament chess, “The roof could fall in and, if it missed you, you would be unaware of it.”¹ I hear this and wonder what my life might look like—what I might create and accomplish—if I could concentrate for just a few hours, let alone under a collapsing roof.

Besides the grandmasters, there are others who know the power of concentration. Concentration is how JavaScript was prototyped in 10 days. It’s what allowed Walt to develop Disneyland land in 366 days. It’s what powered Mary Shelley, when she wrote the first draft of Frankenstein in just a few summer afternoons. It’s what Edwin Land, the founder of Polaroid and inventor of consumer photography, credited for his legacy, when he said, “My whole life has been spent trying to teach people that intense concentration for hour after hour can bring out in people resources they didn't know they had.”

Above all else, blinders-on, self-directed focus is an essential ingredient on the path to personal fulfillment. Without it, you’re in the wilderness. It’s impossible to feel deeply fulfilled at work, in a relationship, in your one precious life, when your thumb twitches neverendingly towards red bubbles; when you have little control over what you spend your time thinking about. 

A few months ago, my fourteen year concentration crusade reached a boiling point. After wholeheartedly committing myself to sit down and make headway on my next business, my effort came immediately to a screeching halt to make way for an urgent incoming thought: How is Beyonce’s country album doing? Is there an accent over the e in Beyonce? I Google her name. There is an accent. And the album broke the single day streaming record. Wow, she has 320M Instagram followers? That seems like a lot. Like, a lot a lot. Is that actually the most? Isn’t Taylor Swift way bigger than Beyoncé? Huh, Taylor Swift only has 283M followers. Hmm, so no bad blood. Is Beyoncé actually bigger than Taylor Swift? This must be measurable somehow. How? Wait, who actually has the most IG followers? Wait what. Cristiano Ronaldo has 627M IG followers!? That’s like 1 in 15 humans. Isn’t it? What’s the global population now? 8.1B. Wow, so yeah closer to 1 in 14. That’s wild. Almost 8% of the world follows a football player. Also damn. Instagram must have so many users. Wow, 2 Billion MAUs. And more than a quarter of them follow Cristiano Ronaldo. That’s an underratedly crazy fact. Does he even post interesting stuff? Scroll, scroll, scroll, tap. Scroll. Yeah no, not even a little bit. Imagine if he did...

I came back into consciousness and found that I was looking at @cristiano’s Instagram page. My attention span had hit rock bottom. My self-confidence, receding unfathomably with it, was somewhere in the Mariana Trench. It wasn’t the first time I’d returned from a dizzying tangent that day and it wouldn’t be the last. In fact, it was the kind of tangential tangle that my days seemed to be made entirely out of. From the deep I wondered, How in God's name am I going to build my next business if I can’t hold and control a linear thought for more than a few minutes? I had no control of my mind, and I quite simply couldn’t take it any more. I decided right then that I would make concentration my total obsession. I would stop short of nothing in pursuit of focus. I would join the grandmaster at his table, and I would learn to stare at a problem unblinkingly until it began to smoke.

That journey started four months ago now. At that point I had something very much in the ballpark of ADHD2. Now I don’t. Now I sit down to do something and I don’t get up until it’s done, and I don’t think about anything else but the thing I’m doing. Over the past four months I’ve read 12 books about concentration and I’ve read even more studies. I’ve devoured everything that I could find on the topic, and I’ve made my life into an immersive experiment. I’ve figured a lot of things out. 

Most fundamentally, I’ve found that there are tactics for dealing with the external distractions, and there is applied theory for addressing the root causes of attentional failure. The root causes have to do with your brain, heart, and gut. Reconfiguring these things requires (very) hard work, but that’s how you fix your attention. Deleting Instagram is a tactic, (like so many of the things I tried over fourteen years). Delete it all you want, but the moment you re-download it (you will) you’ll find that your attention is as hopeless as ever. What you really want to do is fix the big problem at the bottom of the problems. You want to become totally undistractable, and to do that you need to address root causes. And unless you’re willing to make it your number one priority for several months, you will need help. I can help.

Having made astonishing progress myself, I’ve concluded that grandmaster-levels of concentration are attainable even for people with clinical levels of attention deficit. I don’t make that claim lightly, as someone who spent years trying and repeatedly failing to overcome chronic distractibility. I know that a leap like this is possible because I made the leap. At this very moment, I’m in the middle of doing something that I never would have dreamed possible a few months ago: I just wrote a draft of this essay in one sitting, over 3 hours, with no urgent deadline, while my wife moved ceaselessly around our old, rental mill house on creaky floors. This would have overwhelmed my old-self into an illiterate swivet. Now, I focus like this at will, everyday, whenever I want, for huge stretches at a time. Four months ago, a pin drop (real or imagined) was all it took to ruin a working session. Now it takes a SWAT team.

If I can do it, you can do it. It just takes a lot of well-designed effort.

It is a lot more difficult than popping amphetamines. It will take more than 10 minutes per day, and it will require more discipline than it takes to passively listen to Huberman Lab on your commute. The pursuit of ‘grandmaster-mode’ demands wholesale changes of diet, work habits, sleep schedule, fitness routines, communication style, and priorities. 

If you’re interested in legitimately transforming your ability to concentrate, I’ve designed a program that is instructive, progressive, and effective. I’m sharing it because I looked everywhere and couldn’t find it in one place—every book I read, while helpful in some way, was missing crucial components of the solution that worked for me. And when I was at my low point I would have done and given just about anything for a credible guide that treated me like an adult.

Through a series of essays and a structured system for ‘training’ focus, I plan to create a different kind of focus pill. Fewer things could be more important than reclaiming control of the thing that controls—your mind, your focus. Your life.

Thanks to for feedback on this essay

Eating Glass

After my second year at Claremont McKenna College, I took a leave of absence to hitchhike. I thumbed my way through Argentina, Bolivia, Uruguay, and Chile, where I dumpster-dived and slept in caves, in unlocked lifeguard towers, on sidewalks, and park benches. I’d become wary of comfort, and I contrived hardship. When I returned to school, I eschewed the dorms. Opting instead to sleep and study diagonally in my Honda Element, upon a low density foam folding mat which left me no more than eight inches of headroom. It was an oversized coffin with no lavatory. At night, I pissed into a Nalgene bottle.

Soon after graduating from college, I heard that the secret to success was doing the hardest thing you’ll do all day while everyone else was still sleeping—that made perfect sense to me, so for over a year I consistently woke up at 4:45AM to do 300 burpees on the sands of Venice Beach before sunrise. 

Something about pain always sat well with me.

I once ran a marathon on eight hours' notice without a single day of training, and believe me, that had some painful and lasting consequences. It seemed to me that pain was part of the reward. In this case, patellofemoral pain, a dull-aching daily reminder that I could do hard things. For the longest time, I wondered what my upper limit was. I searched steadily for it.

When I started my first serious company, Alltrue, pain wasn’t on my mind. Alltrue curated, produced, and sold socially- and environmentally-conscious products—an entirely wholesome and pain-free business premise. Pain was for feats of endurance and adventure. 

As it turns out, there would be pain. This time more psychic than physical. But when it arrived, I welcomed it as I always had. Pain threshold became a measuring stick for entrepreneurial aptitude. Like so many other experienced founders, I nodded enthusiastically as I watched Elon Musk give an interview, where he related the now famous mantra: “Starting a company is like eating glass and staring into the abyss.” And even more furiously as he continued: “You have to have a fairly high pain threshold. You’re constantly going to be facing the extermination of the company…[and] the most painful and pernicious problems... And that goes on for a long time.”

As that went on, I didn’t sleep much and I didn’t eat well, for many years. For many years, there were many days when I didn’t sleep or eat at all. And when the business really started growing, there were growing pains. 

At least once per quarter there were work-through-the-weekend, all-hands-on-deck affairs. Numerous all-nighters, when customer support tickets outnumbered customer support agents 100 to 1. There were times when litigation threats appeared in my inbox multiple times in a week. And when that same inbox was overwhelmed by boilerplate rejection emails from the investors we desperately needed. There were times (plural) when the monsoons of Rajasthan mold-rotted our products as they sailed in their shipping containers across the Indian Ocean, without much-needed desiccants. There was the time when thirty-thousand handbags were detained in customs-clearance-office-hell because of a byzantine country-of-origin labeling error. The time when we shipped ten-thousand room fragrances with defective nozzles, and the time when we had to recall seventy-thousand tea kettles at a cost of roughly eight hundred thousand dollars after CPSC attorneys fees, because the lids were missing a ⅛” steam vent.

Eventually it became clear that pain was part of the job. In fact, pain was the job. The job was: the constant dilemma of choosing which kind of glass to eat, while bearing the burden of responsibility for outcomes that affected hundreds of thousands of people: customers, employees, manufacturers, investors, et. al. Over time, the psychic pain compounded and morphed into a dread-y, low-grade perma-stress. It wasn’t all bad, of course. Oftentimes it was rewarding and hugely fulfilling. And in any case, I still courted discomfort in my free time, so a free dose of daily-work-pain was welcomed as a challenge.

Gnarly as it was, it was a good career fit: a game for people with great endurance in the face of repeated trials and constant pain. I could do pain. And as I continued to weather wildly painful periods as an entrepreneur, I kept coming back for more. It hadn’t killed me yet, and the company, ostensibly, grew stronger. I couldn’t find my threshold. So I kept knocking on the door. Finally, there was an answer.

Vomiting Glass

Imagine, you’ve been building a company for seven years—eating glass and staring into the abyss, for seven long years. 

And then finally and suddenly, way back in the furthest reaches of the blackness you see a light. You’ve sacrificed sleep and health and wealth and wellness and weekends and happy hours for seven years, all for the remote possibility of this: your company is going to be acquired. For nine figures. $100M, at least. The light. Freedom, financial and otherwise, forever, in the form of an inbound inquiry from an interested buyer. You hire an investment bank and drum up additional interest. The courtship continues. The buyer becomes more keen. You enter into exclusivity. 

Meanwhile, as you navigate the high stakes tango of M&A diligence, the perfect storm intensifies in the background. Then, all at once, it forms a tidal wave. A pandemic is at fever pitch. The global supply chain enters a crisis; the cost of freight shipping decuples.¹ Your marketing blueprint collapses, growth plateaus, then it declines.2 The capital markets freeze. Your lending partner pulls a vital line of credit. So does your shipping carrier. You’re running out of cash, quickly now. Now, your subscription rebilling date is out of reach. Your lifelines scuttle. Your situation is dire. Your lawyer tells you that you should talk to other lawyers who specialize in dire situations and those other lawyers tell you something very much to the effect of: “You are now in the ‘zone of insolvency’ and you have a fiduciary duty to put the business into bankruptcy. Immediately. M&A? Off the table. Prepare to lay off the entire team by the end of the week. Oh, they’re like family to you? Actually, you’ll need to let them go by day after tomorrow, over Zoom. One by one. And forget being set for life—this will bankrupt you. Yes, the business, but also you. Personally. Here’s the number of an attorney I recommend for that kind of thing, you’ll need it. Oh, and one last thing: don’t Google yourself for a while.”

That happened to me. I know what that’s like.

It’s like being swallowed by the abyss. Total blackness and morbidity. I contemplated suicide for the first and only time. It was the only way I could be sure to stop the despair. Creditor debt loomed large in my mind, but it paled in comparison to the feeling that slowly settled into my body and bones. Like a sponge soaking up cortisol. Every inbound message and official mail absorbed into the anguish: employees asking about severance, vendors asking about bills, state authorities asking about taxes, hundreds of thousands of customers asking about orders, credit card issuers pointing out personal guarantees, press outlets asking for comments. 

Investments in me, made by family and friends: worthless. 
Employee equity: zero. 
My net-worth: sub-zero.

Over the years we saved our company from the brink of death several times. But that was chewing glass compared to this. Every day of the tailspin made the day before it seem like a cake walk. Distress pulsed through my body mercilessly, while I buried my business in mirthless Zoom meetings with attorneys and liquidation trustees.

Bankrupting a company is like vomiting glass and being swallowed by the abyss.

So, what’s next? 

When the pain gets to be that bad, it etches itself into your psyche—a permanent reminder of where you’ve been, what you’ve done, who you are. It’s the psychic equivalent of the nagging knee pain that haunts an under-trained marathoner for years and years after the race. You don’t forget. You can’t.

Even still, I made a special effort to ensure redundancy. I wrote a 40-something page post-mortem which codified my experiences into principles. Things that were systematically wrong with the business, mistakes I made, things I did right. Mostly it was a remembrance, full of painful lessons that you couldn’t pay me to learn again.

But the world spins madly on, and before the dust had even settled people began to ask: So, what are you going to do next? In the world of business and small talk, you don’t win awards for licking your wounds.

It sure felt a lot better to say: I employ over a thousand people and run a business that grosses about a hundred million a year, than it did to say: I’m not working and I’m not sure when I will again or if I can again or what I’ll do. But that’s all I could muster. And as I mustered different variations of I don’t know, it became increasingly difficult to get the words out. I’d never considered the egoic impact of unemployment, of feeling low-status—of not working on something that impressed people, of not working at all. A deep inner urgency set in. 

And so, as people continued to ask about my next move I’d rattle off three or four ideas I was vaguely considering. Eventually, I homed in on the one that people nodded most agreeably to. I’d start the next great outdoor company, the next-generation-Patagonia. Publicly, it felt good to start solidifying something. Privately I had serious concerns about the viability and volatility of an apparel and gear business. It violated so many of the principles in the post-mortem I’d made for this very purpose.

To stop second guessing, I set up dozens of meetings with technical product designers, creative directors, and industry consultants. I deeply researched the outdoor space and most of its niches. I crafted a plan. I picked a brand name. I set a start date. And as the start date approached, I came across an illuminating study, which forced me to reflect on my neverending quest for pain.

The Pain Button

First, participants in the study were given a painful electric shock, then they were asked whether they’d pay to avoid being shocked again. Anyone who’d pay to avoid another shock was invited back. In the second stage of the study, participants were put in an empty room, alone, with no stimuli for fifteen minutes—no books, pens, paper, smartphones, nothing except a button that would administer the same painful electric shock as before. Before the fifteen minutes were up, 67% of the men pressed the pain button and shocked themselves.3 Astonishingly, they preferred pain to free-range thought, boredom, the unknown.

It was an all too obvious metaphor for my life. Here I was, palm hovering over the button. Ready for some pain. Vomiting glass? Better than nothing. I’d found the threshold, my upper limit. It turns out that it never had anything to do with pain at all. The threshold was and is the unknown. 

The masochism that prevailed in endless pursuit of activity, of feeling, of pain, was so much easier than the nebulous alternative: the unknown. Pain, it was so much easier to pursue pain, than to quietly peer into my own mind and ask the simplest questions: What is the feeling you’re really after? What do you really want? And then, to patiently wait for an answer.

The problem is, there is no answer. At least not right away. The world of the unknown is shapeless and unsettling. Questions like these create a vacuum, an invitation for our deepest insecurities and anxieties. A thousand unknowns rush in to fill the void.

It’s been two long years since April 12, 2022. Since I assigned my business to Armanino, LLP for the benefit of creditors. It’s been one year since I began asking myself, What do I really want? I’ve since been married, I’ve biked 3,500 miles across a continent, and I’ve moved to a new state, and still there are more questions than answers. My mind drifts to the unknown…

…I want to figure out what I really want before I run out of money. I want to figure out what happiness is. What enough feels like. Whether that’s a feeling I’m capable of feeling. I want to figure out whether I want kids, and why, and if so how many, and how I’ll afford to take care of them if I haven’t figured out what I want. I want to figure out why it bothers me when I imagine what other people will think about the fact that I’m writing essays instead of finding a job, or starting the-next-Patagonia. I want to figure out why I often find myself aspiring to make a dent in the universe. And why I so often find myself wishing I didn’t think about dents at all. I want to figure out why I want what I want, so that I can figure out if I really want it… 

Every question is Medusan: doubling, then redoubling again and again, into an ever-expanding chaos of unanswered and potentially unanswerable unknowns. 

The unknown is a struggle. Much more of a struggle than pain. Pain is easy. It’s something to do, it’s real, and maybe even knowable. Better the devil you know. Just press the button. It’s no wonder so many of us choose pain. And maybe we ought to sometimes—maybe we have to. Maybe some non-trivial amount of pain is requisite to a rich and meaningful life. But the deeper you explore the purgatory of existential personal inquiry—the unknown—the better your chances of discovering the things that are worth suffering for. A family, a relationship, a business idea. Not all pain is created equal. Some pain should be avoided. Sometimes it’s too much. And sometimes, unless you’ve done the work, you won’t know whether you’ve pressed the edifying pain button, or the traumatic, psyche-etching, with-you-forever pain button. Take it from me.

When it’s more comfortable to shock yourself than it is to simply stop and ask yourself why you’re about to shock yourself, that’s a clear sign that you don’t have the answers to some very important questions. When pain is easier than self-inquiry—when it looks like an easy, knowable, pressable button—before you press it, try asking: What is the feeling I’m really after? What do I really want?

Thanks to , , , and Antra Svarcs Richardson for feedback on this essay.