I had spent years learning math until that point, and I had never really bothered to ask: what even is a number? What even is the word “is”? This was the beginning of a rabbithole that spanned my first few years of college and involved encounters with real analysis, formal logic, Wittgenstein, and postmodernism. But it was a rabbithole that never ended in a satisfying way, and instead puttered out in a feeling of disillusionment. The entire journey centered around a question that has animated much of my life: how far can you get—or how powerful can you become—simply by sitting and thinking really hard about the most fundamental questions?

When I was starting out in college, I had this belief that on the other side of a deep engagement with the most fundamental philosophical questions is…something important. I wasn’t sure exactly what that something was. Enlightenment? A world-transforming insight? An end to all my suffering and even the suffering of everyone else in the world? A glitch in the very fabric of reality revealing itself and God bursting into the room and saying you found it, you found the secret to the puzzle!! ? I didn’t know what was on the other side of deep, intellectual engagement with the deepest questions, but what I knew was that every time I explored such questions (what am I? what is time? what is truth?), my sense of reality was expanded, and I somehow felt more powerful. A deep hunger was being quenched. A hunger to find the question at the root of all other questions, to find the answer that supersedes all other answers.

A decade later, I look at all of this differently. Today I’d say: if you spend long periods of time deep in thought about hard philosophical questions, what you get is…nothing worthwhile. It’s not a complete waste of time per se—you’ll certainly learn interesting things. But it’s not going to solve life in the way that you expect it to. It won’t be an end to your suffering. It won’t make you all-powerful. And you won’t come to some insight that will feel like a discrete “before” and “after” moment in your entire life story.

You might call the transition I’m describing the young philosopher’s disenchantment. The moment when you are no longer convinced that the most worthwhile thing you could do is go into deep thought about the most profound-looking questions. I have written elsewhere about why it is that philosophical inquiry can lead to this kind of disappointment, which essentially has to do with the limits of thought and language as a tool in solving problems (others have also expanded on this). But what I don’t see described as much is the first-person experience of undergoing this shift.

There are both benefits and drawbacks to a philosopher’s disenchantment. On the one hand, it entails coming into greater contact with reality.1 It is sort of like breaking out of a slumber you have been in your whole life, where you saw everything through the lens of abstraction, where you couldn’t appreciate things for what they were and instead always had to ask “but what does this imply about reality as a whole?” When I posted about “suddenly losing an interest in philosophical problems,” the comment from one of my best friends was “finally bro damn 💀”. It felt like finally seeing why everyone else kept rolling their eyes at my philosophical explorations, which always seemed to me to be the most pressing questions imaginable.

As much as it feels like a growth in maturity, though, the disenchantment has its drawbacks. It is, fundamentally, a loss of ambition. I am no longer working as hard to find The Ultimate Truth. When I read extremely abstract philosophy papers, my eyes gloss over, and any time I run into someone proclaiming their new fundamental ontology of reality, rather than getting excited, I get annoyed.

What’s strange about it, though, is that it actually feels exciting to contemplate that I could be wrong. It would somehow be satisfying to discover that some twenty-five year old philosopher actually did discover the real truth of the world just by sitting and thinking hard, and God actually did pop in out of nowhere and say, you did it, you won the prize!! (Or perhaps less supernaturally, we can imagine that said philosopher publishes their manuscript, and in short order science is solved, diseases are eradicated, and world peace is achieved.2) In such a situation I would be mildly upset that I wasn’t the one who saved the world by philosophizing, but I would also be happy that my childhood self was actually onto something, that philosophy really can change everything, and we actually did solve the riddle in the end.

I don’t expect I will ever fully let go of this philosophical compulsion – this desire to systematize every aspect of experience and try to extract fundamental truths from it.3 I still read various kinds of philosophy, or things that are close enough to it. But for the time being it feels like a relief to let go of that all-consuming search for a totalizing answer. My intellectual explorations now feel somehow more intimate and alive, even if I’m not pursuing them with as much urgency. I still study all these books and ask all these questions, but not because I think they will get me somewhere. I study them because they are beautiful.

I don’t just mean “peace” in the sense of “ah, feels nice to have a long weekend,” or “phew, they didn’t catch me in this round of layoffs.” I mean: everything is perfect and has always been perfect and there is nothing to worry about and I am one with God. I mean a peace that feels expansive, that makes you forgive everyone who’s ever wronged you and not identify with your mistakes or your accomplishments or your future plans. The kind of peace where you can sit and stare at unadorned drywall for twenty minutes and be gobsmacked by its beauty.

When you experience this kind of peace and notice that it is very strongly correlated with long periods of concentrated silence, you think, okay, I need to experience as much silence as possible. Can all you people texting me stfu please. Same with your coworkers, your email newsletters, social media, world events. You just want silence. You want there to not be things in life that you have to react to.

This is especially notable when you go on silent retreat, and you actually do shut out the entire world for ten days. You also don’t talk to anyone, read anything, or look at any screens. It’s just you and your own mind and the trees outside. And lo and behold, even more peace. Can we have this forever?

In theory you could. You could make your whole life a retreat, devote your existence to the practice of silent meditation. And maybe you’ll do that one day, but there are too many things you enjoy about life right now, like your friends, your parents, and good television. But you are stuck in a bind because the monastic life does seem more “pure,” it seems simpler. It’s frustrating to deal with all the disappointments of being a normal human with normal desires.

So you spend a long while being on the fence about this whole situation. You’re living your ordinary life but you somehow feel like you should be living differently. You shut your phone off for days at a time, but you find that turning it back on is always an anxiety-ridden ordeal. You say no to social plans so you can get your days of silence, but then you feel left out. You abstain from social media, which gives you a feeling of clarity, and then that clarity is quickly replaced with seething jealousy when you realize that your friends who didn’t abstain from social media became famous.

You are torn between two worlds and you keep searching for the epiphany that will get you out of this mess. But this time there is no singular epiphany that fixes the problem. It is instead a series of small and uncomfortable steps.

While your first retreat was amazing, the second one isn’t as good. It is somehow harder, and you’re not left with the months-long afterglow of the first one. You realize that the problems in your life continue to be problems, despite your many experiences of transcendence. You think to yourself, maybe those isolated moments of intense unequivocal peace aren’t what life is really all about?

By happenstance, you run into traditions which go about this entire project of human development differently, exemplified by the table below. The traditions you were more familiar with emphasize “saintliness, peace, renunciation”, where pleasure is bad and the ordinary world is corrupt. But there are also traditions that are about “nobility, heroism, mastery, play,” where the ordinary world is sacred and pleasure is good. You realize the space of spiritual paths is much wider than you thought.

You begin to wonder if you always need the ten days of silence or an entire hour of practice to get the presence that you want. You begin to think that the long periods of practice help, but you can also drop in instantly, because you are sort of already there. Omori Sogen: “It is said that if we sit for one minute we are Buddhas for one minute, and that even in one minute of zazen the whole truth in its completeness is embraced.”1

You begin to wonder if all the things you had shut away, that you believed were “distractions —work, interpersonal conflict, romance, cravings, social anxiety—aren’t themselves part of the practice. That the unpleasant emotions aren’t something to run away from. That there might even be something holy in the experience of being anxious before going to a party. Bruce Tift: “The sensations we flee from, that raw panic beneath our emotional strategies, might actually be the texture of openness itself, filtered through a nervous system that reads groundlessness as threat.”2

All of this feels like a new kind of adulthood. There isn’t one transcendental experience that marks it, of course, because the transcendental experiences are no longer the point. But you notice something has changed when you get home from travel and post online “back in town, hit me up if you wanna write together, meditate, go out dancing, etc”, and a friend you haven’t spoken to in a while responds: “I remember a time in your life when you said you couldn’t go out dancing because the music was too loud for your ears.” And you forgot you had said this. You’ve always been sensitive to the noise, of course, and you still are. But you no longer define yourself in opposition to it.

1. thesis: spaced repetition is an ick

(tweet from someone else)

Spaced repetition gives me the ick

It’s like the Soylent of learning. It’s a scientist’s idealized form of learning, stripped of all the natural messiness that makes learning rich and beautiful

Picture a mom using spaced repetition flashcards on her baby

Now picture that mom speaking lovingly to her baby about whatever’s on her mind as they go about their day

Which world do you want to live in? Where do you think the baby is better off?

The humane way to learn something is to be immersed in an environment where learning happens naturally, automatically, as a consequence of natural motivation and play

Think about all your most positive learning experiences. Learning your native language. Learning to move your body at playgrounds as a child. Learning to play video games. Learning how to use a computer by messing about. All natural, without instructions, or idealized, measured doses of learning

Natural learning is a beautiful human process. Spaced repetition loses all of that. We should flip our focus from learning random facts as fast as possible to crafting ENVIRONMENTS where skills and learning happen naturally

2. antithesis: repetition is glorious

(my response)

Ah, my sweet child. You think order and structure are tyranny. You think repetition is an ignoble thing, when in fact the vast majority of your life is repetition. Sleeping eating drinking shitting. Do you not get bored of having to do such things every day, like clockwork? Do you not find it “oppressive” and “inhumane”?

Take the dumbbell bicep curl. Up, down, up, down. How BORING, you say. So you put down the dumbbell and walk away, seeking something that feels more “natural”. And yet here is your friend, who stayed, continuing to lift the dumbbell, not shying away from “the ick.” Up, down, up, down. A few months later, he has done a thousand reps, and he is twice as strong as you.

You keep invoking what is “natural”. But there is nothing “natural” in sitting at a computer, playing video games, or artificially constructed playgrounds. All of it is made, not naturally, not automatically, but by people who were willing to do the same mundane task over and over again, people who submitted to a greater purpose than “whatever you feel like in the moment.”

No man steps in the same river twice, for he is not the same man and it is not the same river. No man looks at the same flashcard twice, for he is not the same man, and it is not the same flashcard. What you think of as “boring”, as “monotonous”, is indeed a sacred act for someone else. Each repetition, if you pay careful attention, is bursting with subtlety; each repetition is an opportunity to see it all again with fresh eyes.

You think repetition is dull, you think structure is tyranny. But in fact they are the opposite. Structure is freedom, and repetition is glorious.

3. synthesis: self-discipline without self-deception

What is interesting to me about this debate is not the effectiveness of different learning strategies, but the tension between “doing what is prescribed to you based on a plan/routine/social norm” versus “doing whatever you feel like in the moment.”

Over the years, I have oscillated wildly between the two. Growing up I viewed self-discipline as the highest virtue, and imposed a lot of control over myself. For example, after I did poorly in math in tenth grade, I spent the entire summer break waking up early every day to read a calculus textbook, so I could ace my eleventh grade class. Any time I had a goal, I would be extremely systematic about taking steps daily towards achieving it. This rigidity worked well for me for a while, but eventually it led to burnout and depression.

The story of the last several years has been: how can I follow my feelings and intuition more, rather than doing what some schedule/program/person says I “should” do? This approach has its virtues: I have moved much closer to a life I love, and I’ve become more creative. But I have come to realize that just doing what you feel like (some people call this “non-coercion”) also has its drawbacks. Ironically enough, it can also lead to burnout and depression, because the total absence of structure and higher-level goals can lead to taking the “path of least resistance” in many moments (lying down, doomscrolling, etc), which then reduces your energy and sense of self-efficacy, which then leads to even more bad habits in a downward spiral.

So in the past few months I have entered an arc of valuing self-discipline again. In practice this looks like: getting back into weightlifting, meditating for longer stretches, and being more restrictive about phone use, among other things. But underneath the surface-level behavior changes are some shifts in attitude that I think are just as important.

The first shift has been to view self-discipline more as devotion to something greater than yourself, rather than just as an instrument for self-advancement. I take a lot of inspiration from the Zen tradition here, which, despite being a spiritual tradition, places a rather extreme emphasis on austerity. (In the West, “spirituality” and “discipline” are often viewed as being in opposition to each other.) Take this anecdote of a Zen priest who was dying of cancer:

The next day, Priest Ryoen got up out of bed. He sat in Zen meditation on a folding straw mat slightly elevated above the ground. He said, “We are not expected to die in bed but in zazen.” Finally he fell into a critical condition. His nurse and disciples suggested many ways to make him feel comfortable, but he would not hear of it. When morning came, he went up to the Main Hall to recite the sutra.

He crawled from his room to the Main Hall, a distance of about 25 yards. Frequently lying on the floor to take a rest, he finally reached the Main Hall, where he chanted the names of the ancestral Zen masters to whom we owe the transmission of the Illuminated Mind. Chanting each of their names, he bowed in reverent worship of each master. He took a rest after every three or four names. In this way, he repeated his chanting day after day, until the dawn of the eleventh of September when he simply could not go to the Main Hall. When he passed away later that day, however, he was found seated in zazen.1

Imagine the kind of dedication it takes to be practicing until the literal moment you die.

The second shift that has made self-discipline more appealing to me recently is the attitude I tried to articulate in the essay above. There actually is a joy in doing the same thing over and over again. We live in a culture averse to repetition: we want to solve problems as quickly as possible by “one-shotting” them, and we are addicted to the endless novelty of social media feeds. We are impatient. But all of this is a kind of delusion because repetition is an inescapable fact of life. Or rather, what looks like repetition is inescapable – indeed, no two moments of experience are ever exactly the same, but they often appear to us as the same because we don’t care to really look at them. You become so much freer when you recognize that both novelty and sameness are essential to life, and “I’m back at the same place again” is neither fully true nor inherently bad.

We often resist discipline because we think of it as a kind of self-deception. We have an idea that there is a “true version” of ourself that we are shutting away, in order to do the “more disciplined” thing. Your inner child, say, or your soul. But the idea that there is one true being inside you, preformed and perfectly aware of exactly what it wants to do – that itself is a kind of delusion. You are and have always been an amalgamation of characters and tendencies inside you. And you have some conscious choice over which of those characters you feed, which of them you give more attention. Make that choice wisely.

In the weeks afterward I recounted this story to my friend Sid, and he said he was unsurprised that the conversation didn’t go well. When someone is tense, asking them “why are you tense right now?” will feel like an attack, and they are only going to get more tense as a result of that. Okay, I thought. Don’t tell someone that they’re being tense next time. But I was still left with the question: what should I do in that situation?

Until then, I’d operated on the principle that when interacting with a friend, it’s always a good idea to call out the uncomfortable, especially if you’re close friends. If I feel any inkling of unease in my interactions (or I infer that the other person is feeling uneasy), I need to say that out loud. Otherwise I’m not being an honest person. Real friends are supposed to be completely transparent with each other, and when there’s a problem, they talk about it until the problem is solved.

Now I recognize that talking about things often helps, but it can sometimes be a distraction. It all depends on what is motivating you to want to talk about the thing. Why do you want to call out the discomfort you’re feeling? Are you doing it out of genuine care for the other person or the friendship, or because you want to take control of the situation? The same words – “you seem uneasy right now” – can be said in very different ways, which will evoke very different responses. “You seem uneasy, is something up?” can mean I feel uncomfortable right now and I need you to fix that for me, or it can mean I care about you and want to see how you are feeling right now.

Nowadays I’m more aware of my own motivations in an interaction like that, and I can get closer to the heart of what I actually want to say. I no longer expect every interaction to be completely effortless, even with my best friends. So if I feel uneasy when hanging out with someone, the first thing I figure out is whether that is actually a problem that needs to be solved. Most of the time it is not: I can enjoy the interaction even if there are moments of discomfort. And sometimes the discomfort is a problem I want to solve, and in those cases I can bring it up, but without needing the other person to respond in any particular way.

My understanding of “authenticity” has begun to shift as a result. In any given moment, you have enormous latitude in what you talk about, what you direct your shared attention to. Being authentic does not mean vocalizing the most intrusive thought that pops into your head. It’s more like: confronting the situation in front of you with clarity. It’s less about disclosing everything, and more about seeing the other person exactly as they are, despite whatever gap in feeling or understanding might exist between you.

You’ll remember when you’re standing in the shower, feeling a sudden urge to pause the music and listen to all the sounds around you, locate yourself back inside your head and body, feel everything from your toes to your legs and arms and shoulders and back. You’ll remember again and you’ll feel yourself relax, you’ll feel the world collapse into an eternal present, but before eternity full takes hold of you, you’ll start forgetting again.

You’ll remember when you think to yourself: oh wait, it doesn’t matter that much whether I “finally” get in shape, whether I “finally” find community, finally settle down, finally get a clear career path. You’ll forget again when you’re meeting someone new at a party and have to explain yourself and your life path to their prying eyes in a split second.

You’ll remember when you take a few days off from work, you’ll remember when you see your parents for the first time in five months and say goodbye to them again. You’ll remember when you get one and a half day with your aunt for the first time in a decade before she too has to fly back home.

You’ll remember when you sit and meditate for long enough. But as soon as you remember you’ll forget. You have to make sure you sit for quite a while. The more you’re used to sitting, the longer you’ll have to sit in order to remember again. Unlike all your other memories this is not one you can willfully call to mind. Spaced repetition won’t do it either. It is a memory that comes to you on its own schedule. It is more like a spirit that chooses to possess you than a muscle you can voluntarily active. You simply set the conditions, silence the noise, light the candles, and wait to see if it appears. Oh wait—there it is right there. You just lost it.

You will remember on the worst day of your life, and also on the best day of your life. You’ll remember on your ordinary days. On a facetime call that feels like a timeless moment inside a spaceship, far away from earth and everything else in your life, disconnected, a home of its own. You’ll remember in some of your dreams, the ones that leave you waking up with a sense of peace.

The best teachers are the ones that help you remember. They will make you go: wait, really? Is it this again? I thought I covered this already. Look, here, I had a whole transformation about it years ago, I did this whole meditation retreat, I wrote blog posts about how important this was. People liked it! People liked the blog posts. My teacher told me it was very well-written. There’s no way I’ve forgotten. You’re telling me it happened again? And that this will keep happening?

And look, I hear you on the frustration. But aren’t you glad that you got to remember and forget at least a few times, rather than never having remembered in the first place? Hey dad, do you remember? How often do you forget? Do you think when we die, it feels more like remembering or like forgetting?

The meditators say that if you sit long and hard enough, one day you’ll remember and never forget again. But we’re not gonna hold out hope for that. We don’t have the time. What if forgetting isn’t actually a problem? At least, that’s how it feels when I truly remember. Every time I remember, without fail, it suddenly doesn’t matter that I forgot so many times. That is the joke that the universe plays on us. All of our supposed mistakes add up to perfection.

Thanks to Suzanne for feedback.

It takes two decades of storing everything in the cloud to realize that you don’t actually want infinite storage space. You accumulate hundreds of gigabytes of material – pictures, videos, journals, screenshots, downloads – little pieces of your life that you compiled and safeguarded as a way of remembering who you are. And you eventually realize that you compiled too much: it looks more like a garbage heap than a nicely curated gallery of memories. I have written millions of words in my journals in my past decade of journaling. If you look through my notes you’ll find a list of every task I completed for every single day since 2023. I’ve had stretches of months at a time where I journal thousands of words each day. And most of it means nothing to me.

There’s a trope in debates about life-extension: there are those who are obsessed with reversing aging and achieving immortality, and in opposition to them are those who say that the finiteness of life is what gives it meaning. I don’t think it’s finiteness that gives life meaning. I think it’s choices: the fact that you chose this path instead of that, the fact that you fell into this friend group instead of another, the fact that you chose to build a life with this person instead of someone else. What gives life meaning—to the extent that there is any one “source of meaning” in life—is its particularity: the fact that you have this particular history, this family, this collection of memories.

When you try to store everything, you reject the reality of choices. It’s easier to defer choices to some future version of yourself; take a picture of everything and you can filter through them later. Create a checklist for every task, document how you spend every hour of each day and save it in a spreadsheet in case it might be useful someday. It’s “optionality” taken to a psychotic extreme. Out of this compulsion is born products like Rewind, which promises to record everything you do on your computer and feed it all to an AI, so you can answer any question about what you’ve done, go back to any point in time. As they put it, it enables you to “remember everything.”

No one seems to question whether “remembering everything” is actually good for you. When you look at actual humans who could remember everything, you come to think of it more as a curse than a superpower. In his 1968 book The Mind of a Mnemonist, Alexander Luria documents one such case study. His patient, Solomon Shereshevski, or Patient S, could be read 70 words in a row and he’d immediately be able to recite them forward, backward, and in any other order. Luria struggled to come up with a single memory test that S would fail. And yet S’s superhuman ability to remember served as a major source of distress in his life. When recalling events, his mind would be overwhelmed with irrelevant details. His brain struggled with salience, to pick out the details of an event that actually mattered:

S was filled with highly detailed memories of his past experiences and was unable to generalize or to think at an abstract level. While the complex sensations evoked by stimuli helped him remember lists of numbers and words, they interfered with his ability to integrate and remember more complex things. He had trouble recognizing faces because each time a person’s expression changed, he would also “see” changing patterns of light and shade, which would confuse him. He also wasn’t very good at following a story read to him. Rather than ignoring the exact words and focusing on the important ideas, S was overwhelmed by an explosion of sensory experiences.

We all have a version of patient S inside of us. We can get overwhelmed with options, stuck in the details of a problem and unable to see the bigger picture. The tools we have – our cameras, our spreadsheets, our journals and databases – they can augment our minds, give us a degree of self-reflection and self-observation that would have been unthinkable in the past. But if we don’t use them carefully, they can distract us. They can hinder our judgement rather than augmenting it. I am a fan of all these tools; I like having more options, more memories stored, more information at my disposal. But I am not a fan of using technology to dissociate from the fact that nothing is truly permanent, that you can’t know everything. Forgetting is a crucial component of healthy memory; letting go, embracing not knowing, is a crucial component of being a healthy person.

A friend and I started a disappearing text chat the other day. This is something I’m generally opposed to because I like being able to read through old chats; I like being able to remember everything I’ve experienced. I once took my laptop in to the Apple store for a repair, and they unexpectedly had to wipe the entire device, and when I learned this I stormed out of the store because I had two folders in there that I never backed up. (Now I back up everything, on both iCloud and Dropbox.) And yet, I’ve found something oddly satisfying about the disappearing chat with my friend. We share a thought or a funny meme, maybe even something I’d enjoy looking back on, and a week later it’s gone. It feels like I’m carrying a little bit less, even though the whole promise of digital information storage was that it’s not supposed to weigh anything or take up any space.

None of this is to say that having more space is worse than having less. It’s good to have more space (and more options), but the more space you have, the more wisdom you need to make good use of that space. So by all means, take all the pictures you want, track your habits, journal every day, and document your to-do’s. But try to recognize sooner than later that you can’t actually hold onto everything. Even if we eventually reach the techno-optimist utopia of abundance, where we have effectively unbounded time, space, energy, and information, we will never have unbounded attention. We will always have to make choices about what to keep, and what to discard. Better to get comfortable with making that choice now, rather than having to let all of it go at once.

Special thanks to Aadil and Connie for workshopping this with me.

And underlying that is the following belief: the world is a dangerous place, and having good friends around makes it less dangerous. Notice two things: (1) on some literal level, this is of course true; (2) when this is your overriding view of what friendship is for (making life less dangerous), your friendships will tend to suffer for it. In my case it resulted in me always feeling like I need people around to make sure I’m doing okay and am free of danger. In particular there was (still often is) a lack of trust in my own judgement; I need other people around to double check my judgement for me. Specific ways this manifests:

• Whenever I made a big life decision I felt a need (notice – not a desire, but a sense of need) to sanity-check that decision with other people. Anytime I have an intense emotional experience (say, something makes me super anxious), I feel a need to discuss that experience with someone (a coach, therapist, mentor, friend), in order to make sure “things are okay and I’m not falling off the deep end.”

• Whenever I wanted to post something online I would feel a need to have someone else read it first, to make sure I’m not saying anything “too crazy” or something that I might plausibly regret in the future.

I thought of friendship (and more broadly, the people in my life) as a crutch to help me make sure I make the right decisions and avoided danger. (“Danger” here includes all kinds of things, from small things like social embarrassment to big things like injury and death.)

Now, for the past two months or so I’ve been working on addressing the underlying insecurity, lack of self-trust, and feeling of danger itself.1 Several interesting things have resulted:

• What I previously called “loneliness”, I now realize, was actually the insecurity. I felt like I could not trust myself to avoid danger, and so I always felt like I was deprived of something. Only if I felt like I was around someone deeply trustworthy (who also had, at this moment, the bandwidth to look out for me), did I feel like things were finally “okay.” Whereas now, I largely feel like things are fine regardless of who is around, and regardless of whether I am receiving affirmative feedback that I’m on the right track. When something bad or unexpected happens, I feel less of a need to immediately reach out and talk to someone about it to get reassurance.

• Connecting with people in general has become easier. Because my sense of self is not constantly under threat, I can be comfortable around a wider range of people. Do I need to know that someone is deeply trustworthy and will always be there no matter what in order to feel like I can relax around them? Clearly not.

• I feel less of a need to message friends with every little struggle. I feel less of a need to maintain connections with everyone to be sure that the friendship still exists.

The vision I’ve set out for myself is – can you trust yourself to take care of your problems as needed, and also to reach out for help to the extent that it’s needed too? I’ve found that by virtue of this increased security I also find it easier to reach out when I actually feel like I need help. In the past I would often just “struggle in silence” and secretly hope for my friends to check in on me, and then develop resentment when they didn’t. I was continually reinforcing this self-story of “I have so much difficulty with basic things and no one understands.” (If this seems like it applies to you, I strongly recommend reading about the Enneagram type 4 personality, specifically chapter 6 of this book.) Now that narrative is largely gone—life is a rollercoaster for everyone and you are perfectly capable of getting the help you need (and always have been).

Once this danger-oriented mindset around friendships is dissolved, you go back to viewing friendships in the frame of fun and enjoying the wild ride of life together. What was particularly striking about this process for me was recognizing that the thing I had originally pinned as the “core problem”—the lack of consistent yearslong close friendships—was not the most immediate cause of my unhappiness. I still think that long-term friendship and stable community are important, and I’m sure more of it would make me happier, but I no longer feel like something fundamental is missing from my life as it is. When you treat friendship—or anything else, really—as a crutch for an underlying insecurity you are doomed to be unsatisfied. No number of crutches will get you back to walking again.

(this is a casual follow-up to my previous post about moving.)

when people have been asking me the past few weeks how it’s been living in SF, I spare no hesitation to tell them I absolutely love it. indeed, this is one of the few “big decisions” I’ve made in my life where I haven’t looked back even once.

when I was graduating from college it seemed “cool” to shit on SF. it doesn’t feel that way anymore, at least not among the people I know. (I’m sure there are still some circles where it’s cool to shit on it.) SF is definitely an odd place, to be fair. all the billboards on the highways are about optimizing some aspect of your SaaS startup. it’s hard to get out of the “tech bubble” here, if you’re in tech or are adjacent to it. but I personally have stopped viewing this as a problem; at least, not enough of a problem to make me not want to live here.

it’s interesting to notice how much the fear of being a “tech bro” dominated my thinking and decisions a few years ago. I interned here one summer, and was inexplicably terrified of coming back. not because I had such a bad time per se…but because the idea of being here working as a full-time software engineer at some SaaS company and going climbing on the weekdays and going out on the weekends and occasionally playing board games with friends or whatever…something about that was eery. I think I was really afraid of a loss of a sense of identity. who am I? if I’m completely interchangeable with any other random software engineer in this city, that’s scary.

what I didn’t realize at the time is that your identity is never fully defined by the fact that you “live in X city and work at Y job.” your identity is defined by many more details than that: your friends, your passions, what you actually do at work day-to-day, your family, your pet peeves.

this “dread of being a nameless cog” was pretty overpowering – I would feel it even on brief trips to SF. but now I just don’t feel it at all, which would have shocked my past self. this dread almost never comes up these days because (1) I have a clearer sense of who I am now, and (2) more importantly, it’s clearer to me now that anytime I realize I’ve landed in a life or identity I don’t like, I have the power to change it. the dread is entirely based on a self-perception in which you won’t make the changes you need to make to be happy.

I like that people here are unusual. people have unusual interests and host unusual things. people here are intensely curious. I went to a birthday party where we spent the day reading the papers of a professor (along with a break to play frisbee and tag in the grass). that’s the kind of thing that I might have hosted myself in NYC, but it’s certainly not the kind of thing I was ever invited to in NYC. that same weekend I went to a “sunday night lecture” on fluorescent proteins hosted at a group house. these things exist in NYC but I personally was never that exposed to them.

people talk about “SF has nature” and I always thought they were talking about three-hour drives to Tahoe or whatever but actually there’s so much nature literally right here, here are some pictures I’ve taken on walks:

okay, there’s gotta be something that isn’t good about SF – what would that be? two things come to mind: (1) people like being flexible about plans, which I’m generally a fan of, but it occasionally gets annoying. it’s more normal here to just not commit to plans until literally an hour before the plan. (at the same time I have found that the non-flakey people show up more consistently.) (2) people try too hard here sometimes – as in, they try hard at everything. every aspect of your life is something to optimize/maximize. there is sometimes a sense of “if you’re not literally changing the world, wtf are you doing with your life?” one of the first things someone asked me upon meeting me is “what’s your theory of change,” i.e. what is the lever by which you are intending to have maximal impact on the world? I didn’t have an answer for her.

my favorite thing about SF is the same as my favorite thing about any other place: the people. really curious and thoughtful and also nice. I’m inordinately lucky that I get to live here with my brother and see close friends regularly. I see internet friends every wednesday and sunday at meditation night and coworking; I see my college best friends every weekend when we watch Severance. whenever I’d land back in NYC I’d feel a bit of dread, it’s just such an intense and overwhelming city. whenever I land in SF I feel…relaxed. like ah this place is nice and quiet and charming. it reminds me of Baz Luhrmann’s quote where he says, “Live in New York City once, but leave before it makes you hard; Live in Northern California once, but leave before it makes you soft.” we’ll have to wait to see when that happens.

something I’ve written about is a desire for long-term friendships and stability. the first two years I had in new york I craved that, and then for about a year and a half I finally had it and I wanted to keep it that way forever, and I was sure that me and my good friends were all gonna stay in the same place until we got old—except that another year or two later, I felt about as alone as I had felt when I first moved here.

to be clear, I had an amazing life in new york. I had hundreds friends and acquaintances, I was hosting regularly, I had a variety of different interesting communities I was a part of, and I loved my roommates. and yet somehow, four and a half years into my time there, I would often go to sleep thinking, “what kind of life have I setup for myself here, and why do I feel so alone?”

I think the version of me from a few years ago would have hoped that after five years in new york, I would be so settled, have such deep roots, that the prospect of moving wouldn’t even cross my mind. but instead, I somehow felt like all the work I had put in to building friendship and community just…didn’t amount to much. let me try to explain what I found unsatisfying about it, while also recognizing that despite all this I’m still one of the luckiest people in the world to have the amazing friends and communities I have—

in new york, everything felt transient. I constantly met new people, only to never see them again. everyone packs their social schedule, which makes it hard to make spontaneous plans, and some people pack their schedule with multiple social activities in a single night, which makes it hard to have the slow, several-hours-long hangouts I prefer. despite all the work I did to create social spaces that were not just about drinking in dark and loud spaces, it still felt like the “center of gravity” for social life was drinking in dark and loud spaces. I hosted tons of events, but the overlap between “my close friends” and “people who attend my events” was frustratingly small. I had friends in very different worlds, which is nice—but it felt like the worlds they were in were too different, and trying to host one big party where all my friends would be in one place seemed like a recipe for awkwardness, and people not really “getting” each other.

the transience was what got to me. I’ve always wanted something very simple: a small group of close friends that I see consistently, week after week. friends I feel comfortable just sitting with. friends I can make my stupid absurdist jokes with, friends who will prioritize me by setting aside an entire evening rather than just “let’s catch up between 7-8pm three tuesdays from now.” I had a semblance of that kind of community in new york for a while, but by the end of my time there it was nonexistent.

now the question is—what do you do about this? you’ve found yourself in a situation where you don’t have the consistency and depth of connection you want. there are two strategies: start where you are and make incremental improvements; or blow everything up and start from scratch.

for the longest time I was implicitly trying the “incremental improvement” strategy, and at some point I gave up. I still believe that at the end of the day, this problem is in my control, if I’m willing to put in the effort. there is a parallel universe where I actually did create exactly the kind of community I wanted in new york, and I’m still there. it’s just that building such a community takes effort. and between my work, my hobbies, and the various other preoccupations and interruptions in my life, I did not have much energy left for building and maintaining a close-knit community of best friends.1

and this is where san francisco came into the picture. I came here for a month this year to try it out, and I was surprised to find that I somehow felt more at home here than I did in new york. hosting and making plans felt less effortful than it does in new york because people were open to making plans last minute, and people were down for “slow, relaxed” hangouts that might take up an entire afternoon or evening. also, more of my friends here are into the exact same things I am (writing, meditation, obscure intellectual rabbitholes), and the circles feel small enough that even when I bring together friends from different worlds, there’s enough common ground to have interesting conversations. I was enjoying my visit so much that I even pushed back my flight to nyc to get an extra weekend here.

that month in SF showed me that maybe it’s time to try out the “blow it all up” strategy. that, as disappointing as it is to admit, I never ended up building the “deep roots” I wish I had in new york. the life I had built for myself was something I was willing to let go of.

so now I’m in SF, at least for the next few months. I handed off my new york lease and got rid of all my stuff, and found a sublet here. rather than insisting that any one place is the place I’m gonna be for the next decade, I’m leaning in to being a bit untethered for a while. the end goal is still to find a place and community for the long haul, but I’m no longer insisting that I have to know where that place is right now.

however long I stay here, I want to make the most of it. I want to make every place I go to feel like home, whether I’m there for a weekend or for a year. I want to be “that annoying guy who keeps inviting you to things / asking you to hang out,” at least until I feel like I’ve found some consistency in the people I see.2 I want to prioritize my closest friendships and not spend all my time doing “quick catchup over coffee” with people I only see once a quarter. I want to befriend people who are down to be silly and goofy. I want friends I can grow with, friends who are willing to be there for me, but who are also willing to challenge me.3

even with the frustrations about friend-making that I’ve written about, I can see just how incredible my life already is. there are a large number of amazing people in the world—some of whom I already know well and some of whom I haven’t met—and I have the chance of building lifelong friendships with a small number of these people. I work remotely and get to live where I want, I can use the internet to connect with people and share my thoughts, and some people are actually willing to listen to me and join the conversation. I am young, healthy, and free. and I know that with the passage of time I will find the community I’m looking for.

addendum / practical notes

a few other notes I couldn’t weave into this letter:

• if you’re considering a big move, consider one non-obvious benefit: shaking things up gives you better perspective on life, regardless of whether it ends up being the “right decision.” deciding to move helped me remember how temporary everything is. it forced me to have several cathartic “goodbye conversations” and get some things off my chest, and it also helped me realize that people appreciate me more than I had thought. in my last few weeks I saw more beauty in new york than I had in a while. I spent one of the nights of halloween weekend just sitting on the L train, riding it back and forth, getting off at random stops and walking around, appreciating how silly and joyful everyone looked.

• also, if you work remotely, moving is such an easily reversible decision! before I did it, it felt like such a huge deal conceptually to move across the country but like, literally it’s a matter of packing some bags and buying a flight and maybe buying/selling some furniture off facebook marketplace.

• it’s only been a week, but so far I’m loving SF. I’ve had lots of “cozy spontaneous hangouts,” like the other night when my brother invited me to a dinner with a few high school friends and we had dumplings and made vision boards. (also living with a sibling is so great, damn.) I organized a friendsgiving on very short notice and actually have a few friends coming that I’m very excited to see. I went to playspace (which was the original inspo for me to ping jaclyn and help her start cozy sundays). SF is also not perfect: some people are flaky and it obviously doesn’t have the energy of NYC, but it really has its own charm.

• the fact that apartments in SF are actually spacious and pleasant to spend time in is significant. across all the apartments I lived in in NYC I never had a proper, spacious living room. this makes it harder to have casual hangouts late at night—bars (or the rare community space like Verci) end up being your only option.

• if you’re in NYC and are looking for chill events to connect with others, check out midnight cafe! I helped start it and my cohost is continuing to run it. I also recommend fractal, verci, storytell, and telos haus.

• and if you’re in SF and interested in joining the events I’ll host here, fill in this form.

This is the question at the heart of much of our turmoil: am I making up rationalizations for why I should do this thing (e.g. move to a new city), or should I actually do it? Is my mind giving me excuses or is my mind giving me the truth?

The unfortunate reality of it is that there is no formula for figuring out the answer to this question in all cases. Our mind is a genius at making up excuses and rationalizing things when it wants us to believe something, so you generally can’t figure out the answer by thinking through the excuses themselves.

One of my main heuristics for this question is: Which way do you lean when you’re most happy and most confident in yourself? I recently made the decision to move to San Francisco myself, which has felt like a big and scary decision for a while, and some days I wonder if I’m just deceiving myself with the fantasy that life will be “better” in another city. But when I feel this doubt, I generally I go back to the moment where the decision felt clear: I was having an absolute blast there, and I thought to myself, yea, I actually really want to try this city, and anything else I say to myself is just cope for fear of making a life change.

Another thing I’ve realized is that you will never be totally sure. So it’s better to just give one path a try than to wait until you’re 100% confident in what the right decision is. It’s always tempting to wait so you can collect more information, but the more you wait, the more the situation in front of you continues to change (e.g. job prospects change, or some friends move from one place to another), and so you’re once again “behind” on having all the information you need. Also, there are some bits of information you only get once you actually choose one path or the other, and usually those are the most salient pieces of information (e.g. having a sense of what your actual social life would look in a city will only become apparent once you’re living there), so you will never have all the information you need.

Which way do you lean when you’re most confident? Or perhaps right after you’ve prayed, or had a really long, cathartic meditation? What do you feel when you’re most curious? Generally my motto is to follow curiosity and excitement, rather than fear. Of course, this motto is a corrective for what is, in my case, an underlying tendency to avoid risk. Maybe you’re the opposite and tend to lunge yourself into things fearlessly, causing needless strife for yourself—in which case, your motto should be “measure twice before cutting once.” In my experience, though, very few people are like this, and most people are too risk-averse, too averse to change, too constrained by their fears.

Generally, don’t spend too much time thinking about decisions. Now, this is hard to implement if you’re neurotic. One corrective for this is to lower the stakes of any decision, even a big one: you’re already doing fine, and you will not find heaven on the other side of your big decision. For the most part life looks the same, whether you take this job or that job, whether you live on this coast or that coast. No, I really mean that: it’s still you living that life, with all your neuroses and tendencies to doubt your decisions and your insistence on overweighing external factors on your quality of life. You’re the one that’s gonna be living in that other city or working that other career—you, the one who’s always wondering whether some other path would have been the right one—so you’ll still wonder now and then whether you’ve made the right decision. The life change is not gonna resolve all your insecurities.

There’s a deeper question here, which is: who are we, and how much of who we are is dictated by our environment? How much of our happiness is dictated by our circumstances? I don’t think there is a general answer to this question that will be useful for everyone. Of course, the happiest person on earth will probably be fairly miserable in a torture chamber, and the most neurotic person on earth will probably be pretty relaxed living in a luxurious communal home with loving friends and a bunch of cute dogs and cats. But my personal heuristic is to remember that I will overestimate how much my environment influences my happiness, and that wherever I go, I will carry the baggage of all my memories, personality traits and bad habits. And this is fine, because it also means that wherever I am, I am free to choose in any moment to let go of all my memories and personality traits and bad habits and instead respond to this moment with true presence, taking it in as the shining, novel, brilliant ray of experience that it is. I’ve found, for example, that sitting for eight hours a day quietly with my eyes closed and only eating two meals and not talking to anyone and having pretty much nothing else to do the entire day actually substantially increases my subjective quality of life (i.e., meditation retreats), and so I hesitate to hold any strong assumptions that I need some specific external factors to “truly be happy.” Remember how I said our brain is endlessly creative at coming up with excuses? It’s also endlessly creative at adapting to new environments.

Of course, your environment does have some influence on you. If you have nice art installed on your wall and a big window that lets in sunlight, you’ll have a slightly larger number of moments in the day where you go, “ah, beautiful.” If you live with good friends, you will feel substantially more relaxed when entering your home than if you live with strangers. If the weather is not too hot and not too cold outside, you’ll be more inclined to take long walks, which are likely to make you feel more energized and alive. But still, what I’ve found is that even with all these environmental supports, it’s possible to be utterly miserable, and it’s also possibly to be totally thrilled, and that’s just how this little brain of ours rolls. Your brain might operate differently—I know at least one person whose wellbeing is perfectly correlated with the amount of sunlight in his room, and I simply can’t relate to this, as someone who happily lived for two and a half years in rooms that never got direct sunlight.

The main thing I’ve learned about decisions is that you can never really know the right answer. We often ask ourselves whether we “should” be doing X or Y, and sometimes these should’s aren’t even about the specific decision itself (“should I live in New York or San Francisco”), but about the meta-factors relating to the decision, like “I want to go with the flow but I feel like I should have a longer-term plan.” Who said that you should have a longer-term plan? Who said that you should make decisions based on a spreadsheet versus a coin flip? The funny thing is that if you inspect a lot of your feelings that you “should” do this or that, you find that underneath them is fear and shame, not anything having to do with moral duty, which is ostensibly what the word “should” was originally about. Ultimately our tendency to ask what we “should” be doing stems from a desire to abdicate responsibility for our life and to have some external authority tell us what to do. And listen, I get it—for most of history we did have an authority tell us what to do (perhaps our parents, or our tribe, or our religious customs), and it just happens that today none of those influences have as much authority as they used to, and so we’re left with figuring out all the “shoulds” for ourselves, as individuals. My ask is that you face this reality head on, with poise, and recognize that at this particular time in your life and in history, you are responsible for deciding what matters. Sometimes a life decision is just a matter of taste, and other times the decision has actual moral import. Either way, embrace it and just choose.

Thanks to Susie for feedback on earlier drafts.

It’s a fairly simple strategy: whenever you notice yourself flinching away from this interpersonal friction, you can instead run towards it. Oh god, I said no to this person, what are they gonna think—oh wait, this is good, this is an opportunity to embrace conflict.

It helps to remember that ultimately you’re just afraid of a bunch of feelings. The other person doesn’t actually hate you; they’re not even thinking about you. You just have to get comfortable enduring that feeling of your stomach churning in on itself. And then you taste the liberation of not being bothered by someone disliking you, and it is genuinely euphoric.

It also helps to think through some of the edge cases, the catastrophes you’re actually afraid of, and to spell them out fully. Here’s one that often gets me: you’re afraid that if this person dislikes you, they’ll hold a grudge against you, and one day you might need something from them, and then this mistake you made years ago will come back and haunt you.

First just sit with this. Just recognize that this is one of your fears, this hypothetical future scenario in five years is dictating your actions in the present moment. You know that saying about how a butterfly flaps its wings and on the other side of the world a tornado starts? This is you: running around, frantically catching butterflies, with the hope that you’ll prevent a tornado. You’ve fallen prey to the illusion that you can setup a good life for yourself by attempting to control everyone’s perception of you.

The real remedy is to structure your life so that your fate doesn’t hinge on the whims of someone you ticked off five years ago. In fact, I’m sure this is already what your life looks like—for the most part, people you’ve barely interacted with don’t have any actual power over you. You can do more to serve your future self by positively creating a good life for yourself (which will often involve declining other people’s demands of you) than by minimizing the likelihood that anyone could possibly dislike you.

I have come to the conclusion lately that it is physically impossible to do anything important in the world and not have someone in the world upset at you. It’s impossible, but we try to convince ourselves otherwise. Even more broadly, it’s impossible to exist in the world without causing harm. Merely by breathing, eating, and walking around you are causing the death of countless little creatures. If you’ve spent extended time on the internet you’ll realize that it’s possible to say the most innocuous thing, and someone in the world will be inflamed by you, their experience will be made slightly worse by your words. And, well, neither of you are really to blame, it’s just that a particularly shaped match happened to come into contact with the correctly shaped tinder. Merely by existing you are constantly setting off little fires.

For some of us this becomes a source of guilt, and compels us to make ourselves as small as possible. Don’t state strong opinions, avoid conflict, don’t ever say no to someone directly, don’t criticize people. Minimizing harm becomes your primary mode of operation in the world. This is sad, because it makes us miserable and terrified of being ourselves.

Instead the question should be something else. The question should be: what’s the most good I can do, given the inevitable harm that will result from my actions?

When I look back on everything I’ve written in this blog, each post can be bucketed into one of two categories: nerdposting and feelingsposting. Nerdposting is when I write about something I’m interested in, primarily in the third person, with the goal of putting forward an argument or an explanation (examples: questions about the brain, revolutionary biology, or machine learning in science). Feelingsposting is when I share about my personal experiences and attempt to describe a distinct mood, with the goal of conveying some insight about emotions or life (examples: real life, give your friends a chance to abandon you). I’ve also occasionally tried blending the two, like in the problem of other minds or how to think well. But I’ve always felt there’s some incompatibility between them, and this post is my attempt at talking about my experience of writing each, and what I would like to focus on more.

Feelingsposting is a kind of public journalling. You use the written page to process and communicate lessons you’ve learned about how to live. I didn’t have an explicit intention to do this when I started this blog but that is how a lot of the essays have turned out. It’s easy for me to do this kind of writing because this is literally how I journal—many of the posts I’ve published were basically journal entries with a bit of editing. And I tend to get pretty vulnerable with these posts, like when I wrote about my relationship with my brother, or giving and receiving rejection. I sometimes look back at these pieces and think, damn, that was some pretty wise stuff. And clearly other people have found some value in them too: about 100k people have now visited this blog in aggregate.

And yet, these days I’m not quite as excited about public online vulnerability as I used to be. Writing about your emotions necessitates and encourages a tendency to ascribe a lot of significance to your emotions. Most of us already think about ourselves too much, and when you build a brand off writing about your emotions you turn this tendency into overdrive. If you’re not careful you start to develop some bad habits, like constantly mining your experiences for snappy insights to share in a self-help essay, or unconsciously believing that “if you don’t post about it, it didn’t happen.” In the extreme, it leads to a state of mind where anytime you have a remotely profound experience, you feel a craving to post about it on the internet as a way of validating that it was real. Writing just becomes a vessel for the ego to confirm that I Exist And My Experiences Are Important.

Contrast this with nerdposting. On one level, it’s harder than the personal writing because it requires actual research; and by virtue of the topic being less personal, it’s easier to be wrong. Anytime you want to make a claim about developmental biology or the philosophy of causation there’s a temptation to add five thousand footnotes to it, to read one more paper to make sure you’re not saying anything factually incorrect. But what I love about this kind of writing is that it forces me to spend more time thinking about the questions I’ve always been most fascinated by. In fact, in the past few months—in large part by virtue of deciding to focus more of my writing and tweets on explaining and synthesizing research in biology, AI, and other fields—I’ve felt a surge of curiosity and excitement about learning that is unparalleled even for me. I’ve never had so many rabbitholes that I’m eager to dive into, between the bioelectrical properties of cancer to the parallels between natural selection and learning in brains. The nice thing about this blog is that it adds more purpose to that quest: I’m reading not just to learn for myself but to find the most interesting bits and share them with you.

Despite all this excitement, I’ve hesitated to do more nerdposting here because I worry that “that’s not what people are here for,” that I will somehow overwhelm people with references to biology papers. Historically my more vulnerable writings have gotten more attention and new subscribers, and it’s very tempting to keep going down the path of maximal virality by doing more of that. This is often the suggested strategy for succeeding in online writing: once you find a “niche” that works, double down and keep exploiting it. I do want this blog to grow and I want to reach more people, but I want to do it in a way that feels true to my evolving interests and values. I actually can’t do it in a way that feels disingenuous.

All of that is not to say that I’m going to abandon feelingsposting altogether. It’s just that I don’t want to feel obligated to do that on a schedule: science essays can be put together weekly, but profound personal transformations can’t. I want to talk about my experience being a human, but only when I have something genuinely important to say on the matter; I’d like to spend the rest of the time engaging with intellectual questions. Questions like: How does biology construct itself from small parts? If scaling LLMs is not the path to AGI, what will be? How does the brain learn and create complex models of the world so efficiently? How did evolution stumble upon step-changes like multicellularity, cognition, self-awareness, and creativity? How do we create a more loving, wise, and less polarized society? These are questions that feel not just fascinating but urgent. I’ve tried to capture all of them in the new tagline for this blog: “deepdives into open questions in science, philosophy, and how to be a human.” It always comes back in one way or another to the fundamental questions about the universe and our place in it. Or as philosopher Gary Drescher eloquently put it: “WTF is going on and WTF are we doing here.”

The other night I was struck by a passage in Sean Carroll’s Endless Forms Most Beautiful, where he described the kinds of ideas I find most compelling, the eurekas that I’m most excited to read and write about:

The greatest “eurekas” in science combine both sensual aesthetics and conceptual insight. The physicist Victor Weisskopf (also a pianist) noted, “What is beautiful in science is the same thing that is beautiful in Beethoven. There’s a fog of events and suddenly you see a connection. It expresses a complex of human concerns that goes deeply to you, that connects things that were always in you that were never put together before.” In short, the best science offers the same kind of experience as the best books or films do.

That’s what comes to mind when I think about the phrase “bits of wonder” – little aspects of the world that, when you look at them more closely, open up into a giant window of mystery, and ultimately clarity and wisdom. Both the personal essays and the science essays have that same purpose: to help both me and you break through the fog of the world around us, and suddenly see the connection.

There are lots of things I don’t like about getting older. Your body wears down and your skin isn’t as vibrant and your knees and back start to hurt in strange ways. Each year you add more and more items to the list of “things to be careful about,” things you are no longer quite as capable of doing (all-nighters, intense bouts of concentration, several mile runs without any warmup). The possibilities start to narrow, you’re forced to make more and more hard decisions, and there are more and more attack surfaces for the feeling of regret.

But here’s a constant: each year you learn more about yourself. You see yourself in different environments, different styles of living, different communities and friend circles which reward slightly different things. You get to see yourself bend to the world around you as you evolve from one stage of life to another. When a caterpillar metamorphoses into a butterfly, every part of its body is destroyed and recreated—and yet it retains certain memories from its past life. As you get older you watch yourself change and you also get to see what remains the same.

I’m convinced each of us has certain fundamental dispositions, whether they’re contained in our genes or attachment styles or Enneagram types. But we’re also prone to making up stories about ourselves, stories that we wish were true. Time is the best antidote to all our attempts at self-deception: it’s easy to lie to yourself for a day, but a lot harder to lie to yourself for a decade.

I’ve always been fascinated by the idea of “the arrow of time”: the fact that the past leaves its traces in the future, but not vice versa. As you grow up you contain so many traces of past experiences, thoughts, and identities. The sheer number of traces is a source of strength: you have survived enough to know that all the challenges you fret about are never the end of the world. You’ve become wiser—you’ve spent enough time cycling through patterns of behavior (inner monologues, habits, principles) to know which ones are helpful to live by, and which aren’t. You’ve learned more about what kinds of experiences feel like a big deal in the moment but don’t actually mean that much to you in retrospect. You know better when an argument with a friend, or with yourself, is heading in a productive direction and when it isn’t.

As you get older you get bruises and burns, but your self-knowledge only increases. You make mistakes, you feel regret, but your self-knowledge increases. It’s hard for me to imagine what it’ll be like to have lived for twice as long as I’ve lived till now, to have read twice as many books and visited twice as many places and had twice as many arguments, breakups, weddings, funerals, career pivots, spiritual awakenings and late-night conversations. Much of it I am looking forward to and much of it I am dreading. But I know I’ll learn something from all of it. That each experience, good or bad, will play a crucial role in the person I am to become.

There is a gremlin inside my head. It’s grumpy and stingy and hard to please. It judges everything I do and everyone I come into contact with. Although I know better, I listen to the gremlin all the time.

The gremlin says things like, “the work you’re doing is not important enough.” It says “you’re not grateful enough, you’re not happy enough.” It’s quick to point out I should know by now how to work hard without burning out. It tells me to give up, it tells me that the people I admire don’t doubt themselves as much as I do. Silly gremlin.

The gremlin is not the same as me. It sits in the back of my head, its two hands clenched tightly to my eyes, tugging my attention from one place to another. The gremlin is the one that says, “Look, a threat! No, look here! No, over there!” The gremlin’s main mode of operation is to divert; it’s not very helpful for focus, or for kindness, or for rest. Its master skill is doubt: it knows how to question things, how to turn every sensation into an object of paranoia. (“That pain in your leg? It’s definitely cancer. Also M didn’t text you back because she hates you.”)

One day I looked the gremlin in the face. Unusual circumstances: I was up in the woods, hadn’t spoken to anyone for days. Time slowed down and I saw the gremlin for the first time, noticing that it has its own interests that are distinct from mine. I noticed the ways it was hurt. I noticed the gremlin is trying to help me but failing. I realized the doubt and paranoia do protect me sometimes, as much as they often hurt. I saw the way the gremlin channels all the maladies of our time—social media addiction, hyper-individualism, the commoditized market for attention and companionship. The gremlin is the twitter hivemind, the vengeful mob, the older sibling you could never please.

I suspect one day I’ll befriend the gremlin—not banish it entirely, but give it some room to assert itself, without letting it override all the other characters in my head. I haven’t gotten there yet, but I’m not in any rush. It’s easier, for now, to just look up at it every now and then, recognizing the distance between it and me, noticing the ways it’s trying to help. I don’t mind that the gremlin is there. I only take care to remember its existence, to acknowledge it whenever I’ve forgotten. There is a gremlin inside my head. And when the gremlin told me that this draft isn’t ready, I smiled and didn’t listen.

Thanks to Suzanne for feedback on earlier drafts.

Here’s the wrong answer: try to climb any kind of social ladder. I see people doing this often. They identify the people who others hold in high regard and try to associate with them. They position themselves in the center of these circles by establishing relationships with the right people and regularly advertising their position to others. All of us do this to some extent, but for some people it seems to be the overriding approach to human interaction. Their primary goal is to look impressive to impressive people.

All of that is the wrong way to go about things—even if the only thing you care about is status—because it is fundamentally limited to your existing social context. Popularity is, ultimately, a local phenomenon, and it takes effort to maintain, and without maintenance it withers into nothingness. It really doesn’t last: I’ve seen people succeed temporarily with this kind of social climbing—e.g. getting to the point of associating with literal billionaires—only to eventually be excluded from those groups because the relationships were devoid of substance.

If you want people’s respect, you have to have something real to offer them. Get really good at a specific skill. Be a genuinely kind person. Learn new things and become more interesting. Work on yourself rather than trying to navigate social ladders. Whatever you gain from that will last longer than having the coolest friends in high school. High school will end, and the social contexts in which you currently exist are bound to disband, while the skills you learn and the character you build will last you a lifetime.

Of course, the hope is that in the course of doing this, you will become a more mature person, you’ll begin to untie whatever knot you had that drove your obsession with status in the first place. Someone said recently that “most people are three secure friendships away from never thinking about status again.” While this is exaggerated, there is an important kernel of truth in it—your desire for status is inversely correlated with the degree of unconditional love you receive in your day-to-day real life. I’ve gone back and forth on the question of “how much to focus on status,” and I think it’s easy to swing between the extremes of “completely disregarding status/comparison and becoming a monk-like recluse” at one end, and at the other end “being totally and unrelentingly consumed by how you appear to others.” I think the right answer is somewhere in between, where you recognize that there are material benefits to impressing people, but you’re also wary of letting it be your overriding motivation for doing things. The real goal is to try to be a good person for its own sake, to pursue your curiosity for its own sake, at which point you’ll be both happy and respected, as you slowly find other people who appreciate you for your genuine personhood.

I made this meme recently about connection:

There seems to be a tendency among some circles, myself included, to think deeply about connection in order to find shortcuts to it. You have events popping up where people plunge immediately into deep personal stories, or do strange-looking meditative exercises like staring into each other’s eyes and narrating their inner monologue out loud. And to an extent it works: you suddenly feel closer to a group of strangers you just met than to most of the people you see every day. But it is somehow unsatisfying. You don’t just want more “connection highs”, you want kinship, you want a friendship that lasts. You want something that can’t be engineered over the course of one night.

I’ve known my friend for a decade. But it’s not only the passage of time that makes it special—it’s the ways we’ve shown up for each other, repeatedly, during that time. It’s the fact that he’s seen me at my worst—depressed, petty, impatient, self-absorbed—and for whatever reason, he chose to remain my friend. There was a night eight years ago, when I had been having a hard time and had been giving the people close to me a hard time, when I abruptly walked out of a group dinner because I was mad at everyone in the friend group, including him. Unlike everyone else in the group, he chased after me, and when he couldn’t find me, he sent this message:

Despite that fact that it’s been eight years I still remember that text exchange vividly, because I remember how shocked I was. Storming out of dinner is not something I usually do, and it’s the kind of action that I imagine would cause me to lose people’s good graces, that would make me seem like a petty child that no one wants to associate with. I was fully convinced that night, as I was wandering around feeling hopeless and angry, that those friendships were sealed, that the entire group was done with me. With just a few texts my friend showed me how wrong I was.

The fact that our friendship has survived moments like this is what gives me so much ease around him, it’s what assures me that I can be fully myself. A lot of people think of vulnerability as “sharing personal facts about yourself”, but this is the easiest kind of vulnerability. Serious vulnerability is not just talking about how you were struggling at some point, or that you were overwhelmed with emotion previously but are fine now—it’s sharing these things as they are happening, expressing your anger and anxiety and sadness while you still haven’t resolved them. There are very few people I can do this with, but it’s something I want to do with more of my friends.

If you’re like me, the thing you fear most is abandonment, and the thing you avoid most is putting yourself in a position where that might happen. And so you do everything you can to become self-reliant, you organize your life around independence, you develop an exhaustive list of practices to manage your own psychology. All of which are good things on their own. But I’m starting to wonder if, rather than avoiding helplessness at all costs, rather than fearing the day that I finally fall apart and truly need someone else, I can welcome such a day. I can think of it as “the beginning”, rather than thinking of it as “the end”. Because yes, sometimes friends witness you in such a moment and they walk away. But the right people will see you in your weakness and they’ll come and sit next to you. They will hold your hand and they’ll tell you, not with their words but with their actions: This is the moment at which I could abandon you. And I won’t.

Thanks to Suzanne and James for feedback on earlier drafts.

Real life is made of moments like this. It’s waking up with dread and clutching at your phone for relief. It’s being mildly frustrated at all your friends for the various ways in which they don’t understand you. Real life is wiping the lint from your dryer, it’s scrubbing the same pan clean for the hundredth time, it’s being surprised that even with all the fun of a friday night, you’re just as sad to say goodbye, just as sad as when you were a child.

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People will tell you to do different things. Some people will tell you to quit, to take the leap, because life is short. Other people will tell you to keep going, to stay committed, to play the long game. I’m not here to tell you either of these things. I’m asking you to stop imagining that either of these things is the answer, that either option is the thing standing between you and the perfect life you’re imagining for yourself.

We spend most of our time waiting, and very few precious moments feeling like we’ve finally arrived. We defer our willingness to bask in reality to tomorrow, and then the next day, and then the next, until we forget we ever deferred anything. You know that feeling you get when you hear the good news you’ve been waiting for, or when you’re so enthralled in conversation you forget that you haven’t checked your phone for hours, or when the rain has settled and you step into the forest and the freshness of the air wrests your lungs open and everything feels perfectly in place?

What if every experience could be like this? What if every moment could be “complete”? Meditation teacher Shinzen Young said he would rather have a single day of his life as a meditator, having attained what he’s attained, than forty years of ordinary human pleasures.

But what if you don’t need to wait until you’ve meditated for decades, what if you’re closer to that than you think? What if you were more often baffled by the fact that you’re still alive, if you began to ask of this moment, of every moment: what do you have to teach me?

You’re inflight, you’re falling through the sky, everything feels half-complete, there is so much more you meant to do, there are so many things you’re behind on, so many things you haven’t said. I’m right there with you. This is it, the madness we were born into and have no choice but to face. Real life is more and more of this and then it’s over.

Thanks to Trang and Abi for feedback on an earlier draft.

Okayness is when you feel fundamentally at ease with reality and with yourself. You feel like you are enough: there is nothing fundamentally deficient about you. You move through life with grace and fluidity. When bad things happen, negative emotions arise, and you just feel them, and then they pass, and none of that detracts from the fundamental beauty of your experience. Life feels inherently meaningful, you’re perfectly content with how things are, while also naturally gliding towards the things you want.

Non-okayness is the opposite. I’ve described it elsewhere as being “mildly disgruntled all the time.” You’re frustrated with life and with yourself. You feel like there is something wrong with you, although it’s a different problem in each moment: you’re too soft, you’re too rough, you’re too social, you’re too alone. You constantly feel like you’re in the wrong place and you “should have” done something else to avoid this situation. You’re often questioning what the point of all this is. You’ll still have moments of feeling excited and joyful, and you still have desires. You pursue those desires ardently in the hope that they’ll alleviate this emptiness inside you, and when they are satisfied, it definitely feels nice for a while, but soon you revert back to feeling frustrated and sad, and it’s almost as if you were never happy in the first place.

Here’s the thing I’ve had difficulty accepting: you can’t simply will yourself from the non-okayness state to the okayness state.

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The first meditation retreat I went to gave me a taste of what enduring okayness feels like. Up until that point, I had only ever experienced it in brief glimpses: perhaps a few days in a row at most. After my retreat, though, I felt like I was in that state for several months.

I distinctly remember one of my first days back in New York after my retreat. I was on PTO so I had the day to myself, and I didn’t have much of an agenda. Usually this is enough to put me on edge: I like maximizing productive use of my time, so I make detailed schedules and todo lists. If I spend an entire day off doing “nothing”, I’ll feel really bad and frustrated with myself at the end of it.

This day, post-retreat, was not like any day I had experienced before. It felt like literally anything could happen and things would be perfectly fine. I do some work? Great. I don’t do any work? Great. I felt like I could just sit there and stare at the brick walls of my apartment all day. I felt such unbridled affection for my roommates and friends. I started reading Stephen Batchelor’s Buddhism Without Beliefs, and felt moved by every paragraph. I could read for a whole hour without the slightest urge to use my phone. And even when bad things happened—one night I was hurt by something my friend did, another night someone at a bar yelled at me—I would feel upset, and then I’d move on, and it wouldn’t spiral into an endless internal echo of “I should’ve done this, I should be that, I should do that.”

This okayness lasted for a few months, but it slowly went away. One of the things about okayness is that it entails a lot of presence, and the more your sense of presence deteriorates, the less aware you are of the fact that it’s deteriorating. In other words, I don’t have much recollection of “losing it slowly” over time, I just remember feeling that way for a long time and then at some point not feeling that way at all. (Of course, memory is a finicky thing, so consider all this with a grain of salt.)

My point is: once I went back to my non-okay self, I wanted nothing more than to go back to the feeling of okayness. And I kept trying to figure out why that feeling went away, and how I could get it back. I blamed a bajillion different things. I thought it was my phone, so I’d spend extended periods of time on airplane mode. I thought it was because I wasn’t meditating enough, so I’d try to sit for 60-80 minutes per day. I thought it was New York, so I spent a few months in Toronto. I thought I just needed another retreat, so I went to another retreat. None of it worked: they would all give me some degree of okayness, but it never felt stable in the way that those months after my first retreat did.

I failed to recognize that entering stable okayness is a non-voluntary inner movement. There are many outer, voluntary moves you can do to make it more likely that the inner, non-voluntary move occurs, but none of them will reliably trigger the inner move. Being in a state of non-okayness is like having an internal knot in your mind, and the harder you try to untie the knot—the more you clench and tug on it—the tighter the knot becomes. Meditating for ten minutes might untie the knot, but you might also just meditate for ten minutes and still feel knotted. The longer you meditate, the more likely it is that the knot will untie, but again, you can’t untie the knot yourself, not directly. You could sit for an entire hour and still not get to where you’re trying to go.

Certain things nudge you towards okayness, while certain things nudge you away from it. The things that tend to nudge me towards okayness are: retreats, quiet time to myself, long walks, reading, and looking at beautiful things. The things that nudge me away from okayness are: consuming a lot of social media, socializing a ton, having a lot of deadlines. This doesn’t mean that those things are strictly bad and to be avoided at all costs. It’s just about working through your own relationship to these things — trying to figure out what it is about these things that uproots yourself sense of okayness, and address that.

One of the trickiest aspects of the inner knot is this: each time it gets tied again, it’s in an ever-so-slightly different shape, requiring a different move to untie it. You might have one meditation technique that reliably gets you there for a while, and then at some point it stops working, and now you need something else. You need a differently-shaped reminder, a differently-shaped piece of the truth, to get you back there each time. The shift that has been working for me most recently is to recognize that okayness just isn’t something I can reliably produce. And repeatedly asking myself, what is the truth of this moment, rather than trying to figure out how I can get to some other state, or some past memory or object of blame, that has nothing to do with what is going on right now.

All these things are little nudges to help make it more likely that you get to okayness. It’s anyone’s guess whether you’ll actually get there, and if you do, how long you’ll stay.