Substack tells me there are 7,000 people who have subscribed to this newsletter, of whom about 3,000 actually engage with it to some degree. Who are all you people?? I am so honored to be in your presence.

Here is my secret: writing this blog is one of the hardest things I’ve ever done. It feels strange to say that, because it’s such a silly little thing. But it makes complete sense. It is hard because I care. This blog is one of the things I have cared most about in my entire life.

If you’re not familiar with it, you can take a look through the post archive. I’ve written a lot of very vulnerable posts, and a lot of very effortful posts. I wrote ten thousand words trying to refute the philosophy of a famous physicist and writer. I wrote about my best friend moving away and how hard it was to say goodbye to him. I wrote thousands of words about all the things I have learned from meditation.

For today’s post I was originally going to write about “social media as a spiritual practice.” That is how I’ve been thinking about social media lately – engaging with it as another dimension of my spiritual and creative practices. Friends have been telling me that they’re enjoying my instagram stories a lot, so it seems that I’m doing something right. But before I hit publish on the draft, I saw a tweet about “let’s make a map of which spiritual teachers are to be trusted and which are fake.” And I remembered, I don’t like the way people talk about spirituality on the internet and I hate it when people present themselves as a spiritual authority. And even though I always try to preface my posts by clarifying that I’m figuring it all out myself, I still don’t feel good talking about spirituality. So I decided to defer the post to another day.

That is the kind of thing that makes writing a blog like this hard. There is so much you want to say, but there is so much that you are afraid of. I want to share about my life, and all the things I find beautiful, but I don’t trust the internet. The internet will take what you care about and rip it apart. I don’t want people’s stupid opinions to taint my own sense of what is beautiful.

I always have the backup option of posting stuff I don’t really care about. Sometimes I do that – I post something less personal, or something I wrote a while back and gave it time to gel. Something I got feedback on from multiple friends so they can confirm that I am not coming across as insane. But it is clear that there is something worthwhile in skipping all of that and coming into direct contact with this core fear of being seen and having no ability to control the other person’s perception of me.

There is so much I do want to say. Life has really been good in the past few months. Not “good” as in “I am feeling good all the time,” but “good” as in “I am falling in love with everything,” both the good parts and the bad parts. I want to tell you about that, but something about talking about it feels wrong. Like I still need to give it time to just be. I don’t like the way that the Algorithm distorts my own sense of what is important and what is worth speaking about.

I gave myself a challenge of publishing weekly for the past ten weeks, and this is counting as my tenth weekly post. This seems like a good spot to take a bit of a break. I have an intention of pausing for a few weeks and getting back to publishing in August. But something tells me that the form factor of this blog is just not quite right anymore. I started it 6 (!!!) years ago and I feel like a completely different person. I don’t like the title much anymore either. I don’t just want to give you little “bits” of wonder, little bite-sized doses, I want to blast your face with wonder, I want you to see the way that wonder already completely envelopes you. Blasts of Wonder. Lmao.

In the draft I had about “social media as a spiritual practice,” I was going to talk about how “posting on the internet is jumping off a cliff.” That is really the part that has made all of this hard. It is a direct exposure to the Blinding Light of the Unknown. You can publish a post and it can go number one on hacker news and random friends you hadn’t talked to in years are texting and emailing you about it. You can publish a vulnerable essay that you put a lot of effort into and no one responds, and your Saturday is ruined. There are ways to help cushion the fall, by being a bit more cautious, by turning off the notifications, not cross-posting on other social media platforms, distracting yourself with weekend plans. But you really can’t escape the fact that you’re falling.

I am so grateful to all of you for reading! I hope to be back soon. Also you can reply to these emails directly and I will respond, I would love to hear what these posts have done for you if anything.

I’ve noticed recently that there can be two different impulses underlying curiosity. The first one is “I want to understand this so I can control and optimize it,” and the second one is “I love this and I want to enjoy it.” I am calling the first motivation Conquest Impulse, and the second motivation Aesthetic Impulse. I believe these impulses often overlap but they fundamentally in opposition to each other: truly loving something means surrendering your desire to control it, and conversely, the need to fix/optimize/nail down something tends to get in the way of your ability to enjoy it. I believe these impulses apply to all domains of life, but for our present purposes, we can talk about the way they drive curiosity – the time you might spend reading, writing, consuming and producing ideas.

For me, Conquest Impulse was the dominant driver of my curiosity for a long time, and for years I was barely aware of it. I was seeking rational explanations for the things I was most curious about – I wanted a robust theory of knowledge, a robust theory of the mind, a robust theory of psychological healing, and a robust theory of reality itself. For example, when I wanted to study mechanisms of change in psychotherapy, I was really driven by this need to fix suffering once and for all; and in parallel I was driven by this desire to Make My Mark on the academic world. This same desire permeated my explorations in biology, meditation, and everything else I studied.

At the same time, the Aesthetic Impulse was also operating in these explorations. I recognized that one reason I enjoyed reading a neuroscience textbook how pretty the diagrams were. But the aesthetic impulse was always, in one way or another, subservient to the impulse toward conquest. There was a problem I was trying to solve, something I was trying to fix, something I was trying to prove to myself. This left little room for play and spontaneity, which eventually led to burnout.

In the past year, I have noticed the Aesthetic Impulse permeate deeper and deeper into the various things I do, slowly overtaking the impulse to conquest. So today, reading often feels like a sacred act. I am not trying to collect more information, and I’m not trying to Figure Out the Deepest Truths. I am merely reading, as wholeheartedly as I can. These days I am also spending more time appreciating art, and appreciating both the ugly and pretty things around me. My roommates and I have this giant pile of crap that we haven’t gotten rid of in our laundry closet, and looking at it has always brought me dread, and I have not done anything about it for over a year; but in the past week, I looked at the pile a few times and actually began to appreciate it, its three-dimensional shape, the texture of an old umbrella, the brightness and volume of the big plastic bag with junk inside it. I am enjoying books more, and I’m letting them change me, I am sitting with individual sentences I find dazzling.

Given all this, I feel distaste towards the way that Conquest Impulse dominated so much of my creative and intellectual endeavors over the years. So, when I see people working on an aesthetic theory of valence, I want to tell them to STOP. Part of me feels that they are missing the point about aesthetic experience; it is something to be enjoyed and befriended, rather than something to attempt to understand and theorize about from a distance (“seeing is forgetting the name of the thing one sees,” et cetera). At the same time, what I also feel is mere jealousy: that they are allowing themselves to attempt to conquer this subject, while I have, for the past while, been trying to disown that desire to conquer.

And that is what makes it clear to me that I am currently in an in-between state, where, having been subject to Conquest Impulse for so long, I am now disowning it and keeping it at arm’s length, to allow the Aesthetic Impulse to thrive. Years ago, I actually read an entire neuroscience textbook front to back, and these days it’s difficult to imagine myself doing that, and yet, I somehow feel that an uptick in that energy could be helpful for me.

So, I don’t think it’s simple as “conquest impulse Bad, aesthetic impulse Good.” The very framing of “Conquest Impulse” has a mildly negative connotation to it, but “conquering” or “mastering” can be good things too. We conquered electricity, and now we have beautiful desk lamps. We conquered construction, and now we can house large numbers of people in cities, in relative comfort. Spiritual practice is, in many ways, the cultivation of “self-mastery.” The attempt to understand and optimize and control things via systematic rational methods is useful: it is, as David Chapman puts it, what keeps airplanes in the air and the electric lights on.

But it seems important to not let Conquest Impulse completely dominate the Aesthetic Impulse, which really was the case for me for a long time. The Conquest Impulse is a lot more active and order-seeking, while the Aesthetic Impulse is more receptive, and requires surrender. And it makes studying things so much more joyful! It makes everything around you look more beautiful. It is, fundamentally, a more inspired state of being. I don’t know whether I’ve struck the right balance yet, but I’m enjoying making a little home in the Aesthetic Impulse for the time being.

Study hard what interests you the most in the most undisciplined, irreverent and original manner possible.

- Richard Feynman

Consider the most simple of words that we use countless times per day. The word “I”. I am happy, I am sad, I am here, I am on my way. What is “I”? What does it refer to? Therein lies a cosmic mystery that very smart people like Douglas Hofstadter have written 400-page long books about.

In the end, we are self-perceiving, self-inventing, locked-in mirages that are little miracles of self-reference.

- Douglas Hofstadter, I Am a Strange Loop, p. 363

It is not just the word “I” that is a mystery, but pretty much every single other word. When you say I am “happy”, what is “happy”? There’s another opportunity for a five-hundred page book, or a several thousand word wikipedia page. Every word you can utter can beget its own wikipedia page; hours and hours of analysis and citations and examples and references and etymological history, just for the word “happy” or for the notion of being.

It is mind-boggling that any of it is able to make even a shred of sense to us. Someone asked years ago on twitter, “is anyone else bothered by the fact that you can only define words with other words?” Yes, yes indeed, I am perplexed by this every day, the infinite web of concepts and associations that makes up ordinary human language.1

But here is the wonderful cheat-code about us humans: we can understand words, we can somehow take this infinitely recursive system of symbols and, over course of a childhood and life, make sense of it. A child begins by understanding the most “basic” words like “mom” and “dad”, their favorite foods, their favorite toys. Over time their vocabulary expands and they build a mastery of language. But the entire time—in my view at least—they never complete the mastery, because no human ever fully understands what words mean.

Here is the theory of “meaning” I subscribe to2: we build up our understanding of words over repeated life experience. The meanings of words take shape to us over time. When you are a child, “mama” means warmth, care, love, protection, food. “Mama”, to an infant, is the source of everything, the protector, mama is God itself. As the child develops they begin to recognize their mother as an individual human being, sort of like them. They register “mother” as a thing that exists in countless instantiations: everyone has their own mother. As they develop further they get to know their own mother as a person, her particular personality quirks and shortcomings and behaviors, what your mom approves of and disapproves of. What I am saying, basically, is that the word “mother” continues to take on more and more layers of meaning as you get older. As an adult, you read stories about motherhood, your read about histories of motherhood, your consume mythologies about motherhood, and your understand of “mother” gets deeper and deeper.

This seems to be the case for us for every word. You begin to understand “happiness” with more nuance, you understand the fine-grained texture of “I” better over time, the word “death” begins to mean more and more.

I am sometimes uneasy about how repetitive life is, how repetitive our utterances are. How are you, I am good, how are you, I’m pretty well, oh my God, I miss you, what is this, I love you, I want it, who am I. We say these things and we ask these questions over and over again. Is life just one big TikTok reel playing over and over again endlessly? Am I doomed to repeat myself over and over again? Of course not. You get a little bit closer to the heart of the matter each time you speak.

Do you think when a small child asks “daddy are you awake”, they know what the word “awake” means? When a first-grader says “I’m sad”, that they know the depth of what sadness is? When we speak of “the world” and “yesterday” and “tomorrow,” that we have any idea what we speak of? We don’t, yet we dare to speak nonetheless. We go all the way to the end of life with this rich and as-yet-incomplete picture of what this world is, what any of it really means, what the words really point to, we finish our life just barely understanding who we really are.

Thanks to Kenan for feedback on drafts. Cover photo is “Topological Zoo” by Anatoly Fomenko.

There are two questions one might contemplate when it comes to choosing a book to read:

1. Here are some books on my bookshelf. Which one do I feel like reading right now?

2. Out of all 150 million books in existence, which one is the best for me to read?

If you are susceptible to a certain kind of brainworm, you will tend to substitute the second question for the first. And you will take the same approach to life in general: out of all 150 million lives in existence, which one is best for me to lead? But for almost all the decisions one makes in life, this framing of the question is an objectively worse one to be contemplating.

But this framing is irresistible. The Optimizing Mind always asks: MORE! BETTER! BEST! How can I obtain the best? How can I extract the maximal amount of juice out of this life? Give me the OBJECTIVE answer!

This is greedy. We can think of this as the bad kind of greed, the Machiavellian greed for money and power. Or we can think of it as the greed of a child: the relentless, innocent desire for more experience. It is precious that children keep wanting to play, that they keep saying, “Do it again! Do it again!” As such, it is precious to be the kind of person who wants to read all the books, who wants to read the best books, who wants to learn as much as possible in life.

Back to the question: What book to read next? Which among the millions of hypothetical options to take? The problem with “oh my god there are 150 million books, what do I DO about this,” is that it channels a well-intentioned impulse (“I want to experience as much as there is to experience”) but applies the incorrect tool for it (Thinking and Optimizing, rather than Being and Doing).

I wrote earlier that I’ve been enjoying Ruth Ozeki’s The Book of Form and Emptiness. Another hundred pages since my last post (yes, I’m a slow reader), I continue to be mesmerized by it. In this book, the main character Benny hears voices in everything. To Benny, everything has a soul, everything is constantly speaking. As I have been reading it, I feel like I am listening more closely to the objects around me. One of the characters is obsessed with snow globes and now I keep thinking about snow globes.

There was no shortage of snow globes on eBay. They came in every color and theme and price range, and Annabelle was enchanted by the sheer variety. People were so creative to think of making snow globes in the first place, but then to make so many different kinds! She had her other collections, all her vintage toys, books, bottles, and postcards, each one with its own story. She hadn’t meant to start collecting snow globes, too, but the little turtle one she’d bought at the Thrift shop had cheered her so tremendously. It sat at the base of her main Mission Control monitor, and whenever she started feeling overwhelmed by the news, she would pick up the snow globe, turn it upside down, and watch the iridescent sparkles swirl and settle. There was no news inside the globe, and nothing ever changed. There, the world stayed exactly the way it was, and she found this reassuring.

Strange as it sounds, Ozeki’s book seems to be rehabilitating my relationship to Physical Objects in general. This relationship has always been strained: the physical objects around me either feel like a burden (too heavy, takes up space), or something I am overly attached to (and so I am terrified of losing or damaging it). For example, I get very attached to my physical copies of books, and I get bothered by the way their covers get frayed. It feels physically painful every time I look at it.

Over the years, this fussiness has toned down, and this seems to be accelerated by Ozeki’s book. She is making me appreciate the beauty of physical objects more while also not getting overly attached to them? I recently obtained a piece of bismuth at a store and I have been telling literally everyone about it. In a way, I treasure it as much as I treasure the book – I have been carrying it around with me most places I go and staring at it most nights. But, in an act of cosmic symbolism, little pieces of it has been chipping off over time, because bismuth is a relatively fragile mineral. When I first noticed this happening, I was devastated for a second, and then I threw the tiny little chips in the air on a hill as a sacrifice to the universe.

I feel a bit of grief saying all of this. Because as much as this is the exact kind of relationship I would like to have to the books I read (and to life in general), I can see the way that my Optimizing Mind begins to ask: OK, and how MORE? How BETTER? MORE transformative books, MORE books I really like, ALL the books, read ALL the books in case they affect you in the same way. Every time I have a sacred experience, my Optimizing Mind tries to figure out what it can do to capitalize on and appropriate that experience. Our culture owes us better than to have taught us this.

Back to the question, again: How to choose the next book? Well, how did I go about “choosing” Ozeki’s book? I didn’t really. I stumbled upon it at a bookstore. To be fair, I had been primed to buy it because I had previously read Ozeki’s other book, A Tale for the Time Being – but that also happened by accident. I got A Tale for the Time Being through one of those book exchanges where all the books are wrapped in paper and you pick one at random. So maybe it is more appropriate to say that Ozeki’s books chose me than I chose them.

I saw a video by Uncle Pappy the other day about the way we are always in a rush to finish things. He says: “You can try to complete a million checkboxes but you will forget all of them, or you can find a stream and spend the day sitting with it, and make a real memory.” I am perpetually burdened by all the books I haven’t read and the books I haven’t finished, but then I remember that this is the exact impulse that takes away from any one book truly moving me.

Thanks to Grant and James for feedback. Cover image by Jeroen Lam.

§ All creative practices involve inherently the same struggle

You might call it the struggle between “what you imagined you’d create” and “what you actually created.” When I first started drawing I wanted to get a break from writing because writing had become unpleasant in a way that was hard to describe.

At the very early stages the joy of drawing was very pure and refreshing. What I found over time though was that the same problems I had with writing would creep up in this new medium: perfectionism, frustration, impatience. It was a relief to experience this, because it helped me dispel the illusion that “I should stop writing” and instead recognize that “creative work in general is hard.”

There are also fundamental differences between drawing and writing that made drawing especially fun for me. It is a non-literal, non-analytical activity. It really grounds you in a way that writing doesn’t. It forces you to look more closely at the world around you. (FWIW: the best writing also does this, but it’s possible to do a lot of writing without getting this effect.)

§ There are no parallel lines in the world, and other illusions

There are a lot of little things you discover as you get into drawing about how your visual field actually works.

For example, a lot of lines that are parallel “in reality” are not actually parallel in your visual field. This is a very basic point about perspective that many people know, but it wasn’t until I started drawing a lot that I really began to see it everywhere. If you just look down a long hallway, it’s not immediately obvious that the far end of the hall is significantly smaller than the closer end. Your brain does a really good job of converting this “smallness” into a mental construct of “distance”, such that you no longer see its smallness at all, you just see it as “far away.”

There are so many other examples of this. A lot of “lines” that we see around us are actually just differently colored shadows falling on different sides of an object. There are far fewer actual lines in the world than it first appears. For example, in the pillars below, if you go right up to them you won’t actually see “lines” where the edges are; the appearance of all those vertical lines is just a byproduct of shadows. This is also very easy to see on window sills since they’re usually just one color but give you the impression of “sharp lines.”

§ We can see texture as much as we can feel it

As a novice you think drawing is fundamentally about geometry. And it sort of is, but texture is also a really big part. Texture is something that is essentially tactile but our eyes are really good at predicting what a texture will feel like just from the way it looks. And when you start looking closely at what different textures actually look like you get better at drawing them.

In the drawing lessons I’ve been doing, the instructor gives an example of how he used just a pen to evoke very different textures:

What I also found interesting is the instructor’s remark that all textures involve some mix of order and chaos. Just scribbling a bunch of random lines usually doesn’t give you the texture you’re trying to reproduce.

You may find a texture that feels like it’s just a bunch of nonsense, crazy chaotic marks. It’s not - it never is. There’s always some sort of rhythm to them, a flow that they follow because that’s how the physical world works.

Maybe what makes a drawing feel “real” is is that perfect interplay between chaos and order.

§ It feels so good to slowly get better at something

I often think about how Mark Zuckerberg learns a completely new hobby every year – jiu jitsu, learning Mandarin, et cetera. I can imagine this being really useful for cultivating a kind of youthful agility.

It is also hard to pick up new skills. But the great thing about all the online learning resources out there is that they give you the scaffolding such that it is always just hard enough that you’re learning something but still easy enough that it feels fun to do it. (Shoutout to Lev Vygotsky’s zone of proximal development).

§ Every field becomes more detailed and bigger upon closer inspection

There’s so many different kinds of drawing and disciplines in drawing, different tools, different schools of thought. Like, shading with a pencil is one kind of thing and shading with a pen is a whole different thing (it’s harder).

There are so many different kinds of drawing. There’s abstract drawing and more figurative work. You can take an entire course on inking or an entire course on observational drawing.

There is depth everywhere. A surprising amount of theory goes into simply drawing a box – you can draw it in one-point perspective, two-point perspective, or three-point perspective (or isometric if you don’t care about it looking realistic).

There is also subtlety to composition – the relative placement and size and occlusion of different objects in your scene is crucial for how realistic it looks. A good example is when drawing the legs of a dog – a beginner would draw both pairs of legs sort of flat, but with experience you realize you need the further legs to be partly occluded, partly higher up, and just a little bit smaller. Contrast the legs in the two drawings below:

§ How to start

I’ve mostly been following Drawabox which has a ton of free, very structured lessons and exercises (they’re almost too structured – don’t take the teacher’s prescriptions too seriously). Shoutout to my friends Song and Liam who have coached me a lot through this process.

I also like You Can Draw in 30 Days, although that one is in pencil (Drawabox teaches pen).

I’ve had Drawing on the Right Side of the Brain on my list for the longest time but haven’t read it yet; it seems to connect drawing to some of the Buddhist concepts I’m into: “the first thing you learn in painting class is emptiness…draw what you see, not what you know.”

You can learn a lot in just 15 minutes a day!

§ Proof of work

A sample from the first two months. Some box practice, some texture, some birds, some curvature, and some “form intersections” (modeling how shapes intersect with each other in 3d space). Also one Baymax.

I’ve probably drawn a hundred boxes by now…

I was getting dinner with a friend the other day who is entering a “transitionary period” in her career, and exploring a lot of existential questions about what to do next. Early in your career you have a lot of options in what to optimize your life around – money, career progress, settling down, exploring, enjoying your life. There’s a reason it’s called The Defining Decade – it really is the first decade (in our current social order) in which you have significant latitude to define what you want your life to be about.

A central theme of our conversation was regret. This friend of mine has an older friend, who is in his thirties, let’s call him Bob. Bob optimized for one kind of life – one that involves freedom and exploring his passions, at the cost of being less financially secure than his peers. Several of his friends own homes now, while he is still living with roommates. Bob wonders, when he visits the homes of his friends, and sees how Nice and Established their lives are, whether he’s made the Right Decisions.

In the past few months I’ve faced similar questions about what I want my life to look like long-term. I recently had a call with an old coworker who is in his late thirties to talk about this. What stood out to me about what he said is that “the 30s is the decade of regrets.” Pretty much everyone he knows regrets something about the life decisions they made. Some people regret working too hard and not enjoying life enough, other people regret neglecting their career and putting themselves in a precarious financial position. My mentor said he feels a little bit of both.

What I’ve begun to wonder over the course of having all of these conversations is whether regret might actually be fine. Not just inevitable but like, a good thing, actually. There are so many things that have to be true for you to feel regret about your life choices. You need to have lived for long enough to have made major decisions and observed their ramifications for your life. Not everyone actually gets to do that! Not only that, but if you are in a position where you feel regret, that actually means things are going well for you, for the most part. You have enough open time and space to reflect on decisions years in the past. When you are in the middle of an emergency—like war or illness or imminent death—regret about your career decisions in your twenties will be the last thing on your mind.

For some people, anticipated regret is a prison. And by some people, I mean me. I don’t know what it is exactly, but I’ve always had this tendency of taking responsibility for everything that happens in my life and believing that if I had planned things better, everything would be fine. In my first few years out of college, I was frustrated and lonely in New York, and I kept blaming myself for having chosen to move to New York where I had very few friends. (Incidentally, when I finally accepted where I was, I started making a lot more friends.)

I’ve had similar-shaped conundrums with relationships, friendships, career decisions, pretty much every decision you can imagine. I make a major decision, and then within a few months I blame myself (and the decision) for anything that hasn’t gone perfectly. There is a character in my head constantly waiting to say “oh my god you completely messed it up and if you had just done this one thing differently everything would be different and you should have known about this.”

This pattern has repeated enough times that now I am able to see it for what it is: a refusal to accept that I cannot control everything. A refusal to just accept things as they are. If I stop fixating on “this thing that happened in the past,” then I will have no choice to face The Unbearable Brightness of Right Now, which is way too bright most of the time. I have been breaking free of this pattern though. I don’t wallow in regret nearly as much as I did five years ago.

Feeling regret just means you’re conscientious and have enough open space to consider “what ifs.” I think of it as reflective of your personality more than the quality of your actual decisions. People often talk about it as, you regret certain things and not others, but I honestly don’t think I have ever made a big decision that I did not question at least once.

The only way out of the kind of regret I’m talking about is reduced self-absorption. There is a grief in all the things you didn’t do, and the mistakes you made, the times you didn’t say “I love you,” and so on. But that grief does not have to stick onto you and take over your life. That is a choice you are always free to make. To embrace the ways that things went wrong, and look beyond yourself.

Thanks James, Sam, and Grant for feedback on drafts.

Consider: I had a lot of social anxiety when I started tweeting six years ago. Early on, there was this person named Tom I had followed who was a great writer. Tom posted an interesting tweet, and I replied to it with a question. But Tom didn’t reply back for several hours, and I got so anxious about this that I deleted my comment.

A few hours later, to my surprise, Tom DMed me:

This was then followed by this exchange:

The “anxious King” comment really stuck with me. Tom provided the training wheels for my early exchanges on twitter, by letting me know that it’s normal to be this unsure of yourself when you’re just starting out. If he had never said this (or worse, if he had been actively mean), I might have gotten discouraged enough to give up on the whole tweeting thing altogether.

Five years and six thousand tweets later, I no longer need affirmation when posting a reply. I now reply to people’s tweets all the time and immediately forget that I did so. It shocks me, in fact, to think about how anxious I was in that chat with Tom. But it reminds me also to provide that same gentleness to other people who are just starting out. To supply the training wheels for people who are showing up with more hesitation and self-doubt than most.

Gentleness as virtue vs gentleness as weakness

It strikes me that there are two very different attitudes towards gentleness in our culture, both of which I resonate with.

View #1: Gentleness is a virtue. You have no idea what someone else is going through, and it can make someone’s day to be kind and supportive, to provide a blanket for their anxieties. We are all going through life for the first time. This view is captured nicely by one of my favorite internet memes:

View #2: People are too soft these days. Men used to go to war and you’re here deleting your tweets because no one responded. There is a social cost to all this emphasis on gentleness: everyone begins to feel responsible for taking care of everyone else and we stop respecting each other’s autonomy. The more gentle we are with each other, the more we reinforce this anxious, validation-seeking behavior. As some say, we should kill phrases like “no worries if not” because they make you sound weak.

The story of my life the past several years has been to shift from being firmly in the first camp (gentleness-maxxing) to slowly appreciating the benefits of both views. Thinking of gentleness as analogous to training wheels helps me synthesize the two perspectives. The truth is, different people need different levels of gentleness at different times. We are all working towards having the self-confidence and self-mastery to no longer need the training wheels, but depending on the specific domain and where you are in life, you may be closer or further from that point.

Bids for gentleness are a sign of competence, not weakness

Having spent many years as an anxious person who needed the kind of gentleness I’m talking about, there is something I have come to appreciate about people like me.

If you’re an anxious person, you tend to make “bids for gentleness,” usually unconsciously. Consider the socially anxious person who, when wanting to hang out with someone, says, “I would like to hang out with you but no worries if you’re not interested!!” Or even my own messages to Tom: “thanks for the message! yea I have a problem…I def need to work on it…thanks again.” To the receiver, messages like this may come across as insecure, and some people might even call it weak or annoying. But in my view there is an underappreciated form of competence taking place here.

What the sender of the message is doing here is, consciously or not, communicating their anxiety. They are in effect saying: “I don’t feel totally comfortable saying this but I am going to do it anyway—please be gentle if you have to let me down.” This is (1) courageous (they are doing it scared), and (2) a clear example of communicating your needs, even if it’s done somewhat implicitly.

In effect, the anxious person is sending out a signal that “I need training wheels for this particular kind of interaction.” In doing so, they will filter out people who lack the patience or interest in providing those training wheels, which allows them to find the right people who will meet the needs they have at this particular stage of life.

“Everyone is too nice” is a matter of feedback loops

I agree with the “people are too soft” camp in one sense: it’s possible to overdo the gentleness thing. But this usually has more to do with how people respond to the anxious person than with the anxious person himself.

There is a negative feedback loop that can happen which looks like this:

• You don’t feel sure of yourself, so you seek validation from other people;

• other people sense this, so they give you validation;

• but because everyone else views you this way, you keep thinking that you are someone who needs validation, so you keep seeking more of it;

• no one really tests the counterfactual of “what if we were more blunt with each other.”

We are very receptive to other people’s perceptions of us, so unless we are quite sure of our own needs, it’s easy for us to just go along with what other people think we need. If the subculture you are in has a norm like “humans are very fragile so we should all be super gentle with each other,” this feedback loop gets particularly strong. You might be more capable of taking punches than you (and other people) give you credit for.

The key is for everyone to develop the skill of being attuned enough to other people to have a better read on what they actually need. This is hard and takes a lot of time. Some people are naturally better at it than others, but I also think it’s something you get better at when you become more present.

In the right supportive context, gentleness is gradually not needed

When you get confident enough biking you can discard the training wheels. When you have enough reps of exchanging comments on twitter, you no longer need every comment to validate that it’s okay for you to be making comments.

It’s important to recognize, though, that there is no one pace everyone develops at. Our minds are complex and everyone has their own history. While I haven’t “solved” social anxiety, I do feel to be in a better place with it than five years ago – but also, five years is a long time to only get slightly better at social anxiety!

It’s hard to outgrow your anxieties if you’re constantly overwhelmed by them. You need to be “above water” in order to slowly get better, and that requires the right personal mindset and also the right external circumstances. Imagine you’re injured and need a crutch, and you also need to walk twelve miles a day. It’s going to be very hard to heal, although it may eventually happen, very slowly.

Conversely, if you are in a life situation where you can rest a lot, then you will heal much faster. You wouldn’t judge your broken bones for not fixing themselves quickly enough, you just give them the support they need. That is how I think about outgrowing our insecurities.

In the right place and right time, yelling can be supportive

I recently saw a viral video of a college basketball coach aggressively berating one of her players. It turned into an internet meme so you may have already seen it:

When I first watched it I had this familiar, triggered reaction: this is cruel, unjust, no one should be talked to like this. But there was a very illuminating New York Times article on the interaction which shifted my perspective. It turns out that there is a mutual agreement between the player and coach that this is what’s best for the player. From the player who received the yelling:

“Don’t tell me what I want to hear,” Okananwa, a junior, told Frese during one of their first conversations. “I want to be coached hard. I want to be elite.”

And the player and coach had this exchange after the yelling in the video:

It worked. After the game, Frese sent Okananwa a text: “Sorry for yelling so hard at you. However, I do love being able to coach you hard. I want it all for you.”

Okananwa replied: “Coach, you know I can take and always embrace your hard coaching for me. For the places I want to go, I need it. And thank you for holding me to such a high standard. It’s going to pay off for me in the future.”

To see two people reflecting on such a heated, aggressive exchange as a good thing was surprising to me. Of course, this can only happen after a requisite baseline of trust has already been established between the coach and player. And sometimes the coach can be miscalibrated! From the article:

To reach that point, Frese has tested players in practice to see how they handle yelling. She’s made mistakes and misinterpreted things in the past. If she yelled at a player during a practice but noticed it didn’t sit right with them, she would follow up to explain where she was coming from.

While I’m still not at the level where I can appreciate anyone yelling at me, I am starting to see what it looks like to be able to receive more frank (and even aggressive) support. I recently started working with a coach who, in the very first session we had, interrupted me and said “you’re monologuing with absolutely no affect, like you’re repeating a script. Start over and try again.” While in past years this would have felt hurtful, in the session it was extremely liberating, both because I was self-assured enough to not take it personally, and because I could tell it was coming from a place of authenticity and respect, rather than disdain.

Coda

This is what I think it all boils down to: approaching each person with respect for their autonomy. You can completely respect someone’s autonomy while being very frank with them. You can also completely respect someone’s autonomy while being gentle with them. To be attuned to other people is to be gentle when they need it, and blunt when they can handle it, while respecting and loving them throughout the process.

As much as I have been appreciating bluntness more over the years, I still have an affinity for gentleness because I understand what it’s like to need it, and to feel like the world is not able to offer it to you. As that famous song goes, “lean on me when you’re not strong; for it won’t be long till I need somebody to lean on.” Human existence has the tendency to be terrifying sometimes, whether that’s because you have a predisposition to anxiety or because you’re trying something new or because you are just going through a rough patch. Gentleness is just about holding each other’s hand for a little while as we endure that whole ordeal.

As you develop, you recognize the mind’s capacity to rationalize. To confabulate. There are annoying neuroscience studies about this but it is best appreciated as a personal experience. When you told a story about yourself that you later realized was a lie; you told yourself you cared about something or liked someone when you actually didn’t. You think, “oh wow, my stories about myself and what I say matters and what my principles are can be completely off base from the truth.”

Here something critical can happen: you can overreact. You start going, I don’t bother with stories at all. Who cares about life updates. In my own case it manifested particularly as an intense dislike of interviews. If someone asked, “why did you take this job?” what I wanted to say is How the fuck could I ever possibly know why I took this job, stop asking me that you underdeveloped imbecile.1

The way I actually think about it today is: yes, stories are not the full truth. Our own justifications for our lives are not at all a direct representation of what’s actually going on. (Be very mistrustful of all Substack writers.) But, they do shape our lives! The stories you tell do shape your life in some small way.

That’s why it is helpful to reflect now and then and say, “what is the coherent story I can tell about all of this?” What am I doing, what do I want, what do I care about? It is, of course, all a hypothesis! If you think you know yourself, you’re a fool. But if you think that your stories about yourself mean absolutely nothing, you’re only a slightly wiser fool.

Every time you try to tell a coherent story about your life, you shape your future actions in some small way. When I give my friends “here’s the update from the past month,” that is my ego trying to make sense of the vast ocean it is swimming in. Making sense of the ocean is futile, but useful. It makes you a little bit more reliable and definable as a person, which is helpful for functioning in society. It also helps you slowly orient towards greater alignment between the various parts of yourself (your ego, your body, your subconscious), which feels amazing. The ego is navigating the turbulent Ocean of Being in a boat, and when it tells stories it is simply…adjusting the sail to be more aligned with the winds. (Sorry I’ve never been sailing.)

Telling stories about yourself can also help you slowly get a deeper understanding of yourself. Just as we humans have a limited perspective on the world but we can try to augment and extend and deepen that perspective with science and philosophy and life experience, likewise our ego has a limited perspective on the Ocean of Our Being and it can try to augment and deepen that perspective by talking about itself and its experiences.

There is also just something precious about having wild things happen to you and being like “oh my God let me tell you about this story.” It sort of makes it more real you know. Let me tell you about The Final Time I Hung Out With Y because it is such a crazy and beautiful story to me. The more you let go of “life narratives as a false attempt at self-control”, the more you can lean into life narratives as an expression of beauty.

§§§

Smullyan is one of the most interesting figures I have ever come across. He was an accomplished mathematician and also a mystic; his wikipedia page describes him as a “mathematician, magician, concert pianist, logician, Taoist, and philosopher.” It’s quite rare to run into such a combination.

One of the things that Smullyan and I seem to share is that we have never liked being told what to do. In my own case, growing up with a successful and strong-willed older brother led to an intense desire to be my own person at all costs. To this day I am hypervigilant to other people’s attempts to control me, and have a complicated relationship to my own attempts to control myself.

This has naturally drawn both me and Smullyan towards Taoism, which is all about surrendering control.

Now, “surrendering control” is a big theme in self-help books in general, like the recently viral Let Them theory. But there is something else that drew me to Taoism and to Smullyan’s work in particular: there is a humor to his writing. The last thing he could ever do is take himself too seriously. And for someone who has approached their own personal development as One Serious Quest after another, that is a breath of fresh air.

Smullyan starts the book like this:

At all costs, the Christian must convince the heathen and the atheist that God exists, in order to save his soul. At all costs, the atheist must convince the Christian that the belief in God is but a childish and primitive superstition, doing enormous harm to the cause of true social progress. And so they battle and storm and bang away at each other. Meanwhile, the Taoist Sage sits quietly by the stream, perhaps with a book of poems, a cup of wine, and some painting materials, enjoying the Tao to his heart’s content, without ever worrying whether or not Tao exists. The Sage has no need to affirm the Tao; he is far too busy enjoying it!

Taoism, to me, is a philosophy of childlike joy. Unlike so many other philosophies, it does not shy away from paradox, absurdity, or ambiguity. In this way, it is a freer way of looking at the world than any other philosophy I’ve encountered. Let me share, for example, Smullyan’s passage on Crazy Philosophy and Sensible Philosophy:

I would roughly divide philosophies into two categories, “crazy” and “sensible”. Of the two, I definitely prefer the former. Sensible philosophies are noted for their sobriety, propriety, rationality, analytic skill, and other things. One definite advantage they have is that they are usually quite sensible. Crazy philosophies are characterized by their madness, spontaneity, sense of humor, total freedom from the most basic conventions of thought, amorality, beauty, divinity, naturalness, poesy, absolute honesty, freedom from inhibitions, contrariness, paradoxicalness, lack of discipline and general yum-yummy ness. Their most important advantage over the sensible philosophies is that they come far closer to the truth! Many philosophers of the “sensible” school will surely dispute this, and ask me whether I can “prove” this statement. My answer is, “Yes, quite easily, providing I am allowed to give a crazy proof rather than a sensible one.” But of course they will not allow this!

Crazy philosophies are known for their general yum-yummyness. If you had given me this passage four years ago, and I would have recoiled in disgust. What is this postmodern sarcastic pseudointellectual deepity nonsense. This exemplifies everything wrong with the irrational, unserious state of our civilization. It is the epitome of intellectual decay.

Today, I look at that passage, and I take delight in it. It makes me laugh. It want to print it out on a piece of paper and frame it on my wall.

Between the two reactions I can have to that passage, the latter is a lot more fun.

§§§

Naturally, any attempt to talk coherently about Taoism will come up short, because, you know, the Tao that can be named is not the true Tao. So rather than trying to put together a structured synthesis of what I learned from the book, or any “doctrine” that a true Taoist practitioner might advocate, allow me to share, via free-association, what Taoism means to me:

• It is impossible to ever get to the heart of what you want to say.

• The world was not “willed” into existence. It was not consciously and deliberately planned. Conscious and deliberate planning is what gives us skyscrapers, crosswalks, leather-bound notebooks, and a tedious tax code. The fundamental process of the world is a spontaneous one. Waterfalls, forests, nervous systems, and human conversations are examples of the fruits of spontaneity. The world, as a whole, is more like a forest than like a crosswalk.

  • The conscious planning is still part of the world, and it is the precondition to lots of amazing things in our world. But the precondition to the orderly planning is the chaotic spontaneity.2

  • (This is the part I imagine theists will most strongly disagree with, which is a conversation I’m very interested in.)

• Sometimes what you need is not more philosophy, but a slap in the face:

  A monk came to the Zen-master Ma-Tsu for enlightenment and asked: “What is the ultimate message of the Buddha?” The Master replied “I will show you. But when discussing such solemn matters, you should first make a bow to the Buddha”. The monk meekly complied, and whilst in the bowing position, the Master gave him a terrific kick in the pants. This unexpected kick sent him into a paroxysm of laughter and totally dissolved all his morbid irresolutions; at that moment he obtained “immediate enlightenment.” For years after he said to everyone he met, “Since I received that lack from Ma-Tsu, I haven’t been able to stop laughing.”

• Anyone who justifies their way of life with reasons and arguments is insecure. (It is natural to be insecure.)

• Foucault was right that many people’s claims to “objectivity” are indeed attempts at imposing their perspective on other people (but not always):

  I do not believe that you are consciously or deliberately hiding your subjectivity behind a mask of objectivity. You don’t know that you are doing this. And the only reason I am trying to convince you is my absolute faith that once you recognize what you are doing, you will no longer wish to continue doing it. You see, our main difference is that I have far more faith in the essential goodness of human wants than you do.

• When you believe in the fundamental goodness of human nature, it is no longer an urgent matter to control yourself or others.

• “Someone once compared freedom with Zen by saying that freedom is doing what one likes; Zen is liking what one does.”

• “In my simple opinion, those who are most intolerant of irrationality are not those who are most rational, but those who repress their irrationalities while at the same time “priding themselves” on being so rational.”

§§§

To see the point

Is to miss it completely

It was spring, and the rain had knocked the plum blossoms off the trees, and the pale pink petals lay plastered against the wet pavement. (13)

I loved this sentence. It made me feel something. But I was surprised at how much it made me feel, because I am usually irritated by sentences like this.

There is a wide genre of writing that is full of such sentences. Much fiction, much narrative nonfiction, and many artsy Substack posts. Sentences that set the scene, that go into painstaking detail about the surroundings of the story, but that don’t add to the story itself in any legible way. I have often struggled to see the “point” of such sentences. They have felt like the filler I have to wade through in order to get to the real “meat” of the book I’m reading – either the action (if I’m reading fiction), or the insights (if I’m reading nonfiction). Those are the things I am really reading for.

Over the years, I have come to appreciate such sentences more. They’ve begun to glow. The core shift has been from what Tyler Alterman calls “instrumentality” towards “autotelicity” (or: The Church vs Mystics; The Enlightenment vs Romanticism). “Instrumentality/autotelicity” are two big words which capture something simple: whether you are doing a thing for some purpose beyond itself (it is instrumental towards something else), or whether you are doing its own sake (autotelic - from the greek auto meaning self, and telos meaning purpose).

My arc as a reader has been to embrace autotelicity more over time. There is something beautiful in the mere description of “pink petals plastered against the wet pavement.” Sure, it serves some purpose beyond itself – in this case, depicting the gloomy mood of a rainy day, right after a mother and her child attend the funeral of the boy’s dad. But really, the value of the sentence is inherent to the sentence itself. There is a beautiful metaphor in it (the petals being plastered in the same way that a wallpaper can be plastered onto a wall). There is also a satisfying alliteration – pale pink petals plastered pavement. There is even a rhythm to it, with each clause in the sentence getting progressively longer and more detailed.

One way to appreciate beautiful sentences for the sake of themselves is simply to get older. The older you get, the more experiences you have, and the more experiences you have, the more you can draw on when absorbing other people’s descriptions of their experiences. If you’ve never seen paper plastered onto a wall nor seen petals on the pavement after a rainy day, the connection between the two wouldn’t be striking to you. If you’ve never had the experience of grief and the juxtapositions involved in it—the sense of both gratitude for what was and sadness for what’s been lost—the contrast of grey skies and colorful blossoms wouldn’t mean as much to you.

But the bigger impediment to enjoying these sentences is the belief that your reading has to be constantly getting you somewhere. It takes presence and gratitude to appreciate the act of such an aimless activity as reading a book – and not just any book, but a novel in particular. And not just a novel that is packed with drama, but the kind that meanders, the kind that takes its time. It is a kind of rebellion in our world to appreciate such works; our world where every action is framed in the service of a greater cause, in the service of some instrumental benefit like more power or prosperity. It is rebellious to let the sentence stand on its own, to read the sentence, to look at the petals plastered on the pavement, to look without any further agenda than looking itself.

my spiritual friends are finicky. they are very sensitive to sounds and smells. they are bothered by loud parties just like I am, aware of the way the loudspeakers’ vibrations burn into their inner ear. they are not into alcohol as much, and they don’t do drugs casually, only with a proper air of respect and sacredness.

my spiritual friends are weak. they don’t “toughen up” like my other friends do. they don’t just push through the unpleasant. they are more willing to walk away. my spiritual friends make a habit of escaping.

my spiritual friends are geniuses. they are the most ambitious people I know. they don’t settle for the status quo. why the hell should we settle for ordinary material pleasures, socially sanctioned successes? they are willing to let go of everything.

my spiritual friends are unlike my ordinary friends, the ones who compartmentalize, who put the unacknowledged pieces of their psyche in a drawer behind a closed door, not to be touched until decades later. not to be touched until a midlife crisis or psychosis in their sixties. my spiritual friends open the pandora’s box today and let it all spill out in the open, orderliness be damned.

my spiritual friends are fuckups. how could you not be? they have either fucked up life or life has fucked them up. ordinary people just go on vacations; me and my spiritual friends go on retreats. my spiritual friends and I all had the moment when the veneer of our personality began to show cracks, and we realized that it would not work to try to tape it back together again. so we let it all fall to the floor and shatter, and then we began the painstaking process of rebuilding the house of self, step by step, this time with a more rooted foundation.

I look at my spiritual friends and I see my own shadow. all the ways I’ve slowed down and fallen behind and not been as functional as I should be, as functional as my ordinary friends.

I look at my spiritual friends and I see my own brilliance. I see people who care so much that it hurts. I see people who opened their heart and let the world burn them, and dared to open their heart further after that. people who answered the call to something greater, who looked past the drama of winning and losing and asked what more there might be.

sometimes I look at my ordinary friends and I feel jealous, of how simple their life seems to be, how their day-to-day is not so heavy and disorienting as it is to me. other times, I look at them and think, man they are missing out on the greatest show of all time.

when I look at my ordinary friends I try to think of them as not so different from me. maybe they are further ahead than me or maybe they are very far behind. sometimes I look at my spiritual friends and think we are all confused, and other times I think we have figured it out better than anyone else on earth.

I look at my spiritual friends and I thank them for keeping me company.

thanks to grant for feedback on drafts.

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.

What picture of the world do Newton’s laws evoke? Here I’m not interested in the specific equations of motion he wrote down, or his technical definitions of force, acceleration, and inertia. I am interested in the intuitions and metaphors underlying his theories. As humans, we understand everything by metaphor1 to our basic, everyday experiences, and for most people, Newton’s laws draw on very particular metaphors:

The world is like a bunch of billiard balls. What are the salient properties of billiard balls from our perspective as humans? First, the balls are atomic: they are indivisible and featureless units. There is nothing too interesting about them beyond their interactions with other balls. Also, they are inert and unalive. They don’t feel anything of course, they’re just rocks.

And what about their movements and interactions? Their movements and interactions are all predetermined. Strike the balls in the same way, and they will follow the exact same paths. Also, their interactions are all local: the only thing influencing the movement of one ball is the direct contact it has with other balls (or with the edges of the table). Everything that happens on a billiard table is just a bunch of bumping and shoving. Out of that bumping and shoving comes everything we care about in a game of billiards, all the patterns and strategies and gameplay narratives. It’s a bunch of inert, uninteresting, featureless rocks bumping and shoving against each other.

The “scientifically minded” person who has not spent much time thinking through their metaphorical handles on reality sees all of these things as properties of the world in general. The world is a bunch of billiard balls that move. The world is a bunch of puzzle pieces or lego blocks. The world is fundamentally dead, predetermined, and unwittingly, imperturbably subject to the progression of math equations. What’s interesting is that even after realizing that the theory itself is technically untrue (quantum mechanics has superseded Newton’s laws), the metaphors underlying the theory stay with us.

There is a philosophical name for the worldview that results from this picture: mechanism. And mechanism, as a way of looking at the world, is one of the most powerful things we have ever come up with. Thinking of the world in terms of local bumping and shoving, featureless subunits that grind against each other like gears and pulleys, has given us, well, incredibly useful inventions. And it continues to be a useful orientation for science today: we seek a mechanistic understanding of black box AI systems, and we try to decode the marvels of life through mapping out its biomechanical foundations – the shapes of proteins, the graph of neurons in your head.

Of course, we also know today that mechanism is not the full picture of reality. The elementary particles of reality are not actually featureless (and they might not be unfeeling), local “bumping and shoving” is not the only legitimate form of interaction, and the universe might not actually be fully determined by its initial conditions. Research programs that operate exclusively in terms of mechanism have often run into dead ends, like with the recent slowdowns in progress in mechanistic interpretability, or the failures of reductionism in biology.

But there is something else that makes the mechanistic picture especially hard to let go of: the possibility of control. That is the promise that mechanism makes: once you truly have a mechanistic understanding of something, you can interfere with it, disrupt it, reshape it to fit your goals. This is why AI safety researchers care to have a mechanistic understanding of AI systems, so that we can maintain control over them, lest they become too powerful.

To let go of mechanism, then, is to accept that there is a limit to your capacity to control the world. The mechanist believes that reality is a mechanism all the way down, which means that reality can be controlled all the way down. The more we progress in science and technology, the more fully we can control reality to fit exactly to our liking.

I don’t think we can entirely settle this question today, with philosophy – history is replete with both examples of our failure to shape reality to our liking (see every dictator that was toppled, the long list of diseases we have yet to cure, and the fact that we still can’t get computers to work right), but it is also full of feats of control we would not have imagined possible (gene editing, moon landings, and short films made out of individual atoms). We may just have to let the mechanists have their chance at building more technology and see how powerful it makes us. But there is another question I want to leave you with, which might be easier to answer today. What kind of person do you become, when mechanism and control are your operative lens for viewing the world? Is that the kind of person you want to be? And is that the kind of person you want to share a world with?

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’s commonplace now to think of living things as machines. A plant is a machine that converts sunlight, water, and carbon dioxide into oxygen via photosynthesis; an animal is a machine that takes oxygen and food and outputs carbon dioxide and water. While there are parallels between machines and living beings, most people, especially people who primarily work with machines (i.e. engineers), take this analogy too far. There is a crucial difference between the two that is not captured when thinking about inputs and outputs. In living things, unlike in machines, unreliable parts make a reliable whole.

All of us are made of building blocks which have an autonomy of their own, but which nonetheless work together to create an integrated system that functions consistently. Cells, proteins, chemical cascades, and neurons all have an element of chaos to them—they don’t behave in easily predictable ways—and yet your heart beats three billion times, continuously, until you die.

We are unlike machines in that our parts are not reliable: if you give the same neuron the same stimulus, it will not always respond in the same way. We are also unlike machines in that our parts don’t have a perfect fit: people often talk about proteins binding to each other like a “lock and key”, but it’s more like a handshake, where two proteins modify each other’s shape as they interact, connecting based on a level of “binding affinity” that can be higher or lower but never perfect.

It’s hard to overstate just how different this is from an integrated circuit, whose parts are precision-manufactured to fit, and are built for consistency. If you set a bit in a CPU register to a 0 or 1, it will maintain that state with 99.9999% reliability: in fact, the rare time this fails is in the case of cosmic rays causing bit flips. It takes interference from other galaxies to throw the building blocks of computers out of sync, and even that only happens about once every quintillion operations.

The unreliability of biological building blocks is not a bug, it’s a feature. Cells are better thought of as active agents which pursue goals than passive mechanical parts. This means that on the one hand, they are less reliable, because they may sometimes take actions that are misaligned with the goals of the larger system (e.g. cancer). On the other hand, this unreliability comes with a creative flexibility: when one part of the system makes a mistake, another part of the system can step in and compensate. When neurons in your visual cortex are damaged, neighboring neurons can reorganize to take over their function, restoring partial vision. As cells in every part of your body die, other cells come in to take their place. Fault-tolerance is built into every level of the system, because every level of the system is partly unreliable. The unreliability of the lower levels, rather than being a nuisance, can actually be harnessed, like when bacteria increase the amount of randomness in their gene expression when stressed, to increase their odds of survival.

This is the root of the difference between biology and machines, at least in their current form: biology is grown, machines are designed.1 Machines are built by teams of people, and as such they need to be shaped in such a way as to be easily understood and manipulated by teams of people. The principles that apply in an engineering context—separation of concerns, reducing the system down to simple building blocks, each part having a well-defined function, each part being made to be as reliable as possible—apply only partially in biology, forever restrained by the lack of any conscious thinking minds behind the development of life. The world of biology is not a world of easily distinguishable objects and well-defined relationships, the kind you’d find in an architecture diagram. The world of biology is one of interleaving, self-perpetuating, ever-evolving processes.

Ultimately, this difference between organisms and machines, like everything else, is more a matter of degree than a strict binary. There are evolutionary aspects to the development of technology; a software codebase consisting of millions of lines of code is not designed top-down, but emerges bottom-up as thousands of individual engineers contribute to it. The weights in a neural network that powers a chatbot are not “designed”, they are grown as part of a training process, bringing them closer to biology than traditional software.

But there is a useful difference to keep in mind here, which is less the difference between groups of objects (cells vs computers, plants vs cranes), but between mindsets of understanding and design. There is the mechanical mindset – which emphasizes reduction into simple parts and total control over every aspect of the system – and the organismal mindset – which emphasizes creative autonomy over predictability. What we need to be careful about, especially in a society overrun by machines, is letting the mechanical mindset dominate the other. To view predictability and control as the unalloyed good, and to think of randomness as a problem to be eradicated. To forget that resilience emerges not from rigidity but from flexible adaptation. It’s easy to look at our computers and skyscrapers and admire them for their elegance, contrasting them with the messiness of a neural wiring diagram or a biochemical pathway. It’s harder to see the wisdom in nature’s messiness.

Thanks James for feedback on drafts.

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.