Flâneur & Humility

I am about to write an essay about humility. This is already a problem.

The moment you believe you've achieved humility, you haven't. It's like trying to fall asleep. The trying is the thing that prevents it. You lie there thinking, I am falling asleep now. This is me, falling asleep. And then it's 3 AM and you're reading about the Roman Empire on your phone. Why the Roman Empire? I don't know. Nobody knows. It's always the Roman Empire.

The most humble people I know never talk about it. Their actions speak. They don't write essays about humility. They just are humble, quietly, without announcement, the way a tree is tall without mentioning it.

And yet here I am. Writing about humility. Already suspicious. I'm like a fitness influencer eating a donut in his car with the windows up.

But something happened this year that I can't stop thinking about. Writing is how I think. Some people meditate. Some people run. I write things down until they make sense. Usually they don't make sense. But you have to try. You sit there with the words and you move them around like furniture in a room that will never look right.

Nobody teaches you how to be humble, by the way. There's no course. No certification. Huberman has not made a podcast about it, yet. Give it time. Soon there will be a three-hour episode about the neuroscience of humility, with specific supplements. Until then, maybe this essay is just a reminder I'm writing to myself. A yearly check-in. A way of asking: have I started believing my own nonsense again?

You might ask yourself, why is Matin writing about this and why is he going to suddenly switch and talk about cities? It will all make sense, just let me explore this with you. Or it won't make sense. That's also possible. I'm not making any promises here.

I have a theory about cities. A city is not its buildings. It's not even its people, exactly. It's more like a frequency. A watermark. Something that stains you if you're not careful. You don't notice it until you leave. Then you meet people from other places and suddenly you hear yourself. The jargon. The posturing. The certainty about things you don't actually understand. You're at a dinner party in another city and you hear yourself say "product-market fit" and everyone looks at you like you've just spoken in tongues.

I've lived in San Francisco for three years. I have never been to Alcatraz.

Three years. The prison is right there. I can see it from the pier. It's an island. Al Capone was there. I have not gone. Not once. I keep meaning to. Every week I tell myself this is the week. It never is. There's always something more urgent, more important, more aligned with my goals. I also passed the honeymoon phase of my stay in San Francisco, and after that you can't visit those tourist attractions anymore. I'm not sure who came up with this law.

This is unrelated to humility. I just wanted to mention it. The Alcatraz thing bothers me.

Here is what is related to humility: the watermark of San Francisco. I've thought about this a lot. Walked the streets. Took notes. And here's what I found:

Young people trying to impress older people with money. And both sides loving every minute of it.

I once watched a twenty-four-year-old at a coffee shop, holding court with a partner from a well-known fund. The kid was explaining why his startup was going to be bigger than Stripe. Not as big. Bigger. He'd been working on it for four months. Four months. That's not even enough time to get good at making coffee, and this kid is already planning the memoir. He spoke with the certainty of someone who had already built it, sold it, written the memoir, and was now doing a press tour for the movie adaptation.

The partner nodded along, asking softball questions, enjoying the performance. When the kid left, I did not expect anything. And that's exactly what happened. The partner turned to his colleague and said, "I like his energy."

That's the whole game. Confidence is the product. Certainty is the pitch. Humility is nowhere in the room. Humility didn't even get a meeting.

With success comes the temptation to tell oneself a story, to round off the edges, to cut out your lucky breaks and add a certain mythology to it all. You know, that arcing narrative of Herculean struggle for greatness against all odds: sleeping on the floor, being disowned by my parents, suffering for my ambition. It's a type of storytelling in which eventually your talent becomes your identity and your accomplishments become your worth.

And look, it's a good thing that people believe in young people, and this attitude is what makes San Francisco and the United States something special. I'm not against that. To the contrary, it is the reason why I left Europe a few years ago. In Europe, if you tell someone you're starting a company, they look at you like you've announced you're joining a cult. Here, at least people think you might succeed. That optimism is precious.

But I wished the kid had a little more humility. A little more focus on the work and less on the performance. Because watching him talk, I didn't think: I hope this kid wins. I thought: I hope this kid learns something before it's too late. I had to learn that recently. It's eye-opening. It makes you very self-aware. Also very embarrassed about things you said six months ago, but that's part of it.

Y'all spend too much time on captions and not enough time on action.

Humility is not rewarded here. It's seen as a lack of conviction. A gap in your armor. If you're humble in a pitch meeting, people assume you don't believe in your own product. "He seemed uncertain," they'll say. As if uncertainty weren't the most honest response to building something new.

The entire incentive structure rewards the opposite. Social media rewards the opposite. You cannot go viral being humble. You go viral being extraordinary, or pretending to be. We now have Twitter accounts dedicated to mocking the humble-brags of venture capitalists. The fact that these accounts exist tells you everything. They have hundreds of thousands of followers. The content is endless.

A lot of the city is twenty-somethings pitching ideas they found on their X.com feed that morning. Many of them are brilliant and some will change industries. But sometimes you see someone in the back of a Waymo, gliding to the Blue Bottle in South Park, explaining why their "agentic workflow" startup is going to revolutionize housing, and you think: when did we all agree to talk like this? Who decided these were the words?

One of the most important papers of the last few years had the title "Attention Is All You Need." A lot of people looked at that title and took it to heart. They focused everything on that sentence without reading the actual paper. They didn't realize it's a technical document about transformer architecture, written by researchers who dedicated their lives to their craft. It's not a lifestyle philosophy. It's not advice. It's a paper about how machines process language. But try telling that to someone who's made "capturing attention" their entire personality. That's the average twenty year old on Twitter today. We all know the companies and the people.

I should confess something. I was becoming infected by all of this. Slowly influenced without realizing it.

The way you don't notice you're gaining weight until your pants betray you. The way you don't notice you're losing your hair until a photograph betrays you. The way you don't notice your soul leaving your body until you hear yourself say "let's double-click on that" in a conversation about lunch.

"Let's double-click on that." About lunch. About where to eat. I said this. Out loud. To another human being.

I started using the same words. Having the same ideas. Displaying the same unearned confidence. The same arrogance. Everyone in San Francisco is basically a wrapper around Twitter, and I became a wrapper too. A very convincing wrapper. I could talk for twenty minutes about things I'd learned twenty minutes ago. I was a content delivery system for other people's thoughts.

I was losing myself and I didn't even notice. It took time and distance and long stretches of doing absolutely nothing to become aware.

This is the thing about self-awareness: you need it most when you have it least.

Rick Rubin wrote something about this. He said self-awareness is the ability to tune into what we think and how we feel without interference. To notice how we notice the outside world. He said it's the key to making revelatory work. To knowing the difference between pretty good and great.

I had lost that. Completely. San Francisco had uploaded something into me, and it was running in the background, and I couldn't see it because it had also disabled the part of me that could see it. Like malware that deletes your antivirus software. Very sophisticated. Very sneaky.

Then I went to New York. Just a layover.

I don't know how to explain what happened. It was like meeting someone at a party and talking for ten minutes and somehow knowing them better than people you've known for years. The city did something to me. Or maybe it undid something. Uninstalled something. Touching grass, extreme edition. Except it wasn't grass. It was concrete and pigeons and very cold air and the smell of something unidentifiable coming from a subway grate.

I decided to be a flâneur. A flâneur is someone who wanders a city with no plan, just watching. I learned this word from Nassim Taleb. He said: don't be a tourist. Tourists have itineraries. They rush from landmark to landmark with a kind of desperate efficiency, as if the Statue of Liberty might leave if they don't get there by 2 PM. A flâneur has no schedule. A flâneur sits on benches. A flâneur takes notes.

I took notes.

Here is something I wrote on a bench near Washington Square Park: Man arguing with pigeon. Pigeon winning.

Here is another: Woman holding door for stranger. Stranger does not acknowledge. Woman stares at back of stranger's head with look of profound disappointment. This is civilization.

I cannot stress this enough: write it down. That's what makes you a professional flâneur instead of just an amateur flâneur. You have to write it down. Otherwise you're just a guy sitting on a bench. There are a lot of those. The difference is the notebook.

The thing about New York, the thing I noticed almost immediately, is that ambition and humility are not at war there. In San Francisco, they feel like opposing forces. You can have one or the other. Choose. If you're humble, you're not ambitious enough. If you're ambitious, humility is a speed bump. Get it out of the way.

Not everyone thinks like this, but it's what the city screams. And once you're used to what a city screams, it's hard to hear what the city whispers.

In New York, ambition and humility hold hands. They take the subway together.

And everyone takes the subway.

I stood on a platform at 14th Street and looked around. There was a woman in a fur coat. There was a man in paint-covered jeans. There was a teenager with headphones so large they looked architectural. We were all waiting for the same train. It was late. We all accepted this. Nobody was special. The hedge fund manager and the line cook, equal before the MTA. The MTA doesn't care who you are. The MTA doesn't care about anything. The train comes when it comes.

I thought: this is humility. This is what it looks like. It looks like waiting.

The city is so big. You're constantly in touch with reality. You can't Waymo your way out of it. You eat from the same carts as everyone else. You stand on the same platforms. You wait for the same delayed trains. It was also very cold. Maybe that helps. It's hard to be arrogant when you can't feel your face.

I met some people there. Old friends, new friends. They gave me their time, which in New York is the most expensive thing you can give. Time there is not like time in other places. It moves differently. An hour in New York contains more than an hour elsewhere. I don't know the physics of this. I just know it's true. Something about the density, maybe. Or the pizza.

We had conversations. Real ones. The kind where someone says something and you feel it rearrange something inside you. I hadn't had conversations like that in a while. In San Francisco, conversations have a game theory running in the background. There is a deck, somewhere, even if you can't see it. Someone is always calculating, always selling, even if it's just to establish themselves as a person worth knowing.

In New York, we just talked. About nothing and everything. About things that didn't matter and things that did. Nobody was positioning. We were just people, talking. It felt like something I had forgotten was possible.

Someone said to me: "You can be ambitious and humble at the same time. They're not opposites. One is about what you want. The other is about how you carry yourself while wanting it."

I wrote this down. I am looking at it now.

I had never seen ambition and humility coexist before. I didn't know it was possible. San Francisco had convinced me you had to choose. New York showed me that was a lie.

When I was young, actually young, not San Francisco young, which is a different thing, I had a curiosity about the world that felt infinite. Everything was interesting. A bug on the sidewalk. The way light came through a window. The specific sound of rain on different surfaces. Rain on a tin roof versus rain on leaves versus rain on a car. All different. All worth noticing.

Somewhere around eighteen, this started to fade. Life has a way of corroding that curiosity. Corrupting it. It happens so slowly you don't notice. And then one day you're explaining agentic interfaces to someone and you realize: I have become a person who explains agentic interfaces to people. When did this happen? Who authorized this?

The arrogance crept in. The certainty. The performing. And it pushed out the curiosity. There wasn't room for both. You can't be curious if you already know everything. You can't learn if you're too busy teaching.

If you start believing in your greatness, it is the death of your creativity.

I want to protect what's left of that kid. The one who found everything interesting. The one who didn't know enough to be arrogant about anything. The one who asked questions instead of giving answers. If I can do that, protect that curiosity, stay humble enough to keep learning, maybe when I'm eighty I'll look back and feel grateful. Not just for the life I had, but for the lives I was able to change along the way.

I know, I know. Everyone seems to have a clear idea of how other people should lead their lives, but none about his or her own. That's the joke. That's always the joke.

So I'm taking some time off. A month. Quiet work. Long walks. No decks. No "agentic interfaces." I'm uninstalling whatever San Francisco uploaded into me. It's taking longer than I expected. The software is persistent. It keeps trying to reinstall itself. I'll be walking in nature and suddenly catch myself composing a tweet in my head. About the nature. About how profound the nature is. About what the nature means for the future of AI.

A wise young man told me recently: sometimes to move forward, you have to step back. Re-evaluate. Look around. Breathe.

So that's it. That's the biggest lesson I learned this year. No ambition without humility. Five words. It took me three years in San Francisco, a day in New York, and several thousand words in this essay to arrive at five words. This is either very inefficient or very human. Probably both.

The most humble people don't talk about it. Their actions speak. And here I am, talking about it. Several thousand words about not talking about it. I am aware of the irony. The irony is not lost on me. The irony is very much found.

But maybe that's okay. Maybe the first step to humility is admitting you don't have it. Admitting you lost it. Admitting you became a wrapper around Twitter without noticing. Admitting you were losing yourself and didn't even wave goodbye.

Self-awareness is the beginning. You have to see the problem before you can fix it. You have to hear yourself, really hear yourself, before you can change what you're saying.

I heard myself this year. Finally. And I didn't like what I heard.

So now I'm changing it. Slowly. The way you lose weight. The way you fall asleep. Not by trying, but by creating the conditions and then letting it happen.

Stay humble. Protect your curiosity. Take the subway with everyone else.

Write it down.

Acknowledgements & Disclaimers

I'd like to thank the people who listened to me figure this out in real time: Long, Evan, Soleio, Lukas, Shaad, Ron, Frank, Luke, Liam, Dylan, Dara, and Sam, Max, Coleman, Matt, Austin, Todd, Eric, David, Jeffrey, Sobhan, Spencer, Jack, Rich. Some of you probably didn't realize you were helping. You were.