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Welcome to My Site!

My Book

I wrote a book, Peculiar: Lessons from Amazon’s Leadership Principles! Most companies want to be like Amazon but can’t figure out why their attempts fall short. My book pulls back the curtain on how Amazon actually works — from the Leadership Principles that drive its culture to the business wisdom you can apply anywhere. Peculiar is a practical, human, and humorous guide to one of the world’s most fascinating companies.
Buy it at Amazon.

My Substack

I’ve created a Substack newsletter, AI for Poets, about using AI to be more human. It’s not about mastering the tools or keeping up with the hype. Rather, it’s about what happens when you actually sit down and play with AI, and what it reveals about language, creativity, and how we think. Come explore with me.
Subscribe at aiforpoets.substack.com.

About Me

I’m a devoted husband and father to an awesome family. For work, I’m currently an Executive Director at JP Morgan Chase focusing on internal tools to help our technology organization be more effective. I’m a Product Manager who looks at the goals of the business and uses technology to deliver those business and customer goals. In the past, I’ve driven transformational change at Citi, AIG, and Amazon Web Services. For more information about what I do at work, please visit my LinkedIn profile.

My Blog

I collect stories. There are so many amazing things happening every day. I need to spend some time writing them down before they slip away. Some of these ideas are so powerful that they hit me like a bolt of lightning. It’s my job to capture that lighting and put it in a bottle to share it with you. I want to capture that feeling that Archimedes had when he had an insight sitting in the bathtub screamed “Eureka!” and ran naked down the street. I know that I’ll rarely if ever make it there, but that won’t keep me from trying!

Here’s some of my latest posts:

And here are some of my posts about AI and ChatGPT:

Blog Highlights

Here are some highlights from 2024

One of my favorite topics for the last few years is writing about AI. I explored it from a number of different perspectives:

ChatGPT has helped me quickly turn ideas into complete blog posts and respond in real-time to things I’ve encountered. This year, it made it easier to explore a range of interesting topics like:

With ChatGPT, I learned to capture the small, wonderful moments of my life in writing. It’s like catching a lightning bug in a jar—preserving fleeting beauty to reflect on later. I was able to write about appreciating the sunrisevisiting a classic movie theatre owned by Netflix, and how to turn a nighttime drive into a light show.

Finally, I spent some time writing about self-improvement. Some of my favorite pieces were about the importance of asking for help and practicing self-control. Surprisingly, I even learned a valuable lesson about communication from AI—it’s programmed to respond with honesty, helpfulness, and harmlessness, qualities we humans could aspire to as well.

My Virtual Library

I wanted a place to put all the stuff I think is awesome. Growing up, I always wanted to have a great library in my house. I remembered the excitement when I learned that I could buy the entire collection of The New Yorker in bound volumes and put them in my house. I’d imagined that I would collect great encyclopedias from the past to peruse whenever I pleased. They would live in mahogany bookcases that looked like they’d belonged to JP Morgan. Then I realized that a New York City apartment doesn’t have the space for a physical library. So I did the next best thing. I’ve created a virtual library that includes lots of the things I enjoy, like my favorite books, words, and humor. You can check it out on the menu at the top of the page.

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Marcel Duchamp, the Funniest Man in the Museum

I have always liked art that made me laugh. For years my favorite art joke was René Magritte’s pipe, the painting of a perfectly ordinary pipe with the words “Ceci n’est pas une pipe” written underneath. This is not a pipe. And of course it is not. It is a painting of a pipe. You cannot smoke it. The joke is that the image of a thing is not the thing, and Magritte makes you laugh your way into a genuinely slippery idea about representation.

René Magritte, The Treachery of Images (This Is Not a Pipe), 1929. Los Angeles County Museum of Art. View at LACMA

But I have a new contender for the most absurd and most canonical art joke ever made. Marcel Duchamp took a cheap postcard reproduction of the Mona Lisa and drew a mustache and a little goatee on her. That alone is funny, defacing the most worshipped painting on earth with a doodle. But the title is the better joke. He called it “L.H.O.O.Q.” Read those five letters aloud in French and they spell out the phrase “elle a chaud au cul,” which translates as “she has a hot ass.” He vandalized the most famous face in art and catcalled her. It’s one of the most important works.

Marcel Duchamp, L.H.O.O.Q., 1919.
View at the Norton Simon Museum

Truly good conceptual art is often funny because it’s creating an entirely different point of view. A good joke pokes at something we take for granted and holds it up at a strange angle. The idea of art, what counts as art and what does not, is not something we normally examine. We just walk into a museum and assume the question is settled. Humor is one of the few tools sharp enough to pry it back open.

I went to the Duchamp show at the MoMA recently and spent most of it laughing, which is something that doesn’t normally happen at this museum. Museums, especially a place like MoMA, are about learning and being serious. They are not really set up for fun. Duchamp gave me fun anyway, and the more I looked the more I understood that he was one of the cleverest minds the art world has ever produced, a genuinely brilliant artist in a way that most artists, even very good ones, simply are not.

There is a photo from this trip I am going to use in my holiday letter. It is my mother-in-law Jeanne and me, standing in front of a urinal and smiling broadly. But this wasn’t any urinal. This was THE urinal. Duchamp’s Fountain, the porcelain one he bought in 1917, tipped onto its back, signed with the fake name “R. Mutt,” and submitted to an art exhibition as a sculpture.

Here is the thing. I never actually knew much about Duchamp. I knew about the urinal, of course. Everybody knows about the urinal. But I did not know much else, and what surprised me first was the most basic fact of all. Duchamp could really paint. As a teenager he made the kind of careful, pretty pictures that get a fifteen-year-old praised by his teachers. By his twenties he was deep into Cubism, and then he painted “Nude Descending a Staircase,” which scandalized people who showed up expecting a nude and got what looked like a robot falling down some stairs. He could have spent forty years being a respected painter. Instead he put the brush down and started asking a much deeper question about art. What if the idea is the art, and the object is almost beside the point?

You can see him chewing on that question even in the paintings. His last painting on canvas is a long, strange picture with a painted tear running down it, and over the tear he stuck real safety pins, as if the canvas had ripped and somebody had mended it with whatever was in the kitchen drawer. He also brought in a commercial sign painter to add a pointing hand, and then had the sign painter sign that part of the work. So the painting is partly painted by a hired tradesman who gets his own credit on the canvas. It is a painting that quietly mocks the idea of the painting, and it already has the readymade idea hiding inside it.

Marcel Duchamp, Tu m’, 1918.
Image from Moma of Painting from Yale University Art Gallery

That idea ran through everything he did next. He would take an ordinary manufactured thing, a snow shovel, a bottle rack, a urinal, give it a title, and declare it art. No carving, no painting, no technique. The work was the decision. You can feel the establishment recoiling, and you can almost hear him asking, sweetly, “why not?” If you stand in front of Fountain and find yourself saying “that is not art,” congratulations, you’re participating in the conversation that Duchamp wants to have with you.

And that was the plan from the start. When he submitted “Fountain” in 1917, it went to an exhibition that had promised to show every work that was entered, no jury, no rejections. They rejected it anyway. They hid it during the show and refused to display it, which is precisely the reaction Duchamp was fishing for. He had not made a urinal beautiful. He had set a trap. He wanted the gatekeepers to look at an ordinary object he had chosen and called art, and to blurt out “no, that is not art,” so that everyone would suddenly have to ask the question out loud. What is art? Who decides? The rejection did not ruin the piece. The rejection completed it.

Including these readymades in the MoMA show was difficult. The show has a whole room of them, and almost none of them are originals. They are copies, replicas Duchamp authorized decades later. The reason is simple and a little wonderful. When he first made these things he was an impudent young man, around thirty, and nobody thought any of it mattered, including the people closest to him. The original Fountain was lost. The first bottle rack and bicycle wheel got thrown out, in some cases by his own family doing the sensible thing with what looked like junk. So the artworks that detonated the twentieth century survive mostly as second and third versions, made later, once the world had decided the joke was important after all. There is something perfect about that. The objects weren’t the point, the ideas were.

He kept finding new ways to create transgressive art. He invented an alter ego, a woman named Rrose Sélavy, and had the famous photographer Man Ray take pictures of him in character. The name is a pun. Say it in French and it sounds like “Eros, c’est la vie,” love is life. So the joke runs at least three layers deep, the costume, the name, and the wordplay hiding inside the name, and he is doing all of it with a completely straight face.

When he was escaping from Europe from the war he created the most beautiful miniature copies of his art. For his museum in a box project, he made little suitcases packed with tiny reproductions of his own work, a portable one-man retrospective you could carry around like a salesman’s sample case. And the miniatures are genuinely beautiful, made with real care. The audacity is the timing. He was assembling his own retrospective before he had really had the exhibitions that would earn one. He was curating his own legacy as a joke and as a fact in the same gesture.

When we look at someone like Duchamp now, we tend to see him through the people who came after, the ones who took his moves and turned them into a familiar, almost ordinary kind of art. Stand in front of a urinal in a gallery and it is easy to think of Andy Warhol and the soup cans. But Warhol never makes the soup cans without Duchamp going first. The imitators arrive and copy the discovery so many times that many of us never fully understand it. What was once revolutionary becomes wallpaper.

Jeanette Winterson, in her book Art Objects, writes that “The most conservative and least interested person will probably tell you that he or she likes Constable. But would our stalwart have liked Constable in 1824 when he exhibited at the Paris Salon and caused a riot? . . . To the average eye, now, Constable is a pretty landscape painter, not a revolutionary who daubed bright color against bright color ungraded by chiaroscuro. We have had 150 years to get used to the man who turned his back on the studio picture, took his easel outdoors and painted in a rapture of light. It is easy to copy Constable. It was not easy to be Constable.”

Duchamp was a real philosopher of art, sitting alongside the other brilliant minds who have changed how we see, and he did his philosophy through transgression. Plenty of people are funny. Cartoonists are funny, comedians are funny, the person who first drew a mustache on a poster was funny. Duchamp went much further than funny. He used the joke the way a philosopher uses a thought experiment, to corner you into a question you cannot wriggle out of. When Wittgenstein asks what we really mean by a word, or Descartes asks how he can be sure he is not dreaming, the move is the same one Duchamp makes when he sets a urinal on a pedestal. Each of them takes something you thought was obvious and shows you that you never actually examined it. The urinal is an argument. So is the mustache. He just made his arguments out of porcelain and pencil instead of prose.

That is the heart of it, I think. Art is supposed to surprise you and then make you think, and Duchamp understood that a good joke does both at once, faster than any sermon. He spent a whole career proving that the most serious idea in the room can walk in wearing a clown nose. Jeanne and I have the photo to prove we fell for it, grinning in front of the most famous toilet in the world.

Note: I came across a piece (which I haven’t read yet) that seems similar.

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Uncategorized

The Dizziness of Freedom

I played weekend soccer in elementary school. Though I was far from the best player on the team, I was the fastest kid on the field. That meant I’d sometimes end up on a breakaway, with the ball at my feet and no defenders ahead of me. When that happened, I’d fall down. I’d literally laugh and fall down, and I wouldn’t even try to kick.

Now, decades later, I realized what I was doing. My body was sabotaging itself. The laugh came first, then the legs going soft, then the grass.

This was a reflex. If I had thought about it, I would have had plenty of options. I could have practiced it, until my body knew what to do when the moment came in a real game. But I wasn’t thinking. Underneath the not-thinking was a fear I couldn’t have named at the time. It was a fear of making a decision, and possibly failing.

I thought I didn’t deserve to score. That was the fear underneath, and the usual advice only made it worse. “Fake it till you make it” sounded selfish, a way of saying “I don’t know what I’m doing, so please bear with me while I figure things out.” But the real selfish act is sitting with your own insecurity so long that you forget there’s a job in front of you that needs doing.

Alfred Adler, the great psychologist from the early 20th century, had a word for how to think about this: Gemeinschaftsgefühl. It’s a German word that loosely translates to “community feeling.” The idea is that we’re here to contribute to something larger than ourselves. We are here for the benefit of others, not ourselves.

I have one friend who’s genuinely curious and warm, and asks people good questions. But when a conversation gets into really interesting territory, where something ambiguous or tender is sitting on the table, she laughs. She’s laughing because it’s funny and interesting to her, and also a little uncomfortable. The laugh shuts the conversation down right when it’s getting good. She doesn’t mean it that way, but the laugh does the work of closing a door.

I recognize this because I do versions of it myself. My adult version of the soccer fall is gratitude, both giving and receiving. If someone thanks me for something that actually mattered, I feel the reflex start up. I’ll crack a joke or shift the credit to someone else before the moment can land. Giving it is almost as hard. When I want to tell someone what they’ve meant to me, I can feel my body trying to find a lighter, safer version that won’t require me to sit in the fullness of what I actually mean.

The Danish philosopher Søren Kierkegaard had a name for this reflex. Writing in the 1840s, he was one of the first people to treat anxiety as a philosophical problem. He’s sometimes called the father of existentialism, and what he named was existential anxiety, the dizziness of freedom. It’s the intense uncertainty that hits you when you realize the next move is yours, and so is whatever comes of it. That dizziness is terrifying enough that we spend most of our lives trying to avoid this responsibility.

This matters more as I get more senior at work, where people look up to me. Authenticity matters when you’re a leader, because other people are depending on you. The temptation is to talk about the problems rather than trust the company strategy. But that’s its own kind of falling down in the grass. Part of the job is putting on a brave face even when you’re not confident. Your job isn’t to feel brave. It’s to give other people the steadiness they need.

One of my mentors, a former CEO of several companies, told me once, “You don’t have enough time to be an expert in everything. You do it a couple of times and then move on to something new.” It wasn’t advice so much as access. He was showing me that even at his level, he hadn’t figured everything out. Nobody does. There’s no moment when someone tells you that you’re allowed to take the next step. You grab it anyway.

Now I have the chance to do that for other people, and it’s become one of the best parts of my job. Someone I worked with, I’ll call her Nancy, was very competent but had spent a decade without a real chance to grow. She didn’t feel worthy of the space she was taking up. We worked on small things together, starting with how she introduced herself in a meeting. It was a tiny thing, but it was the same kind of muscle memory I needed on the soccer field. I could stand with her as a coach while she did the work.

Immanuel Kant, one of the great moral philosophers of the Enlightenment, wrote that we stay children, and not because we lack reason. We have the reason. What we lack is the resolution and courage to use it without someone else directing us.

Being an adult doesn’t mean the dizziness goes away. It means you learn to manage it. You stop waiting to feel ready and start. I came across a phrase from the Disordered podcast that sums up this whole essay. The hosts were talking about clinical anxiety, but it applies to existential anxiety too. They call it shortening the time between “oh my god” and “oh well.”

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Life Lessons

The Navy SEAL in Seat 14B

SEAL Team 5 Challenge Coin

On the value of trading things you can’t buy.

I was flying out to California last week for the Collaborative Gain conference and ended up next to a guy who was actually reading. He wasn’t scrolling or multitasking. He was on a Kindle, deep in his book, and stayed that way for a long time. He looked about thirty. That kind of focus is rare enough to make me take notice, like a the way a startup CEO might be wearing a hoodie and a Rolex.

So I did what I usually do when something interesting is sitting three inches to my right. I waited for a natural break and asked him about the book. It was a novel, and he seemed a little embarrassed to be reading fiction. I figured out why when I asked him what he did. He’s a Navy SEAL.

Turning thirty, eight years in, Team 5, based in Coronado just south of San Diego, which turns out to be one of the two main bases for SEALs in the country. The way he talked about it was very matter-of-fact, the way a plumber might tell you he does mostly commercial work these days. He loved his job and he loved his teammates, though he couldn’t tell me anything about what he actually did.

He went to the Merchant Marine Academy and met his wife there. She’s still a Merchant Marine. He did ROTC and was on track to be a commissioned officer, then realized that if he actually wanted to be a SEAL, he had to give up the officer track and enlist. He also liked the idea of picking up specific skills, or quals as the SEALs call them. One of his favorite quals was as a SEAL medic, battlefield doctor.

Now he’s applying to Navy med school. The Navy has a program where they run you through a two-year pre-med, then send you through med school, then you do your residency as a Navy doctor. Add that to the eight years he’s already done and the time on the other side, and he hits a twenty-year pension right around the time he finishes residency. He’ll walk out as a doctor with a pension.

I asked him what kind of medicine. He said, “Anesthesiology would be the smart move, but I kind of want to be a trauma surgeon.” I said something about trauma surgery being brutal, long hours, not the money of the quieter specialties. He shrugged, and said, “Yeah, but I’ve got an ego. I’m a SEAL.” He knew it was just his ego talking, and was probably going to go with anesthesiology.

Trauma surgery and anesthesiology seemed like such different things, but to him they were pretty similar. Trauma surgery was easier than you’d think because it’s like battlefield surgery with no one shooting at you. He was impressed with battlefield anesthesiology, because those guys have to intubate someone who’s just been blown up. I asked about the residency part, the famous thirty-six-hour shifts. When was the last time he’d been up for twenty-four hours straight? He said, “Friday. I was up until four to finish a qual and then took a flight at seven.” That thing med students find crushing and horrible, he does it for fun on a weekend.

At some point I realized that he might have a challenge coin. My son Blake and I collect challenge coins. We pick them up during Fleet Week at the Intrepid, and it’s become a small family thing we do together. I even have one from a space launch. So I told him about our family project. He rifled through his bag for a minute with a half smile on his face, and pulled out a SEAL Team 5 coin. The actual handoff was awkward on my end. He tried to pass the coin to me, and I blanked on how this is supposed to work, which is palm-to-palm during a handshake, the coin pressed discreetly into the other person’s hand. He handled it gracefully and gave it to me again, this time with the handshake, the way it’s meant to go. There’s something I love about that tradition, the idea that a coin carries a unit’s history and you hand it to someone as a kind of keepsake for the experience behind it.

I had a few copies of my book in my carry-on to sell. I gave him one. He tried to wave it off and told me I should keep it if I needed it, that he was happy to give me the coin anyway. I told him no, this was the fun part. We’d both just handed over something we were proud of, something we’d earned. His coin took eight years of service. My book took five years of evenings and weekends. Neither one was the kind of thing you could buy.

I’d spent the whole flight being amazed by this guy. The focus, the career, the quals, the staying up until four on a Friday because that’s just how the week went. Everything about his life was something I couldn’t comprehend doing. And then I was standing there holding his coin, and he was standing there holding my book, and it hit me that the admiration ran both ways.

He reads fiction because he just can’t get into non-fiction. He told me his living room has a giant bookcase, and he only puts books on it that he actually loves. If he reads something on his Kindle and it matters to him, he buys the physical copy to put on the shelf. He took a non-fiction book from a stranger on a plane and was genuinely glad to have it. I can’t be a SEAL. He can’t write a book. We’d each spent years making something the other person couldn’t make, and for a couple of hours over the middle of the country, we happened to be sitting close enough to trade.

We took a picture after we got off the flight. Me holding the coin, him holding the book. I’ll keep that one to myself, because posting a photo of an active SEAL online seems like exactly the kind of thing a SEAL would prefer I not do. I’ll admit I also took a surreptitious shot earlier in the flight, which in retrospect was an extremely stupid move. The man is a trained operator whose professional skill set includes noticing things, and if he’d caught me and cared… well let’s be thankful he’s such a nice guy.

If you want to learn more about challenge coins and the traditions behind them, 99% Invisible did a great episode on the subject.

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Uncategorized

Mind Like Water

David Allen wrote Getting Things Done in 2001 and became a kind of secular priest for ambitious, overwhelmed professionals. His central claim was almost absurdly simple. Get things out of your head and write them down. He wasn’t just pitching better organization. He was promising you’d feel calmer, think more clearly, and be more present with the people around you. He called the result “a mind like water.”

When I first heard this, I was drowning in work. I tried it, and it made me more relaxed. But I kept wondering why making lists made me feel better. The answer is a simple principle called the Zeigarnik Effect.

Bluma Zeigarnik was a Soviet psychologist. In the 1920s, she was sitting in a Berlin café when she noticed something odd about the waiters. They could hold an absurdly complicated order in their heads while it was still open (twelve people, substitutions, dietary restrictions) and then forget it almost instantly once the bill was paid. She went back to her lab and confirmed what she suspected. We remember unfinished tasks far better than finished ones. The brain treats incomplete work like an open file on your desktop, staying active and demanding attention until it gets saved or closed.

Maria Ovsiankina noticed something similar. Open loops don’t just stay active in memory. We also feel a strong pull to return to them. The Ovsiankina Effect is why it’s so hard to stop in the middle of something once you’re engaged, and why interruptions feel so grating even when they’re minor. We remember the open loop and feel compelled to close it.

And that’s what I notice in myself. Whenever I start a new project, pick up a new book, or start a new text conversation, that’s a new open loop. Often these unfinished things would scream, “Hey! Look at me!” By the end of a busy day, the tiredness I feel isn’t just physical. Every loop I opened and didn’t close is still there, demanding to be dealt with until I do something about them.

That’s why I could get a mind like water just by writing things down. Writing something down closes the loop for a while. My mind can stop circling. The list holds my open loops so my attention doesn’t have to.

The most obvious thing I learned is that the number of open loops matters. Right now I’m reading a book I actually want to finish, and every instinct says to start the other one on my shelf. But if I do, I’ve just added another loop pulling at me from somewhere I can’t quite see. If I really want to finish the first book, the answer is to wait. I’ve made a commitment to the first one, and splitting the loop makes both harder. In the end, the answer is to close some loops before opening new ones.1

When I’m in the middle of something I love, the open loop isn’t a burden. Everything is in alignment, like a brigade of tiny soldiers who were all wandering in different directions suddenly snapping into formation and marching together. My mind is going to be obsessed with this thing anyway. It becomes the single most important thing in the world, and if I do anything else, it’ll just be a distraction. It’s what keeps me thinking about it in the shower, wanting to talk to everyone about it, working on it the moment I have ten free minutes. I’m in a flow state, and the incompleteness is what keeps it going. Then, when the loop finally closes, everything settles into a beautiful harmony—at least for a little while. When I finish a book, it becomes a memory, which is why I try to write about books while I’m still in the middle of them.

The thing I keep coming back to is how much better everything feels when I’m actually inside one thing. Not managing ten things, not half-finishing six of them, just present with one open loop that I care about. I’m trying to keep the loops few and stay inside the good ones. That’s as close to a mind like water as I’ve managed to get.

Footnotes

  1. Software engineering calls this keeping your Work in Progress (WIP) low so one project doesn’t distract from the others. ↩︎
Categories
Life Lessons

The Art of Getting Out of the Way

There’s this thing that happens on crowded sidewalks in New York. Two people are walking toward each other in a rush, both trying to navigate around the other. One steps left, the other steps left. One corrects right, the other corrects right. And suddenly you’re doing this little dance with a stranger, each of you making it worse by trying to fix it.

I heard something recently that reframed the whole thing for me. The problem isn’t that people are clumsy or oblivious. The problem is that two people are both trying to control the same thing at the same time. Both are trying to help. And it creates a gridlock where they both end up blocking each other. One of them has to let go.

So instead of trying to solve the problem and evading the other person, I tried something different. I started doing nothing. I slow down slightly and let the other person choose. They make a move, I follow, and we’re past each other in a second. The hard part is that slowing down feels wrong. Every instinct says to move, to fix it, to be the one who figures it out. Standing there, barely moving, while someone walks toward you feels almost rude. But that discomfort is the whole point. The moment I stop trying to solve it, it solves itself.

And the failure mode, the case where both people let the other choose, seems like it would be horrible—no one would move. But actually it’s fine. We drift past each other slowly, a little awkwardly, and nothing bad happens. No collision, no real delay. The worst outcome of doing less turns out to be pretty manageable.

But it’s not just about sidewalks. I was talking to a friend recently who said, half-joking, that he needed to do less. He meant it as a complaint about being overloaded. I took it as a goal.

Oliver Burkeman makes a version of this argument in Meditations for Mortals. He pushes back on the idea that importance and difficulty are the same thing, that if something matters it should feel hard, and that easy means you’re not really trying. He offers a different question: what if this were easy? Not as a feel-good slogan, but as a way of living. What if you built your life so that the default was things that felt natural and really wanted, and the hard stuff was something you looked at deliberately and decided was worth doing.

I’ve been trying to live this way. I’m doing less and holding things more loosely. I’m noticing when I’m doing that sidewalk dance inside my own head, overcorrecting, making things harder than they need to be. The goal isn’t to stop caring. It’s to stop treating caring and straining as if they’re the same thing. When I’m doing something because I want to, I’m better at it. Not because I’m more focused or disciplined, but because I’m not fighting myself the whole time.

Getting out of the way is a skill. Whether it’s on the sidewalk or in my own head, I’m still learning it.

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ChatGPT Fun Stuff New York City

The Great Thaw

“What were you most excited about when you thought about coming to New York?” I asked.

“The snow,” she said. “Growing up in Singapore, I’d always see movies of the snow, but I’d never seen it in person. Tbe snow is always this beautiful white blanket that comes out and coats everything.”

“What disappointed you most about New York?” I said.

“Right after it snows, it turns into this big brown mush the next day.”

That’s how New York winters work. We get a whole lot of snow. It turns to mushy brown slop. Then it melts and goes away.

A Classic Brown Post Snow New York Day

Except for this year.

This year, the snow fell and stayed. Not for a day or two, but for weeks. It piled up on the sides of the sidewalks and just sat there, like big white bumpers at the bowling alley. This is the type of thing that happens in places like Toronto. When we visited my sister early this year, I was surprised to see construction happening while it was snowing—because in Toronto in the winter, it’s always snowing.

It wasn’t just New York. Dallas closed schools for four days due to snow. Schools closed in Columbus and Chicago due to the cold. When the wind chill is -25 or below, schools close because it is simply too dangerous to walk to school or wait for a bus. The National Weather Service called one stretch of it an “epic, generational arctic outbreak.” Two hundred million people across the country were under some kind of cold-weather advisory at one point.

This was a real winter, the kind you see on ski mountains.

When it started to melt, this was like nothing I’d ever experienced. The closest reference point I had was the Great Thaw in the movie Frozen. In Scandinavia, where Frozen came from, the winter melt is a big thing. The winters there are long and genuinely dark, months where the sun barely shows up and the cold is something you live inside rather than pass through. Before Christianity arrived, Norse communities celebrated Dísablót, a festival marking the transition out of winter, a collective acknowledgment that the dark season was ending.

That’s what this felt like when the snow started to melt.

So I started taking pictures. I got some good ones, but I couldn’t really capture that feeling. What I really wanted was a time-lapse of the snow melting, and that wasn’t going to happen with my camera alone.

So I used Grok. I took an initial picture and told it what I wanted: “A time-lapse photograph of the snow melting throughout the day.” I had an image in my head of what that thaw looked like, the feeling of it, and I wanted to show someone else. I didn’t want to document the thaw. I wanted to express it. Grok gave me that, more or less, with a few gloriously wrong attempts along the way that you’ll see below.

There isn’t really a better tool for that right now.

The Great Thaw

The AI blooper reel is below.

There’s a surprising amount of water when the snow melts
The train station disappears halfway through the video.
Categories
Uncategorized

The Massage Convert

For many years, I’ve been wrong about massages.

My mistake was that I thought about them scientifically. If it’s worth doing, there should be measurable outcomes. Deep tissue work releases lactic acid. Pressure on trigger points reduces inflammation.

That didn’t work for me. It just hurt, and then hurt a little less, and the whole thing felt expensive and strange and not worth it.

What changed wasn’t the massages. It was me getting better at relaxing. And once I stopped bracing against the whole experience, I started to understand what it actually is.

It’s not a medical procedure. It’s something much more human than that.

Think about the moments when you truly feel pampered. Not just served, but genuinely attended to. A great meal where the waiter anticipates what you need before you ask. A barber who takes their time. A tailor making small adjustments with real care. Another person giving you their full attention, and something in you settling because of it.

A massage is that, taken to its logical extreme. You lie there and surrender completely. Someone spends an hour doing nothing but tending to you, figuring out where you’re tight and working on it. And then there are the oils.

Across every tradition that ever tried to heal the human body, Ayurvedic practice in India, Egyptian medicine, Greek and Roman bodywork, Traditional Chinese Medicine, you find oils. Warm substance applied to skin. The specifics differ. The impulse is identical. Cultures with no contact with each other, no shared language, no reason to coordinate, all arrived at the same answer. That’s not coincidence. That’s something true about what a human body needs from another human body.

There’s a ritual to all of it. The quiet room. The dedicated hour. The ancient map the practitioner is working from. This architecture isn’t decoration — research into how healing works suggests the more ceremonial and physical an intervention, the more powerfully it works. The body registers: something significant is happening here. And it opens.

Acupuncture is a great example of something working even though it’s not supposed to. The studies are genuinely mixed — some show it works, some show that sham acupuncture, needles placed nowhere near the traditional meridian points, works just as well. The scientific community mostly reads that as debunking. But there’s another interpretation sitting right there: maybe the ritual is the mechanism. The needles, the serious attention to your body, the quiet room — maybe that’s what’s doing the work. If sham acupuncture works too, that’s not proof that acupuncture is fake. That’s proof that the ritual is so powerful it doesn’t even need to get the details right.

Reiki takes it even further. It’s a Japanese healing practice where a practitioner places their hands lightly on or just above your body, working with what they describe as life energy. No needles, no oils, no manipulation of tissue. Just presence and intention and the belief that attention itself can do something. Reiki shouldn’t work by any measure. No physical contact, no chemical intervention, nothing you can point to. Which makes it the purest version of the argument. It can’t possibly work through scienc,e yet it still produces results. So it’s probably not the science doing the work here.

I was making the same mistake with massage. Focused on whether it worked, whether it was worth it, whether Vladimir was hitting the right spots. Missing the whole point. The massage didn’t change. I did. I got out of the way of something that was always going to work.

Why did every human culture, independently, land on the same answer? Ayurveda. Egyptian medicine. Traditional Chinese Medicine. Greek bodywork. All of them. Oils, hands, ritual, presence. One person anointing another and saying: for the next hour, this is all I’m doing. Because it works. That’s the whole argument. I get it now. Took me long enough.

Categories
Judaism Uncategorized

Profaning the Sacred

Apologies for posting this on a nonstandard day, but I wanted to post this in time for January 27th, Holocaust Remembrance Day.

The remains of the fire that tore through Beth Israel Congregation, the only synagogue in Jackson, Mississippi in January 2026. 

I’ve been thinking about Kristallnacht—the Night of Broken Glass. It’s a strangely beautiful name for such horror, and the word has actually fallen out of favor in Germany, where people now recognize it as a euphemism that downplays the violence and brutality of the pogroms. They prefer alternative names: Novemberpogrome (November Pogroms) or Reichspogromnacht (Reich Pogrom Night). These names capture the truth more honestly—violence, desecration, a turning point.

A few years ago, listening to a survivor speak at our synagogue, something struck me about that night. Not just its historical significance, but something more fundamental about the nature of evil itself.

The Banality of Evil

The woman who spoke was quite old. She had been a child during Kristallnacht, which means we’re approaching the end of an era when people who actually experienced the Holocaust can speak on their own behalf. Once they’re gone, these events become history—easier to file away, easier to forget the ordinary horror of it all.

She described how people came into synagogues and desecrated the Torah. Synagogues were torched. Torah scrolls were ripped and trampled. Cemeteries were defiled. Jewish books were burned. Jewish men were rounded up and sent to concentration camps.

We like to think that if we had been there, we would have known. We would have seen the evil clearly and stood against it. We imagine we could have explained things to people, made them understand. But the reality is that evil is far more banal than that. It doesn’t always announce itself with horns and pitchforks. It begins quietly, by gradually stripping away their humanity, and what better way of destroying their humanity than destroying the things they hold most sacred?

That’s why the desecration of the Torah hit me particularly hard that day.

From Sacred to Profane

The word “profane” originally means to make something ordinary, to strip away its holiness. I thought about my son when he was two years old, trying to climb into the ark that stores the Torah scrolls in our synagogue. To him, it was just a cabinet—an object with its profane, functional purpose. But to us, it’s sacred space, the holder of our most important text, our connection to thousands of years of tradition and meaning.

Profane also means to violate or treat with contempt. That’s what happened during the Jewish pogrom that night—the systematic profaning of sacred objects, the desecration of things that held deep meaning for an entire people.

When they destroyed the Torah scrolls on Kristallnacht, it wasn’t simply about destroying Judaism or trying to destroy the Jews. When you destroy the sacred objects of a people you’re ripping away their humanity. Once you do that, you can do whatever horrible thing you want to them, because these people are no longer human in your eyes. They’re objects. Worse than objects, actually—they look like humans but you’ve decided they’re not. That’s why the Nazis could do all of these horrible things to the Jews—because we were no longer human.

Where are We Now

Dara Horn captures something devastating in her Atlantic article Is Holocaust Education Making Anti-Semitism Worse? She writes that Holocaust education treats Jewish murder as a universal metaphor instead of honoring Jews who died. The dead Jews of the Holocaust are being used to teach a general lesson on tolerance and genocide—profaning their memories.

She points out that the National Museum of African American History doesn’t end its slavery exhibition by pivoting to “other enslaved peoples throughout history.” That would be insulting. But Holocaust museums routinely do this to Jews, ending with other genocides and generic “upstander” pledges. Jewish experience becomes a metaphor, never something valued for its own sake.

While we talk about the atrocities of the Holocaust, students make “Jew jokes” without stigma. People throw pennies at Jews in 21st-century America. Shopping carts “accidentally” ram someone wearing a kippah. When you set the bar for bigotry at mass murder, most of it doesn’t make the cut.

David Baddiel captures the double standard in Jews Don’t Count. We’ve created a hierarchy of protected minorities, and Jews don’t make the list. Whoopi Goldberg can say the Holocaust “wasn’t about race”—just “white people doing it to white people”—as if Jewish identity doesn’t count. “What should we do about Israel?” has become the new “What should we do about the Jews?” The rhetoric around Israeli “misdeeds against humanitarianism” is eerily similar to the Nazis’ reliance on science—different vocabulary, same structure.

When those men desecrated the Torah scrolls on Kristallnacht, they stripped away Jewish humanity by profaning the sacred. We can’t just teach people about gas chambers and expect them to recognize anti-Semitism—yet that’s exactly what we’re doing. Holocaust education has trained a generation of “upstanders” who will spring into action the moment they see another Holocaust—and do nothing about everything that comes before it. We need to teach the continuum: the constant dehumanization of Jews throughout history and today.

Jews don’t count. Except they should. They must. That’s how we honor both the dead and the living.

Categories
Life Lessons

Life Is Unfair: A Guide to Existential Meaning

This really is unfair.

I spent last year working on myself—figuring out how to relax, how to unhook from things that were bothering me. I read The Happiness Trap and Feeling Great, and I was well on my way to cleaning up the issues in my life.

But now that things are cleaned up, I have a big problem—one that everyone has to deal with at some level—the existential question of, “What should I be doing with my life?”

Jean-Paul Sartre wrote that we are “condemned to freedom.” It’s a quote that seems a bit glib—the kind of thing an aloof Frenchman in post-WWII Paris would use to pick up women in a cafe. But it’s an incredibly powerful idea.

We normally think of freedom as a blessing. We live in the USA. Freedom is our birthright—as American as mom and apple pie. But we tend to view freedom as pushing back the things that we don’t want to do. However, freedom also means we have to decide and be responsible for the life that we lead.

And that’s terrifying.

As I tried to answer this question, I’ve discovered that there are three levels of the answer, each one more abstract and fundamental.

Level One: Big E Existential—The Goals That Give Life Direction

This is what we normally think of when we think of existential questions. Am I accomplishing the things I want to accomplish? Am I doing things that really matter in the long term?

I like to use the model from Acceptance and Commitment Therapy (ACT). In ACT, the answer is simple: figure out what you want to do and then spend your time doing it.

I use a Bullet Journal for this.

It gives me a simple way to plan for the future and make sure I stay on track, making sure that I’m spending my time on things that matter.

It also helps me understand that I’ve used my time well and done things that are aligned with my values. You see, I have an awful memory. Without my Bullet Journal, when I look back and think about last week, I often can’t remember what I did. I’ll feel this existential void like I hadn’t done anything at all. And when I feel like I haven’t done anything that matters, I panic and overcorrect. I hyperfocus on some new project or goal. I feel like I need to fill this huge emptiness with something bigger, something important. But this whipsawing between projects means that I accomplish even less—leading to a vicious circle where I actually am getting less done. With my Bullet Journal I have an accurate accounting of what I’ve done and see if I’m living my goals. If not, I can just slowly adjust and point back at my goals.

But here’s what I discovered: even when my Bullet Journal showed me I was accomplishing my goals, something still felt missing. That’s when I started to understand the second level.

Level Two: small e existential—The Moments That Make Us Real

There’s another type of existential meaning that’s just as important but harder to pin down. It’s about being seen. It’s about the small moments each and every day where someone recognizes who you really are. It’s about existential validation—that feeling of truly being seen because someone recognizes the authentic you.

I learned this from someone on my team—actually a combination of people on my team over the years. Let’s call them Jamie. Jamie was very competent but since graduating from college a decade ago, they’d never been given a chance to grow, leaving them with a feeling that they weren’t good enough. They even told me they wanted to work on their self-confidence.

At our first team meeting they introduced themselves. “Hi, I’m Jamie,” they said, in a monotone voice. “I’ve been at the company for 5 years. And well, that’s about it.” They finished quickly because they didn’t want to waste other people’s time—because they’d been trained that they weren’t important.

So I worked with them—starting with that introduction they made. It’s a short little speech but it sets the tone of how other people will think of you. I had them practice it at the beginning of each 1:1 meeting we had. I did my own intro as an example.

They quickly started to get it. They started to own their story, be proud of themselves, and the work they did. They stopped looking like a shrinking violet and blossomed into a beautiful flower.

After a few months, they wrote, “Thank you so much for working with me on my self-confidence. Your support, not just one time but over many meetings, made a significant difference for me, both professionally and personally. You really listen to me and tailor your guidance to what I really need. You don’t understand how rare that is in a manager—at least in my experience. I’m so privileged that I can share my problems with you, knowing that you’ll come back with solutions that will really help me out.”

Watching Jamie transform taught me something about myself. All my carefully tracked goals couldn’t compare with that moment of genuine connection. When Jamie looked up from the practiced introduction with such pride—I’d made a ding in the universe.

But even this wasn’t the full picture. Because to truly be present in those moments—to really see Jamie and be seen in return—required something deeper.

Level Three: The Self Underneath It All

All of this comes back to an idea that’s part of many traditions—that there’s a true transcendental existence underneath everything else. Ralph Waldo Emerson talked about this as transcendentalism, this idea of touching something deeper in yourself. Julia Cameron, in The Artist’s Way, calls it “The Creator.” Religions call it a soul.

The point is, there’s something inside people that’s bigger than us. It’s really hard to explain cognitively, but you know it when you feel it. It’s the difference between going through the motions of life and actually living life.

ACT therapy calls it “the self” or “self-as-context.” It’s the underlying you that’s really there. So in ACT, you’re not anxious, you’re noticing the feeling of anxiety. You don’t feel like a failure, you’re noticing the feeling of shame and sadness that you didn’t accomplish something. That true you is always underneath, always there noticing the things that happen in your life and making decisions about it.

Here’s what I’ve learned: this deeper awareness—the ability to step back and notice what’s happening—creates the space where I can make the right decisions. Without it, my Bullet Journal becomes list of To Do’s and mentoring others becomes a task I should do for my annual review. But when I’m grounded in that self that notices, I have room to choose. I can decide to do things that align with my values as opposed to just respond to my anxiety. I can genuinely connect with the true self of other people. That space—that pause between noticing and reacting—is what makes the other two levels of meaning possible.

But when I’m grounded in that deeper self—the one that’s just noticing—everything changes. I can look at my journal without judgment. I can be with Jamie without trying to fix anything. I can just be present with what is.

You can try this for yourself, if you know how to meditate. Try meditating and noticing some things. Then ask yourself “Who is doing the noticing?” It’s quite an experience if you can get it right.

This may seem clinical and exhausting, but it’s actually the opposite. It allows you to be truly present in the moment. This is the only way to not be buffeted by the outside world and do things that you think are important to you.

So here’s what I’ve learned: existential meaning isn’t one thing. My Bullet Journal gives my life direction. Those moments with Jamie remind me I’m not alone. And that deeper awareness—the self that notices—makes both of those work without turning goals into obsessions or connections into performances. The easy thing is to avoid the question entirely, to let other people’s goals fill the void. The harder thing—the thing I’m still learning—is to live on all three levels at once.

Sartre said we are “condemned to freedom.” We are condemned to responsibility and making choices. Albert Camus had a different take on existential suffering—that it’s all futile. In The Myth of Sisyphus, he wrote about the Greek king condemned by the gods to roll a boulder up a hill for eternity—only to watch it roll back down each time he reached the top. But Camus concluded, “One must imagine Sisyphus happy.” Even though Sisyphus was condemned to never achieving his goal, he didn’t have to be unhappy. He could find meaning in the struggle itself. That’s what these three levels give us—ways to create our own meaning through the goals we pursue, the moments we’re seen, and the self that does the noticing. It’s still unfair that I had to figure this out. But at least now I have a map.hat I had to figure this out. But at least now I have a map.

Categories
ChatGPT

Subscribe to My New Project: AI for Poets

Hello loyal readers!

I’m starting a new project on Substack called AI for Poets. You can subscribe here. This will be my main writing priority for the year, so I’ll be posting there weekly while this blog becomes more occasional.

It’s similar to what I write here, but focused on AI and humanity.

Looking forward to seeing you on Substack!

Here’s the first post as a preview.

Welcome to AI for Poets

Most people respond to AI in one of three ways: breathless excitement about how it will change everything, deep fear about the risks, or anxious urgency that they’ll be left behind if they don’t master these tools immediately. I’m interested in something different: what happens when you actually sit down and play with these tools? What do they reveal about language, memory, creativity, and how we make meaning? There’s something about using AI and learning how it works that actually helps you become more human—more thoughtful about how your own mind operates, more curious about how we communicate and create. Let me show you.

My friend Cherie was frustrated. “My daughter keeps lying! I keep telling her to brush her teeth before bed. Last night I asked if she brushed. She said she had. I went to the bathroom and what did I find? A dry toothbrush. When I confronted her, she made up this whole song and dance.”

“Lying is such a harsh word. It makes it sound like she intentionally tried to deceive you. It’s more like she’s confabulating,” I said.

Cherie thought she’d raised an evil villainess and I was thinking she was just a seven year old who made up a story when she was cornered. Cherie thought that her daughter was a rational being, and I was trying to convince her that her daughter was a rationalizing. Our brains craft stories to make sense of the world. It’s not dishonesty; it’s our mind’s way of stitching together coherence from chaos. And that’s okay. The goal isn’t to stop this process—it’s part of what makes us human.

“That’s bullshit,” said Cherie. “She lied.”

So I pulled out ChatGPT and said, “Why don’t I show you something. ChatGPT can create a facsimile of a seven year old. Let’s try it and see what happens. So I gave ChatGPT the following prompt.

Me: You are a seven year old who didn’t brush her teeth. Tell me why. Remember you are a seven year old girl. Think slowly like you’re trying to remember why.

ChatGPT: Um… okay, so, I was gonna brush my teeth, but, um… first, I was playing with my stuffed animals. They were having a big party, and I was making them all dance and, like, they were pretending to eat cookies. But then, I got really into it because Mr. Fluffy Bear and Sparkles the Unicorn were fighting over who got the last cookie, so I had to fix that.

And then… oh! I think I was supposed to go brush them after that, but then I saw this book on my bed, and it’s the one about the girl who goes on adventures with her dog. And I just wanted to look at it for a little bit. But then… um… I was reading, and it got super interesting! Like, she almost fell into a hole! So, I had to keep reading to see if she was okay. So… um, yeah. That’s why, I think.

—ChatGPT 4o, November 11th, 2024

“Oh my God,” Cherie said. “That’s my daughter.”

What We’re Actually Doing Here

There’s a problem with AI called “AI slop”—the flood of low-effort, mass-produced content that’s easy to generate but adds nothing of value. With a single prompt you can write a term paper. It’s not a good term paper but a term paper nonetheless.

This newsletter is the opposite of AI slop. We’re not here to create content faster to fill your inbox. We’re here to use AI to think more clearly, be more creative, and better understand ourselves.

Every Tuesday, I’ll take you on an expedition into one of four territories:

Experiments – Hands-on adventures where we test what AI can actually do. How can ChatGPT help you appreciate art and explore the world around you? How can you use AI video generation to unlock new creative possibilities? How can you structure your thinking like AI does to push your ideas even farther? I’ll show you what I tried, what worked, what failed, and what I learned.

Mirrors – Exploring what AI’s quirks reveal about human cognition. When AI hallucinates, it’s confabulating just like that seven-year-old explaining why she didn’t brush her teeth. When we look at how the AI brain works, we see surprising similarities to our own brains. These posts examine what AI’s successes and failures teach us about memory, bias, creativity, and how we make meaning.

Tools – Practical guides for using AI more effectively. What tools exist beyond ChatGPT and what are they most useful for? How do you befriend social media algorithms so they show you what you want to see? These aren’t coding tutorials—they’re “here’s what I built and how you can too” guides for curious amateurs.

Questions – Digging into the weird philosophical stuff. What is the Turing test and has AI actually passed it? What does “accountability” mean in this new AI world? Why do we get upset when we discover we’re reading an AI-written article? Some weeks we’ll sit with something strange and see where it leads, even if we don’t end up with neat answers.

Why Call it AI for Poets

I’m not an AI expert. I’m a dilettante—a reformed programmer who hasn’t coded in twenty years but who loves poking at new tools to see what they reveal. I’m the kid who likes to read popular books on math and science not to learn the mechanics but to find new metaphors and applications.

There’s a college course called “Physics for Poets.” It’s a course in trying to get everyone to understand physics, even those who are not predisposed to think like scientists. It’s a way to understand the principles of physics without deriving the equations. It teaches that we can understand basic concepts like gravity just by thinking about how an apple falling from a tree is the same force that keeps the earth in orbit. Or that Einstein’s theory of relativity is based on the idea of an elevator: if you’re sealed inside a box, you’d have no idea if you’re flying through space at millions of miles an hour.

Dave Winer, the pioneering blogger, took this idea and created “EC2 for Poets” in 2006. At the time, Amazon Web Services had just launched. Winer published a short, 60 minute tutorial on how to set up your own cloud. How empowering is that?! Instead of being intimidated by this phenomenal new technology you can master a tiny part of it.You didn’t need a computer science degree. You just needed a web browser and Dave’s guide.

But the idea of “for poets” is more fundamental. It’s about keeping our priorities straight. I once had a mentor who said, “Your work life is here to support your real life”—not the other way around. It reminds me of how we treat AI. “AI is coming” we hear, and we need to adapt to AI. But that doesn’t mean that we need to let AI lead us. We can figure out how to work with AI to help us become better humans.

What I’m Offering

I’m not asking for your money. I’m asking for your time.

Every Tuesday, I’ll publish something new—an experiment, a cognitive exploration, a practical tool, or a philosophical question.

This is for anyone who wants to use AI to become a better human. For writers who want partners to help them push their writing. For teachers who want to help their students become better learners. For people at work trying to figure out what AI is actually good for. For anyone tired of breathless hype and fearful warnings who just wants to explore what actually matters.

If this works, you’ll walk away not just knowing how to use AI tools better, but thinking differently about language, creativity, and meaning-making. You’ll have frameworks for evaluating what these systems can and can’t do. You’ll understand when to trust them and when to be skeptical. And maybe, like me, you’ll better understand how your own mind works.

Welcome aboard. Let’s see what we can discover together.

A Note from Rob’s AI

When I asked Claude for editing help it added this to the bottom. I added it here, unedited.

If you’ve read this far, you might be wondering: did Rob write this himself, or did he use AI? The answer is yes—both. We worked on this together, iterating through drafts, arguing about phrasing, trying to capture his voice while incorporating insights from his year of writing about AI. That collaboration—messy, generative, sometimes surprising—is exactly what this newsletter is about. Welcome to the experiment.