Category: Living

Categories
AI Living

The Threshold

There is a specific feeling. You are trying to understand something — a medical term in a lab report, a clause in a contract, how a particular piece of software actually works under the hood — and you hit the edge of what you know. The territory beyond is unfamiliar and the path is unclear, and something in you decides, quietly and almost without announcement: I don’t know how to figure this out.

And then you move on.

Marc Andreessen, talking to Joe Rogan recently, buried something important inside a longer riff about AI prompting tricks. Most of his list was the kind of thing you’d read in a productivity newsletter — ask it to steelman both sides, pretend it’s a panel of experts. Useful, not revelatory. But one observation was different: pay attention to the exact moment you think “I don’t know how to figure this out.” That’s the moment you should open the AI.

He said it almost offhandedly. I haven’t been able to stop thinking about it.

What he’s really describing isn’t a technique. It’s a behavioral pattern that most of us developed so gradually we don’t recognize it as a choice. The feeling of epistemic overreach — of arriving at the edge of one’s competence — became, over decades, a stopping condition. We learned to treat not-knowing as a wall rather than a door because, most of the time, it functionally was one. The library was closed. The expert was unavailable. The research was paywalled. You moved on.

The habit calcified. Now it persists even when the conditions that produced it no longer apply.

I notice it in myself, and I’m someone who is genuinely curious — who likes knowing how things work, who will follow a thread further than most people bother to. That’s not modesty; it’s relevant context. Because even with that disposition, I still hit the wall. I’ll be reading something and encounter a concept I only vaguely follow — some nuance in immunology, some historical episode I’ve only half absorbed — and I feel the familiar slight contraction, the small withdrawal. I read past it. The curiosity was there. The friction was higher.

Curiosity alone was never enough. What determined whether I pushed through wasn’t how much I wanted to understand — it was whether understanding felt retrievable at all. Most of the time, it didn’t. So I moved on, and the curiosity found something else to chase.

There’s a darker version of this worth sitting with. The people who never developed the quit reflex — who hit not-knowing and felt compelled rather than defeated — are, disproportionately, the ones who built things. The intellectual persistence wasn’t incidental to their contributions; it was probably constitutive of them. Curiosity as stubbornness. The refusal to accept the wall as final.

Elon Musk is the limit case. When he decided he wanted to go to Mars and found the rockets prohibitively expensive, he didn’t defer to the aerospace industry’s consensus about what was possible. He started reading propulsion manuals and cold-calling engineers. The quit signal either never fired or got overridden so fast it made no practical difference. The result was reusable orbital rockets, which the industry had largely decided weren’t worth pursuing. The dig reflex, taken to its extreme, rewrote what was considered feasible.

But the trait is undifferentiated. It doesn’t come with a calibration mechanism. The same refusal to accept expert consensus that produced SpaceX also produces a certain amount of confident wrongness — the Twitter decisions, the Covid takes, the occasional foray into geopolitics with the certainty of someone who has read a lot of Wikipedia. The dig reflex, unregulated, has no obvious stopping condition.

AI doesn’t change that underlying trait. What it changes is the access cost for everyone else.

For most of human history, the friction wasn’t random. It selected for people whose drive was strong enough to overcome it regardless of cost — the right connections, the right institution, the time to burn. Now that friction is lower for everyone, nearly to zero, for an enormous range of questions.

What I’m trying to build is the opposite of the quit reflex. Not the Musk version — boundless, uncalibrated, occasionally catastrophic. Something more modest: the habit of checking before giving up. Noticing the moment of not-knowing and treating it as a question rather than a verdict.

It requires noticing the moment. Which is harder than it sounds, because the reflex is fast and the moment is brief.

The contraction happens. You’ve already moved on. Somewhere behind you, the question is still there.

Categories
Haiku Living Reading

The Presence We Keep Deferring

I have so many unread articles saved to Instapaper that I’ve stopped checking the count. Each one felt, in the moment of saving it, like something I needed. A long piece on urban planning, a profile of someone interesting, a reported essay I fully intended to sit with.

The app is beautifully designed for exactly this — the frictionless capture, the clean reading interface waiting patiently on the other side.

What it can’t do is manufacture the attention I didn’t have when I saved it and still don’t have now. The articles aren’t the problem. The premise is: that presence is something you can bank.

There’s a haiku I keep returning to, from Natalie Goldberg’s Three Simple Lines. It’s by a poet named Fumiko Harada:

Morning chill
I savor this moment —
one meeting one lifetime

Eleven words. No verb in the third line, which makes it feel less like a thought and more like a verdict.

The Japanese concept underneath it is ichi-go ichi-e — loosely, “one time, one meeting.” It’s a Zen idea with origins in the tea ceremony, the understanding that each gathering is singular and therefore irreversible. You cannot archive it. You cannot search for it later. When it ends, it doesn’t go anywhere you can retrieve.

This is what the Instapaper queue is, at scale: an archive of moments I decided to experience later. The article about urban planning was written by someone who spent months reporting it, on a day when some editor thought it was ready, and landed in my feed on a morning when something about the headline caught me. That constellation doesn’t reassemble. Later is a different article.

The tools I use every day are getting astonishing. There are systems that can summarize, translate, recall, explain, anticipate. I use them. I find them genuinely useful.

But there’s a habit of mind they reward — a kind of perpetual deferral of full attention — that I haven’t fully reckoned with. The promise, always, is that you can engage more completely later, once the summary is ready, once the transcript exists, once the notes have been taken. Presence becomes a productivity tax you pay while waiting for a deliverable.

Harada’s haiku doesn’t moralize. The speaker isn’t lecturing herself into awareness. She’s just cold, and awake, and choosing to notice. I savor this moment. The word “savor” does a lot of work. It implies effort. You savor things that could be missed.

The pivot in the third line is what stays with me. One meeting one lifetime. Not “this meeting will last a lifetime” — that would be sentiment. It’s more like a mathematical statement: the cardinality of this encounter is one. There is exactly one of them. This morning, this particular chill, whatever conversation or solitude is happening inside it — that set has one element. By tomorrow it has zero. No amount of documentation changes that arithmetic.

I’m working on believing that.

Categories
Living Retirement Sports Writing

The Architecture of a Wound

I have read a lot of Wright Thompson pieces over the years. Enough to notice that I finish them feeling slightly implicated — like I have been shown something true about a person I thought I understood, and the showing has cost me something comfortable. That’s not a common feeling after reading sportswriting. Thompson’s a different kind of sports writer.

His profile of Steve Kerr, published this week in ESPN, is a case study in how he does it.

Go read it now. Before you continue here. Go read it!

The opening line: “Steve Kerr walked into the lobby of the Beverly Wilshire with a secret.”

Thompson doesn’t start with biography or context or the Warriors’ season. He starts with dramatic irony — we are placed inside a moment where the subject knows something we don’t, where the gap between public persona and private reality is already established before we’ve gotten through the first sentence. We know, even before we know what the secret is, that the real story will be about what lives underneath the official one.

The secret is retirement. Kerr had made up his mind — 95% certainty — that this would be his last season. He checked in at the Beverly Wilshire, gave his room number, 516, as “Johnny Bench Joe Montana,” and then leaned across the breakfast table and almost mouthed the words: “I think it’s over.”

That room number detail is worth pausing on. It isn’t decoration. A man who has spent 40 years inside professional basketball has encoded legends into the passwords of his daily life — Bench’s number, Montana’s number, woven together as a mnemonic for a hotel room he’ll forget in three days. Thompson drops it and moves on without comment. He never explains it. He doesn’t have to. The detail does its work the way a good poem does: you carry it with you, and it means more the longer you hold it.

This is the loaded object, and Thompson deploys it everywhere. Late in the piece, the coaches bond over the same memory trick on the road — Thompson tells Kerr he’s in room 2225, “Emmitt Smith Rocket Ismail.” The repetition isn’t accidental. It’s Thompson showing us what the 82-game season actually is: a long chain of hotel rooms and encoded legends, a man building temporary homes out of other people’s greatness.

Thompson earns the loaded objects by earning the access. He spent the entire season alongside Kerr — embedded, unhurried, a still presence at the edge of the frame. The piece has the texture of someone who was there for the small moments precisely because he wasn’t hunting the big ones. He’s in the coaches’ locker room after losses, cracking Peronis on the team bus through the quiet midnight of Atlanta, at Pizzeria Bianco in Phoenix, at the Golden Gate Deli while Kerr eats his usual Honey Baked sandwich and texts “Conflicted” and then adds: “What’s Lulu think?” “She sees both sides.”

That kind of detail — the dog with two minds about retirement — is available only to a reporter who has spent enough time with a subject that the subject has stopped performing. Thompson collects these moments. They are the material.

But access is scaffolding. The building is what Thompson does with it.

Midway through the piece, he lands the paragraph that reorients everything that came before it. On January 18, 1984, a gunman shot Malcolm Kerr — Steve’s father, president of the American University of Beirut — in the head. A family friend reached Steve in his dorm room at 3 a.m. Steve asked if his father was okay. There was a long pause. “Your father was a great man,” the friend finally said.

Steve ran downstairs and pounded on his teammates’ doors. Then he went and sat on the curb. “On Speedway Boulevard,” he says, still remembering the cold concrete and the empty street. Thompson gives us that street name. He tells us Steve started walking, and that he hasn’t slowed down since.

Suddenly the retirement question isn’t about basketball at all.

The sport is Thompson’s vehicle. His real subject is always the wound underneath — what drives a person to keep competing, keep building teams, keep moving, and what it means when the movement finally starts to slow. The question running beneath the entire Kerr piece isn’t “Will he stay or go?” It’s the question Malcolm’s assassination put into his son at 18, still unanswered 42 years later: what do you do when the thing that protected you from the worst moment of your life stops being available?

Thompson makes this explicit in one passage near the end. Kerr describes his fear about retirement: the coaching job, he says, doesn’t just feed his soul — it helps him manage his chronic daily pain. The pain, we’ve learned by then, is rooted in unresolved trauma. Kerr has spent a year journaling every morning about his father’s death and then deleting what he wrote, following a therapy program based on the idea that emotional wounds express themselves as physical ones. The back pain that plagued him for 12 years — the migraines, the spinal leak, the decade of searching for relief from Mayo to Duke to England for stem-cell therapy — began the same year he took the Warriors job. Writing opens the lines of communication. Winning keeps them open. Retirement threatens to seal them again.

Thompson doesn’t editorialize. He just lays this all out, piece by piece, until the architecture becomes visible.

There’s a moment in Minneapolis, late in the piece, that sticks with me.

The NBA has postponed a game after a nurse named Alex Pretti has been killed by federal agents. Kerr gathers the team in a hotel ballroom. Later, working through what to say publicly, he does something Thompson says he’s never heard him do before — he invokes his father.

“My father was killed by extremists,” Kerr says, rehearsing lines. “I know how that story ends.”

Thompson can hear his voice catch between sentences. “I’m crying right now,” Kerr says.

At the press conference, Kerr doesn’t mention his father. He talks about the families who will never get their loved ones back. He didn’t have to say more. And Thompson, who was there for all of it — the hotel ballroom, the phone call, the media room — doesn’t have to explain the connection either. He’s done the work of showing us who Malcolm Kerr was, what his assassination meant, how Steve has carried it. The press conference lands with the full weight of everything we’ve already been given.

This is Thompson at his best: information as infrastructure, detail as detonator.

The piece ends not with a contract signing or a press conference. It ends with a granddaughter.

On the same day Kerr commits to returning — the decision made, the call to Steph placed, the band getting back together — his son’s younger daughter, Charlotte, takes her first steps. Kerr watches her toddle around the room. He thinks about his son as a toddler. He looks at the photograph on the wall of Nick and his older daughter grinning in front of the Golden Gate Bridge. “It all felt intertwined,” Thompson writes. “Blood family, basketball family, family. A cocoon, like his old Arizona manager said.”

That word — cocoon — has appeared once before. It’s what the Arizona manager called the arena the night Steve played two days after his father was killed. The crowd forming a protective warmth around a boy who had just lost everything. The team as shelter.

42 years later, it’s still what Steve Kerr is building and protecting. Thompson knew to plant the word the first time so it could bloom at the end.

That’s the technique. That’s what I mean when I say reading him costs something. In a wonderful way. He shows you that the things people build — teams, careers, dynasties — are sometimes just very elaborate answers to questions they were asked at 18 on a cold curb on Speedway Boulevard. And then he leaves you with a baby taking her first steps, and you feel the whole weight of it all at once.

Categories
Family Fathers Living Sports

The Flashlights He Left Behind

There’s a Wright Thompson piece from 2007 that I keep returning to. It was filed during the Masters, and it’s technically about golf the way the ocean is technically about water.

The setup is simple: Thompson is at Augusta National for work, credentialed sportswriter in the press tent, watching the ceremonial first shots and the azaleas and all of it. His father had dreamed of attending just once. His father is dead. The piece is what happens when Thompson walks the course trying to find him.

I don’t know how to write about it without sounding like I’m describing a dream to someone who wasn’t there. So let me start with the craft.

Thompson opens with chipped beef on toast. He’s on the clubhouse veranda, waiting for Arnold Palmer, and a stranger asks what he ordered. “It was my dad’s favorite meal,” Thompson explains. A silence falls. “Did you ever bring him here?” the stranger asks. “No,” Thompson says, turning away.

That’s the whole wound, opened in three lines of dialogue. No commentary. Just the weight of the unanswered invitation — the trip that never happened — sitting there in a plate of chipped beef. The best sportswriters understand that the specific detail does what abstraction never can. Thompson doesn’t tell you he carries grief. He shows you where it lives.

Then comes the structural move that makes the piece something more than a personal essay. Thompson builds a rhythm — three times, he lands the phrase that is Augusta — each time widening the frame. Nicklaus on 18, glancing at his son, repeating his own father’s last words. Tiger winning in 1997, finding Earl in the gallery, a son’s head on a father’s shoulder. And then, quietly, devastating: This, too, is Augusta: me, needing a daddy more than ever.

By the time the narrator’s grief enters the frame, the reader has already been prepared to receive it. The repetition is a kind of structural kindness. Thompson is telling you: pay attention, something is being built here. When it arrives, it doesn’t feel sudden. It feels inevitable.

The piece has a spine you don’t notice until you’ve read it twice. Thompson asks the same question at two different moments: Daddy, are you out there?

The first time, he’s standing in the rain, alone, by a sapling planted exactly one year after his father’s death. He’d been standing guard over the tree in a downpour, soaked, because he’d been unable to protect his father in life. No answer comes. Just the shattering windows of water falling from the sky.

The second time, he’s in the bleachers at Amen Corner. He whispers it. And from somewhere across the course, a roar rises from the gallery, moving through the pines, fading back to silence.

Thompson is careful here. He writes: Understand that I don’t believe in stuff like this and am certain it is a coincidence. That hedge is the whole story. The man who doesn’t believe in signs is exactly the man who most needs to find one. The moment works precisely because he doesn’t oversell it. He puts it down and lets it be what it is — or what the reader needs it to be.

The passage I keep coming back to is near the end, not at the emotional peaks. Thompson has just watched Jim Gray, the television reporter, carefully lift the rope so his white-haired father can slip beneath it. A small thing. A son holding a rope. And Thompson realizes he’s watching himself in reverse — that the transition he’s been grieving his way through is also a transition toward something.

The piece ends not with closure but with continuation. He buys a tiny green Masters onesie. A small knit golf shirt for a toddler. And the last line the sales clerk offers — meant as a coo over the cute little clothes — lands as the verdict Thompson has been seeking all week: Oh, good daddy.

It’s the right ending because it doesn’t answer the grief. The hole in your chest after losing your daddy never gets filled, Thompson writes, and he means it. What the ending does instead is redirect the inheritance. He’s received everything he needed. He just needs to pass it on.

That’s what the best longform sportswriting can do when it’s working at full power. The Masters is the container. Inside it: a meditation on what fathers give us that we don’t fully inventory until they’re gone, and what we owe the children we haven’t had yet.

Thompson filed this piece for a newspaper. He was 30 years old. That this exists at all feels like its own small miracle — a man sitting down in grief and producing something that will outlast the tournament, and probably him.

Go read it. The link is here. Then come back and sit with it for a while.

Categories
Books Curiosity Living

Working the Seams

This book highlight popped up in my morning Readwise feed recently:

“Fishermen work seams—seams between slow water and fast, between deep water and shallow, between sunlight and shadow. The eddies around rocks, the bubble lines along banks. That’s where the fish are.”

Neil King wrote it in American Ramble, his account of walking from Washington to New York. He was watching fishermen, not fishing himself, which maybe explains why it reads less like instruction and more like revelation. When you’re the observer, you have room to notice what the practitioner is too busy doing to say.

The word seams is doing something I can’t stop thinking about. A seam is a joining. It’s the place where two different things meet and, in meeting, create a third thing: the edge itself. Not slow water, not fast water, but the turbulent conversation between them. The fish aren’t in the slow water. They aren’t in the fast water. They’re in the argument.

I think most of the interesting things in life happen at seams.

The best conversations aren’t the ones where everyone agrees. They’re the ones where two people with genuinely different orientations are standing at the same edge, looking at the same water. The friction between the views creates something neither would reach alone.

The best writing isn’t the settled opinion, the fully-arrived-at conclusion. It’s the essay in the old sense — the attempt — where you can feel the writer at the seam of what they know and what they’re reaching toward. The bubble line between understanding and confusion. That’s where the reader is, too, if they’re lucky.

I notice this on my own blog sometimes. The posts that feel most alive to me aren’t the ones where I knew what I wanted to say before I started. They’re the ones where I began at a seam — between something I’d always believed and something that recently unsettled it — and wrote my way along the edge, not knowing which bank I’d end up on.

There’s a version of this that applies to attention itself.

I dwell on how I pay attention — when I’m reading, when I’m walking, when I’m in conversation. And I’ve noticed that my attention goes flat in the middle of things. Flat terrain. Constant depth. Unchanging light. I have to work to stay present when nothing is in transition.

But put me at a seam — a moment where the mood in a room is shifting, where a piece of music is about to resolve or refuse to resolve, where someone is on the verge of saying something they’ve been circling for an hour — and I’m completely there. Attention is predatory, maybe. It goes where the tension is.

Which is what the fish are doing, of course. The seam isn’t just a metaphor for where interesting things happen. It’s why interesting things happen there. The fast water sweeps food along; the slow water lets you hold your position; the seam between them is where you can eat without being eaten. The fish are solving a real problem. They’re just also, accidentally, living beautifully.

I wonder sometimes if this is what makes a good editor, or a good friend who reads your drafts. They find the seams — the places where you’ve unconsciously papered over a tension, smoothed the fast water into the slow, given the reader no place to be a fish. “Something’s off here,” they say, and what they mean is: you resolved this too quickly. Stay in the argument longer.

The eddies around rocks, the bubble lines along banks.

I want to be a better noticer of those. Not to resolve them. Just to work them.

Categories
Business Living Retirement Trading

The Whetstone and the Hammock

We spend the first half of our lives trying to build a fortress of comfort, operating under the assumption that the ultimate reward for a lifetime of labor is the sudden, permanent cessation of it. We dream of the hammock. We dream of the empty calendar. But an empty calendar is really just a blank canvas with no paint.

Patrick O’Shaughnessy recently sat down with Paul Tudor Jones, and their conversation inevitably drifted toward the later chapters of life. Jones shared a story about fulfilling a promise to his wife to move to Palm Beach after their youngest child went to college. Upon arriving, she sent him to a local general practitioner—an 83-year-old doctor still seeing patients. Jones asked the man for the secret to longevity in a town (Palm Beach) he bluntly described as the “land of the walking dead.” The doctor’s response was a swift hammer blow:

“It’s real simple. You retire, you die.”

It’s a jarring diagnosis, but it cuts right to the bone.

We are biological machines designed for friction. Take away the resistance, and the gears don’t just stop; they rust.

Jones took the lesson to heart, noting that if you don’t use it, you lose it. He works out two hours a day and continues to trade, deliberately keeping his mind pressed against the whetstone of the markets.

I’ve watched this play out in my own circles over the years. I’ve seen brilliant, energetic colleagues hand over their keys, step out of the arena, and within months, seemingly deflate. The sudden absence of daily problems to solve doesn’t bring peace; it brings a creeping atrophy.

I’ve found myself deliberately holding onto certain complex projects and investments not because they are financially necessary, but because they demand my attention. They force me to wake up and solve a puzzle. They provide the necessary gravity to keep my feet on the ground.

But Jones offered a second, perhaps more profound reason for staying in the game. He wants to make “an absolute pot of money” specifically to give it away. He views his daily work not as a grind, but as the pursuit of nobility. He found a way to bridge the gap between the selfish need to keep his own mind sharp and the selfless desire to fuel the causes he cares about. The work becomes an engine for something larger than himself.

The hammock is a trap. The mind requires weight to bear, a horizon to move toward. The goal is not to finally lay down our tools, but to choose precisely what we want to build with them until the very end.

Stay hungry, stay foolish – and stay busy!

Categories
Living Serendipity Travel

The Conditions of the Unexpected

There is a flight I took in 2001 that I have never fully stopped thinking about. Not the flight itself — a forgettable three-hour hop in a middle seat — but the two-hour delay that preceded it. The gate agent’s apologetic crackling over the intercom. The way I surrendered to the terminal, found a bar stool, ordered something I didn’t need. The man next to me was reading a book I recognized. We talked for two hours. He told me about a job. I didn’t take it — but I spent three months considering it, which is its own kind of detour. I came out the other side different in ways I still can’t fully account for.

I have told this story before as a story about luck. I’m not sure that’s what it is.

Alexander Krauss spent years going through the records of science’s major discoveries — Nobel Prize winners, the landmark non-Nobel findings, more than 750 in all — looking for the mechanism behind what everyone had been calling serendipity. The telescope trained on an unexpected patch of sky. Fleming’s contaminated petri dish. The chance observation that shouldn’t have meant anything but did.

What he found upended the romance of the story. The discoveries that seemed most accidental, most shaped by the caprice of an unlucky sneeze or a mislabeled sample, turned out to follow a pattern. Nearly all of them happened shortly after a researcher gained access to a new tool. The accidental observation of cells under an improved microscope. X-rays discovered through a discharge tube nobody had pointed in that direction before. The first planet beyond our solar system, caught by a spectrograph that hadn’t existed a few years earlier. What looked like lightning striking the same improbable spot again and again was actually the same thing each time: a new instrument creating the conditions under which something unexpected could be seen.

Krauss calls this “engineering serendipity.” The phrase stops me every time I read it, because it sounds like a contradiction and turns out to be the most practical sentence in the philosophy of discovery. You can’t engineer the specific surprise. But you can engineer the conditions that make surprise likely. You can build the lens before you know what it will show you.

This distinction — between engineering an unexpected discovery and engineering the conditions for unexpected discovery — is one I’ve been carrying around like a stone in my pocket. Because I think it applies far outside the laboratory. I think it’s one of the central design problems of a life.

The book trend critics are calling “Digital Nostalgia” is, depending on how you read it, either the most sentimental or the most diagnostic thing happening in literary culture right now. The novels topping lists this spring are full of people losing their recordings, waking up in centuries without algorithms, mourning the weight of analog things. Ben Lerner’s new novel begins with a dropped phone in a hotel sink — the recording gone, the moment unrecoverable. Caro Claire Burke’s Yesteryear sends a social-media influencer back to an 1855 that is nothing like the one she curated for her followers: cold, filthy, unfiltered, and somehow more real.

What readers are reaching for in these books is not the past per se. It’s the texture of a life that wasn’t predicted in advance. The feeling of not knowing what came next because nothing had pre-sorted the possibilities. Nostalgia, in its root meaning, is pain at being far from home. What Digital Nostalgia seems to be mourning is something more specific: the disappearance of accident from everyday life.

I notice this in small ways. My phone knows where I’m going before I’ve decided to leave. The algorithm has predicted, with unsettling accuracy, what I will want to read next. The coffee shop I found by walking down an unfamiliar street now gets recommended to me, which is useful and also somehow diminishes the thing I found. The city I live in has become a more efficient version of itself. Less of it surprises me than used to.

This is not entirely bad. But something is lost in the smoothing. And the books people are buying tell you what.

The urbanist argument for cities has always included, at some level, an argument for density as a serendipity engine. You put people in proximity. You make them share transit and sidewalks and bars and parks. Intersections happen. Ideas cross. The great creative explosions of modern history — Florentine painting, Viennese psychoanalysis, the Bell Labs cafeteria — were products less of individual genius than of designed proximity. People who wouldn’t have met each other kept meeting each other.

What’s interesting about Krauss’s argument is that it generalizes this principle to the history of science in a way that makes it quantifiable. It’s not just that cities were generative because they were dense. It’s that they were generative because they were full of new tools — printing presses, coffeehouses, salons — that created new surfaces where minds could collide and refract in new ways. The tool doesn’t make the discovery. It makes the discovery possible, and likely, and reproducible by others.

Which brings me back to the airport bar.

The two-hour delay created an unstructured interval I hadn’t planned for. I didn’t know what to do with it, so I sat somewhere I wouldn’t normally have sat. The man next to me had a book that served as an opening. We were both temporarily outside our routines, which is another way of saying: we were both in a new instrument, looking at something we hadn’t known to look for.

What I’ve been slow to admit is that this kind of moment doesn’t just happen. It happens to people who are outside their routines. It happens in places where unlike people are forced into proximity. It happens when you sit down somewhere without your headphones, without a screen to retreat into, in the condition of being briefly unoptimized. The delay was the tool. The discovery followed.

So here is the tension I keep returning to: you can engineer the conditions for serendipity, but you cannot engineer serendipity itself, and the engineering has to be genuinely open-ended or it stops working. If you design a system that produces specific surprises, you haven’t built a serendipity engine. You’ve built a surprise dispenser, which is a different and lesser thing. Amazon’s “you might also like” feature is not serendipity. It is prediction wearing serendipity’s clothes.

The difference is whether the system preserves its capacity to show you something it didn’t know you needed to see. A new microscope could reveal anything. A recommendation algorithm reveals only a constrained neighborhood of the space of things you’ve already wanted. The former is a lens. The latter is a mirror.

I think this is what the Digital Nostalgia readers are grieving, without quite being able to name it: not the analog past itself, but the unoptimized interval. The moment between knowing what you wanted and finding it, when anything might happen. That space has been shrinking for twenty years, and the algorithm’s promise — to eliminate friction, to anticipate, to smooth — has turned out to be partly a promise to eliminate possibility.

The question I’m sitting with is whether it’s recoverable. Not globally — I’m not interested in the manifesto version of this argument, the call to smash the phones or return to the forest. But personally. Whether I can design my own life to include enough genuine aperture — enough unoptimized intervals, enough new tools, enough places where I am briefly outside my routine and available to be surprised — to keep the surprises coming.

I have some guesses about what this looks like. Reading outside my field. Saying yes to the conversation I don’t have time for. Choosing the longer route. Leaving earlier so the delay doesn’t feel like a crisis.

These are small things. They are also, if Krauss is right, approximately how all the important discoveries get made.

The flight eventually boarded. I didn’t take the job. But I thought about it for three months, which means I thought about my actual life for three months — what I wanted from it, what I was settling for, what I hadn’t been willing to name. The man at the bar didn’t change my path. He changed my angle of view, briefly, enough. I’ve been a little suspicious of smooth trips ever since.

Categories
Books Living Quotations

The Smallness of Being Nowhere

There’s a sentence I keep returning to from Blue Highways, William Least Heat-Moon’s account of driving the back roads of America after his marriage ended and his teaching job disappeared in the same week:

“In a hotel room at the geographical center of North America, a neon sign blinking red through the cold curtains, I lay quietly like a small idea in a vacant mind.”

I’ve read it probably a dozen times now and it still does something to me. The question I can’t shake: why does it work so completely?

The setup is all precision and specificity. “The geographical center of North America” — Heat-Moon is actually in Rugby, North Dakota, a place so particular it exists mostly as a fact. You cannot be more specifically somewhere on a continent and also be more nowhere. That’s the first compression: location as the opposite of orientation.

Then the neon sign. Red through cold curtains. He doesn’t describe the room — the bed, the low ceiling, the highway sound. He gives you the one sensory detail that pulses, that intrudes. Red blinking through fabric. That’s loneliness rendered as light. You don’t need the rest of the room. You already know it.

And then the simile arrives, and it’s the sentence’s whole reason for existing.

Like a small idea in a vacant mind.

What’s strange is that it shouldn’t work. It’s abstract — ideas, minds — in a sentence that’s been building toward the physical and concrete. But Heat-Moon has earned the turn. He’s given us geography, then sensation, and now he cashes both in for something interior. The simile tells you exactly how the previous details felt from the inside: not tragic, not dramatic, not even particularly sad. Just small. A flicker of thought in an empty space.

The word “quietly” is doing more than it announces. He doesn’t lie there awake or restless or afraid, all the words that would have been available and true and insufficient. He lies quietly, which is a posture, not an emotion. It places him in the scene without claiming too much about what the scene means.

This is what I find myself most drawn to: the sentence doesn’t reach for profundity. It doesn’t tell you this moment is significant, doesn’t linger on the loss that brought him there. It just describes, precisely, what it’s like to be a self that has temporarily lost its weight — to exist at the center of something vast while feeling like an afterthought in your own head.

There’s another line from the same book that works entirely differently, and I keep it nearby as a kind of corrective:

“Life doesn’t happen along interstates. It’s against the law.”

The first sentence is a philosophy. The second sentence is a joke about highway regulations that somehow confirms the philosophy. The gap between those two moves — the microsecond where you process that he means both things — is where the humor lives.

What’s funny is also true: the interstate is literally designed to prevent you from stopping, from turning off, from being anywhere specific. You are processed through the landscape like freight. Heat-Moon understood that the road you take isn’t a neutral choice. The blue highways of the title — the old two-lane routes, drawn in blue on gas station maps — were the ones where you might actually arrive somewhere, talk to someone, become something other than your destination.

The joke earns its keep because it doesn’t explain itself. He trusts you to feel the absurdity and then sit with the fact that absurdity is sometimes just accuracy.

What strikes me, holding both sentences together, is how much range lives in a single book. The hotel room passage asks you to feel the weight of smallness. The interstate line asks you to laugh at the systems we build to keep life at a safe distance. Both are true. Both are, in their different registers, about the same thing: what you miss when you move through the world without stopping.

That’s what the geographical center does. At the exact middle of a continent, you are as far from every edge as you can be. You are equidistant from significance. The neon blinks anyway. And you are there, small, in the dark — on a blue highway, not an interstate. Which means, at least according to Heat-Moon, that something might still happen.

I don’t know why I find this more moving than sentences that try harder. Maybe because precision, applied to the right details, is its own kind of tenderness.

Or maybe it’s just that I’ve been that small idea in a vacant mind, and it’s a relief to find it named.

Categories
Living Serendipity

Why Comfort Zones Block Serendipity and Growth

Barista preparing coffee with customers sitting and chatting in a cozy café
Customers enjoy coffee and pastries in a warm, inviting café

Serendipity used to be the default setting of my days, but recently I find myself having a quiet, losing negotiation with the front doorknob every time I try to step outside. There is a specific, invisible weight to the handle on a quiet evening—a subtle, undeniable gravitational pull that recommends I simply stay inside. My favorite reading chair feels less like comfort these days and more like an anchor.

I have been writing in this space since 2001. If you look back through the archives of my life—both the digital ones and the memories filed away in my head—you will find a younger version of myself who frequently and willingly threw himself into the unknown. Back then, I assumed serendipity would always just be there, waiting for me to stumble into it on a diverted commute or during a late, unplanned dinner.

Lately, I’ve noticed a subtle shift. As I’ve gotten older, my comfort zone has hardened from a permeable boundary into a brick wall. The things that once sparked a quiet thrill of spontaneity—a sudden change of travel plans, an unfamiliar route home, saying yes to an event where I know absolutely no one—now often trigger a low-grade exhaustion before they even begin. I find myself pre-calculating the energy cost of every deviation from the routine. I weigh the known comfort of my home against the unpredictable variables of the outside world, and the home usually wins.

But I have been sitting with a growing realization lately: when we meticulously optimize our lives for comfort, we inadvertently foreclose on serendipity.

Serendipity requires a loose grip. It demands a willingness to be occasionally inconvenienced. You cannot schedule a chance encounter, and you cannot algorithmically generate a moment of sudden, blinding clarity. Those things only happen in the messy, unmapped spaces between our planned destinations. They live in the friction of the unexpected.

I often think about the writers and thinkers who deliver sentences with such compression and weight. Their most profound insights didn’t arrive because they stayed perfectly insulated from the world. They arrived because they allowed themselves to be interrupted by it.

I am trying to learn how to open the door again. It doesn’t mean manufacturing chaos or pretending I have the boundless, restless energy of my thirties. Acknowledging my own changing capacity (especially physically) is necessary, but using it as an excuse to stop exploring is a mistake.

Overcoming this gravity means making a conscious, deliberate choice to leave the itinerary blank for an afternoon. It means taking the long way home, even when the usual route is faster. It means accepting that the discomfort of stepping outside the routine is the unlock to open a new experience.

The architecture of a well-lived life isn’t built out of safety. The most interesting rooms are the ones we never intended to enter but just happened into.

Categories
Living

The Unpadded Saddle

The clatter of the wooden track arrives before the speed does. It starts as a gentle rumble beneath the floorboards, deceptive in its innocence. Then the trumpet fanfare blares, the recorded call of “And they’re off!” echoes across the platform, and suddenly you are caught in a centrifugal force violently pulling you toward the edge.

We are so accustomed to the padded corners of our routines that the Derby Racer at Rye Playland feels almost transgressive. Built in 1928, it is one of the world’s last surviving racing carousels. But the word “carousel” implies a gentle, music-box rotation—a docile circle meant for toddlers and waving parents. The Derby Racer, by contrast, spins at nearly twenty-five miles per hour. You sit astride a hand-carved wooden horse, one of fifty-six crafted by Marcus Illions, that leaps and pitches forward and backward with a startlingly realistic gait.

There are no lap bars. There are no padded shoulder restraints locking you into a prescribed posture of safety. There is no automated sensor to ensure you are seated correctly. There is only a metal hoop, your own grip, and gravity.

I remember taking a ride on the Derby Racer years ago. I climbed into the saddle, wedged my right foot onto the top peg and my left onto the bottom, exactly as the operator instructed. Lean in hard or you’ll fall off, the safety spiel went. As the speed built and the outward pull tried to peel me off the horse, my arms began to burn. My thighs locked against the painted wood. The wind whipped my face, and the track roared beneath us. It was exhilarating, yes, but it was also genuinely demanding.

When the ride finally slowed and I dismounted, my legs were wobbly. Beneath the lingering adrenaline was a profound, quiet relief: I had survived.

In 1928, the world was a less insulated place. The people who first rode those Marcus Illions horses understood that machinery required respect. They didn’t expect the ride to take care of them; they understood the unwritten contract of the saddle. Returning to it now feels like stepping through a portal into an era that trusted individuals to hold their own weight.

We spend so much of our time engineering physical risk out of our days. We build software to prevent errors, algorithms to smooth out our choices, and bumpers to keep us firmly in our designated lanes. We have traded the raw, unrefined thrill of hanging on for the predictable comfort of being strapped in. We assume that a frictionless experience is always a better experience.

But there is something deeply necessary about a machine that demands your active participation just to stay aboard. The Derby Racer doesn’t care if you are distracted; it requires your attention in the present tense. It forces you out of the abstract anxieties of your mind and entirely into the burning muscles of your arms and legs. It reminds you that the physical world still has teeth, and that staying upright requires deliberate, conscious effort.

The padding of the modern world keeps us comfortable, but the raw grip of a 1928 wooden track reminds us we are alive.