cities – Scott Loftesness

The apartment was across from Penn Station, which meant that for one stretch of months in the mid-1970s, the architecture of my days was decided by trains I never took. I walked east instead, every morning, toward the United Nations, where a man named Frank Smith ran a personal development course that IBM SRI had decided its young people should sit through. I don’t remember most of what Frank said in that room. I remember one thing he said about the street outside it.

He told us we should start looking up. Literally — on our walks back and forth across midtown, Penn Station to the East Side and back, twice a day, rain or not. Not all the way, usually. Mostly it was a floor or three: the window line just above the awnings, the cornice on a building you’d never once registered had a second story, let alone a sixth. The full climb to the rooflines — gargoyles, setbacks, terra cotta lions — was the occasional reward. Almost no one looks up in New York, he said, not even a little. The city trains you out of it. Too much at eye level demands your attention — the cabs, the steam, the man asking for change, the woman walking too slowly in front of you — so everything above your own eyeline disappears by consensus, not just the tops. Habits can be replaced. Look up enough times, even just a floor or three, and you’ll see a different city than the one everyone else is seeing.

I tried it. Walking up past the Pierpont Morgan stretch, or wherever the route took me, chin lifted some small number of degrees, feeling slightly foolish. Most days that was the whole of it — a window line, a row of air conditioners, a sign painted directly onto brick decades before anyone called that vintage. Every so often the chin would tip back further, and there’d be something up there worth the extra degrees. A gargoyle with its mouth open mid-roar, forty years before air conditioning made gargoyles decorative rather than necessary. But that was the rare find. The habit was the floor or three. Nobody else on the sidewalk was seeing any of it, because nobody else on the sidewalk was looking at all.

The chin came back down on its own a couple of times a week, somewhere around a street corner with a slice joint on it, because New York seems to put one on every corner whether you need it or not. You smelled it before you saw it — that specific combination of tomato, oregano, and hot grease that has no name I’ve ever found. Looking up was Frank’s discipline.

The pizza smell required none. It just reached out and took your head by the chin and turned it level again, toward the window with the steam on the glass and the guy folding a slice in half before he handed it over.

It is a small thing Frank Smith said in a room near the UN fifty years ago, and I have carried it around since the way you carry around a key to a house you no longer own. I don’t know what happened to the course, or to IBM SRI’s faith in such courses, or to Frank himself. I know what happened to the habit. It outlived the year, outlived the apartment across from Penn Station, outlived several cities I’ve lived in since that didn’t have the same vertical drama to reward the looking. I still do it. I did it last week on a walk that had nothing to do with midtown at all, tilting my head back on a street in California to find whatever was up there worth finding, and catching myself mid-gesture, thinking: that’s Frank’s, that one, still running fifty years later on the program he installed.

Most of what we’re taught to notice, we’re taught by people who wanted something from us — a sale, a vote, a grade. Frank wanted nothing, as far as I could tell, except that we see more of the city than we’d been seeing. It’s such a small ambition for a teacher to have. Look up. That’s the whole curriculum. And it’s the only thing from that course, the only thing from that whole strange year of being instructed in personal development by a man whose face I can no longer quite reconstruct, that I still do, unbidden, on every street I’ve walked since.

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.

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