Tag: writing

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Writing

Wait, What? The Art of the Irresistible Lead

A few weeks ago I sat with a fresh draft of one of my daily reports, the cursor blinking on a perfectly serviceable first sentence. It told the reader exactly what the piece was about. It was clear. It was polite. And it was, frankly, a little boring.

I deleted it and tried again. Then again. On the fifth try, something shifted. The sentence wasn’t flashy, but it carried a quiet spark of surprise—an unexpected detail that made even me lean in. In that moment I felt the familiar thrill of a good lead doing its quiet work: not demanding attention, but inviting it.

Susan Orlean has long been one of my quiet heroes in this regard. She crafts first sentences that land like gentle provocations—declarative, sometimes absurd, always authoritative in their own small way. They dare you not to keep reading, even when the subject seems, at first glance, ordinary.

For years now I’ve paid close attention to these opening moves—not just in Orlean’s work, but across the writers who consistently pull me in and refuse to let go. In a world of endless distractions and shorter attention spans, the lead is no longer optional; it is an act of hospitality. It says, gently but firmly: Come sit with this for a while. There’s something worth your time here.

This post is my reflection on that craft—why it matters, what the masters do so well, and how those of us who write (whether for blogs, reports, letters, or larger ambitions) might get better at it. Along the way I’ll share specific examples that still make me pause and smile, plus some practical ways I’ve tried to strengthen my own first sentences. Because if curiosity and receptivity are part of my compass, then learning to write better leads feels like one small, ongoing way to live into that.

Why Leads Matter More Than Ever

Attention is the scarcest resource we have. A strong lead doesn’t just inform—it seduces, surprises, or jolts the reader into “Wait, what?” mode. It earns those first crucial moments in a distracted world.

When I struggle with a draft, it’s often because the opening is doing too much summarizing and not enough inviting. A great lead respects the reader’s time while promising payoff. It’s generous. And in my own writing, whether a morning report or a more personal essay, refining the lead has often clarified the entire piece.

Masters of the Lead

Over time I’ve noticed how the same principles appear across very different forms. Feature writers like Susan Orlean seduce us into caring about subjects we didn’t know existed. Obituary writers work under tighter constraints but with profound stakes—distilling a life into something that honors the dead while engaging the living.

Orlean often opens with vivid, affectionate character portraits or surprising details that feel like delightful invitations. One classic: “In Bulgaria, some tennis balls are like dumplings.” It’s playful, specific, and instantly makes you wonder about the world these athletes inhabit. Another strength is the rapid, layered sketch: “John Laroche is a tall guy, skinny as a stick, pale-eyed, slouch-shouldered, and sharply handsome, in spite of the fact that he is missing all his front teeth.” The list is cinematic; the twist humanizes. Orlean writes the way a reader experiences the story, starting at the beginning and pulling you along with warm observation.

Obituary writers like Alden Whitman show the form’s power under pressure. Whitman conducted thoughtful advance interviews, framing them as biographical updates rather than morbid exercises. He asked reflective questions about identity, turning points, and what mattered most—gathering the intimate details that made his leads gracefully revealing. His portraits treated lives as coherent stories, full of flavor and humanity. Modern masters like Margalit Fox continue this with witty, precise openings that capture essence in one surprising stroke. British obituary traditions add elegant wit and anecdote, often using a single eccentricity to humanize even formidable figures.

The contrast is illuminating. Orlean’s warmth draws you in with delight and empathy. Joan Didion might open the same subject with cool cultural dissection, noting contradictions and performance. Wright Thompson would make it mythic and sensory. Jimmy Breslin would give it street-smart heart and working-man respect.

I sometimes test this by imagining how each would open a scene I actually remember: Moe’s Books on Telegraph Avenue in 1969. I was young, new to Berkeley, and the place felt like a sanctuary. The cigar smoke drifted out onto the sidewalk. Moe himself held quiet authority behind the counter. Browsers moved slowly, as if time among books was time well stolen. He bought books fairly—no haggling, just a fair price—and held court with that cigar while the avenue hummed with protest outside.

Orlean might begin with affectionate observation: the smoke, the quiet authority, the browsers moving as if time were something you could borrow among the shelves. Didion would coolly note the cultural performance—the revolutionary texts amid fading energy. Thompson would immerse you in the sensory sanctuary, the myth of the place. Breslin would tell it like a guy at the bar: Moe buying books fairly, no nonsense, holding court with that cigar while the world outside churned.

Each approach turns the same details—cigars, fair dealing, the charged atmosphere—into something that hooks and reveals. What unites them is deep curiosity and receptivity: seeing people and places fully, with compassionate attention.

How to Get Good at Leads

Mastery comes from deliberate practice. Here are approaches I’ve found helpful:

  • Read and dissect. Keep a notebook of great leads. Note what emotion or curiosity they trigger and what promise they make.
  • Write multiples. For any story, draft five versions—zinger, scene, metaphor, question, quiet setup—then choose or combine.
  • Draft first, revise last. Write the piece, then craft the lead. Or iterate after you know the emotional core. Read aloud.
  • Hunt arresting details. Look for surprising combinations (Orlean) or telling contradictions (Didion). Your own memories are full of them.
  • Get feedback early. Share just the lead. Ask: Does this make you want to read more?
  • Experiment with constraints. Try ultra-short leads or imitate a master’s voice, then adapt to yours.

Over time this becomes instinctive. Leads force clarity about what your story really is.

Common Pitfalls

Avoid summaries that feel polite but boring, or cleverness that sacrifices clarity. The best leads align with your internal compass—generous, empathetic, curious. They reflect compassionate honesty: offering truth with care.

Writing better leads is one small way to live my life theme more fully. It’s about paying close attention, finding the spark in the everyday, and inviting others to do the same.

These values are my compass—and today, curiosity feels like the right direction.

Categories
AI Apple Google

The Library You Already Own

Sharon Park in the morning is not a dramatic place. There’s a duck pond, a stand of oaks that go gold too briefly in November, and a loop I’ve walked enough times that my legs know it better than my eyes do. It is, in other words, exactly the kind of place where a person starts talking to himself. Not out loud. In the productive, low-grade way — turning a sentence over, arguing with an idea from the day before, checking a thought against something you believe about yourself.

I think in five years I’ll be doing that walk with something else along. Not a search engine. Not another chatbot trained to know a little about everything and a lot about nothing in particular. Something closer to a second set of eyes on my own life — a reasoning engine, lean and mostly private, that has actually read the things I’ve written and doesn’t need me to explain who I am before it’s useful.

Here’s the distinction that matters, and it took me longer than it should have to see it clearly. The AI industry has spent years in an arms race over how much of the world a model can hold — more facts, more languages, more of the internet compressed into weights. That race will keep going, and somebody else can have it. What I want is smaller and stranger: a model that knows comparatively little about the world and quite a lot about me. My core values document. The portfolio spreadsheets. Fifteen years of blog posts. The half-finished notes for the I-280 project, sitting in a folder, waiting for someone — or something — to ask the right question about them.

I spent a career in payments infrastructure, which means I spent a career thinking about a very specific kind of trust: the kind where a stranger’s system has to make a judgment call, in milliseconds, about whether to say yes. Fraud models don’t work because they know everything about commerce. They work because they know an enormous amount about one account, one pattern, one person’s ordinary Tuesday — enough to notice when Tuesday stops being ordinary. That’s the architecture I keep picturing, aimed inward instead of outward. Not a system trying to know the world. A system trying to know me, well enough to notice when I’m drifting from what I said I cared about.

I can already feel the shape of the mornings this would change. Right now, when I sit down to look at RMD requirements against the tax picture, I’m doing the translation myself — pulling numbers into a story I can actually feel the weight of. A reasoning engine grounded in my real holdings wouldn’t just run the scenario. It would know that I don’t want the scenario dressed up as a spreadsheet; I want it dressed up as a conversation, unhurried, the kind you’d have over lunch with someone who already knows the whole situation. And on the mornings when I sit down to write, instead of staring at a blinking cursor and a blank page that has no idea I exist, I’d be handing a draft to something that has actually read my last two hundred posts and knows the difference between the sentence I’d write and the sentence I’d cut.

None of this is especially exotic technology. Apple and Google are already building toward it — Neural Engines fast enough to do real reasoning on-device, retrieval systems that can reach into your own files instead of the entire internet, fine-tuning that’s getting cheap enough to personalize rather than merely customize. The more interesting story here isn’t privacy, though privacy is real. It’s architectural: what happens when the expensive, impressive part of the system — the part that knows everything — becomes optional, and the cheap, personal part — the part that knows you — becomes the whole point.

What I don’t yet know is what this will cost me. A tool that reasons this well about my own life is also a tool I could lean on instead of doing the leaning myself, and there’s a version of this future where the walk around Sharon Park stops being mine and starts being a conversation with something that finishes my sentences a little too well. I’d want some way of knowing, plainly, what it’s drawing from and what it’s guessing at — less a nutrition label than a kind of honesty I could check against, the way you’d check a fraud model’s confidence score before you trusted it with a yes.

But most mornings, I think I’d take the trade. Not because I want to think less. Because for thirty years I’ve been collecting the raw material — the notebooks, the portfolios, the half-built essays — and it would be something, finally, to walk beside a mind that had actually done the reading.

Categories
AI: Diffusion Models Art and Artists

An Algorithm by Hand

He didn’t know what he was looking for the first time he walked into the Alhambra. You come in from the heat and the light hits the walls and for a moment you just stand there, your mind doing something it doesn’t have words for yet.

That was 1922. Escher was twenty-four years old, recently graduated. The Moorish artists who made these walls had been dead for six centuries. They had left no notes. No theory. Just the walls.

He came back in 1936. Some things you have to see twice.

What the artists in the Alhambra had discovered — without algebra, without proof, working in a tradition that forbade them from drawing a single living creature — was that there were exactly seventeen ways to tile an infinite plane with a repeating pattern. The Russian mathematician Fedorov would articulate this formally in 1891, centuries after the fact, the way mathematics sometimes chases art home and explains what it already knew.

Escher took the problem and made it harder. He asked: what if the edge between two tiles is also the outline of a fish? What if the sky is made of birds and the birds are made of sky? He would move a single line and the whole system would tremble. He did this for years. Revision after revision, in small notebooks, by hand.

There is a word for what he was doing. We just didn’t have it yet.

The word is algorithm.

An algorithm is a set of rules, followed in sequence, to solve a problem. We think of them as things that live in machines, in data centers drawing enough power to light a city. We think of them as fast. Escher’s algorithm was not fast.

He would begin with a grid. Hexagons, maybe, or the interlocking diamonds of a pattern he had traced from the Alhambra walls. Then he would ask the question that made everything hard: what lives here? Not what shape — what creature? What thing with a spine and a purpose and an outline that a human eye would recognize before the brain caught up?

The constraint was absolute. Every point on every edge had to satisfy two animals simultaneously. Change one line and you changed everything downstream, the way a single altered fact in a long investigation suddenly makes you reread everything you thought you knew.

He failed constantly. The notebooks are full of it. Half a lizard becoming nothing. A bird whose wing destroyed the fish below it. He would back up and try again, the way you back up on a road that has stopped being a road.

He was doing, neuron by neuron, what a diffusion model now does in milliseconds.

But here is the thing about milliseconds. They don’t leave notebooks.

Categories
Writing

The Grain Bin and the Ghost

Richard Rhodes published How to Write in 1995. In it, he offers practical advice about a writer’s reference shelf: keep a dictionary at home, own a one-volume encyclopedia. He mentions, almost in passing, that he just received the OED on CD-ROM as a birthday gift.

That sentence stops you cold in 2026.

Not because it’s quaint — though it is — but because of what it reveals about how a writing life was organized. Rhodes wasn’t describing luxury. He was describing infrastructure. The reference shelf was load-bearing. You kept facts at home the way you kept food in a pantry: because access wasn’t guaranteed, because the library closed, because the gap between not-knowing and knowing could be measured in trips and hours. A writer’s bookshelf was a personal hedge against scarcity.

Think about what it meant that someone’s birthday present was a reference tool. Not a novel. Not a bottle of wine. Twenty volumes of the most authoritative dictionary in the English language, compressed to a disc, given because a writer needed it and couldn’t otherwise have it on their desk. That’s what a writing life cost. That’s what it demanded of the people around you.

That scarcity is gone so completely it’s hard to reconstruct the phenomenology of it.

The bottleneck in Rhodes’s world was access. You either had the fact or you didn’t. Getting it required physical movement — to the shelf, to the library, to someone who knew. The reference book’s value was proximity: it collapsed the distance between the question and the answer. The OED on CD-ROM was remarkable precisely because it put those twenty volumes on your desk. No trip. No waiting. That was the gift.

The bottleneck now is entirely different. Access is solved, trivially, for anyone with a phone. The question isn’t where the facts are. The question is which facts to trust, how they were assembled, whether the source has an agenda, whether the model that synthesized them has introduced drift. We moved from a scarcity problem to a judgment problem, and most of our inherited intellectual habits were built for the former.

But something else happened too, something Rhodes couldn’t have framed because it didn’t exist: the infrastructure became generative. The reference shelf held facts. It didn’t think with you. It didn’t draft alongside you, or push back on your argument, or notice that the claim you just made contradicts something three paragraphs earlier. The CD-ROM OED was static; it waited to be consulted. The tools a writer reaches for now don’t wait. They participate.

This is the structural shift that the grain bin metaphor can’t contain. Rhodes was describing a writer’s relationship to stored knowledge — how you accumulate it, how you keep it close, how you move through it when you need it. That relationship was essentially curatorial. You built a collection. You maintained it. You drew from it.

What’s emerging now is something more like a collaboration with an infrastructure that has opinions. Not always right ones. Not always trustworthy ones. But opinions nonetheless — which means the writer’s job has changed in kind, not just in degree. You’re no longer managing a pantry. You’re managing a working relationship.

Where does it end up? Probably somewhere Rhodes would recognize at the level of the goal — clarity, the right word, the true sentence — and find almost unrecognizable at the level of method. The shelf is still there. But it talks back now. And figuring out what that means — whether to trust it, when to push against it, how to stay the one doing the writing — is the work no one has finished yet. Maybe no one can, while it’s still changing this fast.

Categories
Aging AI Business Living

The Being Phase

There is a metric making the rounds in technology investing circles that is, on its face, about market share and revenue concentration. Alex Sacerdote of Whale Rock Capital calls it the New Rule of 40 for AI. The formula is simple: take the percentage of a company’s sales derived from AI, add its percentage market share in that AI category, and if the sum reaches 40, you have a winner. Celestica, a company most people have never heard of, scores extraordinarily well. It owns somewhere between half and sixty percent of the cloud Ethernet white-box switch market. NVIDIA doesn’t need a formula. It simply is what it is.

Sacerdote designed the metric to cut through a specific kind of noise — the companies claiming AI exposure they don’t actually have, the giants whose AI revenue hovers at one or two percent of their base while their press releases suggest otherwise. The framework is a detector. It finds the companies that have stopped becoming AI infrastructure and started simply being it.

I found myself less interested in the companies than in that distinction.

I spent years at Visa watching a network that had long since crossed that threshold. By the time I arrived, Visa wasn’t becoming the global payments infrastructure. It was the global payments infrastructure. The work was real — fraud detection, modeling, the daily labor of keeping something enormous running — but the existential question had been settled before I got there. The network existed. Merchants accepted it because cardholders carried it. Cardholders carried it because merchants accepted it. That loop had been closing for decades. We were custodians of a fait accompli.

There’s a particular feeling to working inside something that has already won. It’s not complacency exactly. The problems are genuine and the stakes are high. But the uncertainty has a different quality — it’s operational uncertainty, not existential uncertainty. You’re not asking whether the thing will survive. You’re asking how to run it well.

I didn’t have language for that distinction then. Sacerdote’s metric gives me some. The companies that score highest on his New Rule of 40 have resolved their existential question. They’re not fighting for position. They’re administering a position already held.

The question that has followed me out of that career, and out of several decades of watching technology cycles turn, is simpler and more personal than any investment framework.

When did I cross that line myself?

I have been writing at sjl.us since 2001. That’s not a boast — it’s a data point. Twenty-five years of thinking out loud, of ideas arriving rather than being argued, of the specific memory as structural anchor. The blog is not becoming anything. It is what it is: a record of a mind moving through time, accumulated into something that has its own weight and shape.

The book on payments systems exists. The career at Visa exists. The photographs exist. The train journeys exist. The years in Dayton exist, and the years on the Peninsula, and the particular way the light falls on the California coast at Pescadero in the late afternoon — when the fog is still offshore and the hills are improbably green and everything goes briefly, completely quiet, as if the world is deciding whether to continue.

These are not things I am building toward. They are things I am.

Sacerdote would say I have high market share in a specific category. The category is small — one person, one particular configuration of experience and attention and accumulated knowing — but the share is essentially total. There is no competitor for the position of having lived this particular life. The moat is absolute. The switching costs are infinite.

I used to find that thought melancholy. The narrowing as loss. The aperture closing on what remains.

I’m not sure I find it melancholy anymore.

The L-Curve, Sacerdote says, is a long flatline followed by a vertical explosion. The tinkering phase, then the moment of lift. He means it as a description of demand curves for technology infrastructure. But I recognize the shape from somewhere closer. The long middle of a life, building and becoming, and then the morning you wake up and realize the building is substantially done. What remains is the being.

That’s not an ending. It’s a different kind of beginning.

Sacerdote’s metric will eventually stop working. All frameworks do. The AI infrastructure cycle will mature, the L-Curves will flatten, and some new measure will emerge to find the next thing that is just beginning to become what it will be. That’s the nature of markets. The detector has to change as the signal changes.

But there’s a complication worth naming. Analysts at Citadel Securities published a note recently observing that even the most powerful technologies must pass through the prosaic discipline of cost curves, capacity constraints, and marginal returns. Token bills are arriving unexpectedly. Compute is scarce. The vision of AI as ubiquitous, frictionless, and immediate is colliding with physical reality. Their conclusion: asset prices will periodically be forced to reconcile ambition with physical constraint.

That’s not a refutation of Sacerdote. It’s a reminder that feeling like you’ve arrived and having actually arrived are different things. The being phase has to be load-tested. The position has to hold under pressure.

I think about the fiber optics Corning is laying into the massive data center clusters — ultra-thin, bendable, carrying more light than anything that came before. The cable doesn’t know it’s infrastructure. It just carries what it’s given, at the speed it’s capable of, across whatever distance is required. It doesn’t matter what the cable believes about itself. What matters is whether the light actually moves.

That seems right to me. You become what you are over a long time, largely without noticing. And then one day someone builds a metric that accidentally describes your life, and you recognize yourself in it, and you think: yes. That’s the shape of it. High concentration. High share. A moat that deepened while you were looking elsewhere.

But the moat still has to hold.

The being phase, it turns out, is not the end of something. It’s the proof that something was built. And the daily question — for companies, for infrastructure, for a person in his late seventies still writing, still paying attention — is whether what was built is actually load-bearing.

You don’t get to stop finding out.

Categories
Writing

Still Learning

I never thought about rhythm in my writing. Not once.

A lifetime of writing. More essays than I can count. One book. And the sonic quality of my sentences — the way they moved, or failed to move, through a reader’s mind — simply wasn’t something I considered. I was too busy trying to say something true. I thought that was enough.

What changed was reading differently. Not for pleasure anymore, or not only for pleasure. David Perell conducts long interviews with writers about how they actually work — not what they believe about writing, but what they do, physically, at the desk, in the dark, before anyone sees it. He asks the same structural questions of very different writers and the patterns emerge slowly, the way patterns always emerge: first you see it once and think nothing of it, then you see it again, then you can’t stop seeing it. Rhythm came up constantly. Always in different language. Pacing. Breath. Music. Momentum. Always pointing at the same thing.

Then I found this from Susan Orlean:

My new preoccupation was on the sonic quality of my writing — the rhythm and tone of the sentences. I began reading all my work out loud, listening for places that lagged and dragged, that didn’t sparkle. I knew it was unlikely that anyone else was reading my stories out loud, but I was convinced that you do “hear” writing in your head as you read, and this pushes you (or stalls you) through the piece. I wanted the music — that is, this subconscious tonal effect — to match the subject.

I stopped. Read it again.

Because she was describing something real — something I had been doing wrong for twenty-five years without knowing it was wrong. You don’t know what you can’t hear. That’s the whole problem. The silence where the knowledge should be is itself silent.

I don’t read my work out loud. There’s something strange about it, something that breaks the spell — you stop being a writer and become an actor, hearing your own sentences hanging in the air, too exposed. But I do read and read again, more carefully now, looking for the wobble. Orlean’s point holds regardless of method: you hear writing in your head as you read it, and that hearing either carries you forward or it doesn’t. The ear that matters is the one inside.

George Saunders has a practice he describes in A Swim in a Pond in the Rain: he reads from the beginning of a piece over and over, and the moment something feels off — a word, a rhythm, a single syllable landing wrong — he stops and fixes it before moving forward. Never skips the trouble spot. Never tells himself he’ll come back. His opening pages accumulate dozens of passes before he ever reaches the end. What he’s really doing, underneath the technique, is training himself to feel the exact microsecond when a reader’s attention would start to drift. To catch the loss before it happens.

That’s not craft instruction. That’s building a new sensitivity where there wasn’t one before.

John McPhee works from the other direction entirely. His famous boxes — index cards, sorted into piles, piles arranged into sequences, nothing drafted until the structure is known — are about architecture before a single word is written. He’s deciding which rooms exist, and in what order, before he furnishes any of them. Where Saunders builds outward from one true sentence, McPhee builds downward from a blueprint.

But they’re asking the same question. McPhee: is this section in the right place? Saunders: is this word in the right place? Both listening for the moment the piece loses its hold on the reader. Both doing triage on something most writers never even examine.

What I’m still learning — slowly, and late — is that rhythm isn’t decoration. It isn’t the thing you tend to after the real work is done. It’s structural. A sentence moving at the wrong speed for what it’s carrying fails the thought itself, not just the ear.

There’s something else I’ve been thinking about. If rhythm is the thing that’s hardest to hear in your own work — if the ear takes years to develop — then maybe the most useful writing tool isn’t a grammar checker. Those are solved. What isn’t solved is the rhythm problem. An editor who listens for the wobble, explains what’s failing and why, and works through the fix with you rather than just patching it. Not a red pen. A teacher.

I’ve been experimenting with exactly that. An AI editor I call Clark. His job isn’t correctness. It’s the sonic quality of prose — the rhythm — the same thing Orlean was describing, the same sensitivity Saunders spent years training. Clark finds what’s working as hard as what isn’t. And when something fails, he explains what the reader’s inner ear is hitting and why. Helpful.

I didn’t know much about rhythm in writing when I was fifty. Didn’t know it at sixty.

I’m not entirely sure I know it now. But I know it more than I did, which might be the only kind of knowing that’s real.

A lifetime of writing. Still learning how to listen.

Categories
Creativity Photographers Photography Serendipity Writing

He Taught Us How to See

Michelangelo said he didn’t create his sculptures. He just removed the marble that wasn’t the statue.

I’ve been thinking about that lately. About what it means to have a collaborator whose job isn’t to add things but to help you find what’s already there. I’ve been doing that kind of work recently — the excavation kind — and it has changed how I write and honestly how much I enjoy the making of it.

But I’m getting ahead of myself. Start with Jay.

Continue reading “He Taught Us How to See”
Categories
Living Serendipity

The Infrastructure of Accident

I had a ham shack when I was in high school. A tight corner of my bedroom, a transceiver, an antenna wire running out through the window frame to somewhere up on the roof. Late nights mostly. The ritual of it: power on, headphones on, find a frequency, make sure it’s clear. Then send CQ. CQ. CQ. A call to no one in particular, to anyone, to whoever happened to be listening on that frequency at that moment anywhere on earth.

Sometimes nothing came back. Sometimes someone answered from a place I had no reason to expect — a voice, or rather a pattern of dots and dashes that resolved into a voice, from a callsign I didn’t recognize, from a grid square I’d have to look up on a map afterward. We would exchange signal reports and names and locations and often we talked longer. Our gear. What we did that day. Ordinary things, transmitted at forty words a minute across a great distance to a stranger I would never meet.

I did not know then that I was practicing something. I thought I was just playing radio.

We have decided, sometime since, that luck is a system. That serendipity is an architecture. That the people to whom good things happen have engineered the conditions for good things to happen, and that the people to whom good things do not happen have, at some level, failed to present the right surface to the world.

I am not sure when we decided this. Sometime after we stopped believing in fate and before we started believing in algorithms, in that narrow window when we still believed, provisionally, in ourselves.

The self-help literature on luck is a literature of verbs. Expand. Broadcast. Reframe. Sabotage your algorithms. The verbs are always active, always transitive, always aimed at a future in which the random becomes, retroactively, inevitable. You will look back and see the architecture. You will understand that the flight delay was an opportunity, that the canceled meeting was a gift, that the stranger in the adjacent seat was not a stranger at all but a node in a network you were already, without knowing it, building.

What the literature cannot account for is the canceled meeting that was simply a canceled meeting. The flight delay in which nothing happened except that you sat in a molded plastic chair in Terminal B and ate a sandwich that cost fourteen dollars and thought about everything you had not yet done. The stranger who remained a stranger.

I have been thinking about a used bookstore on Telegraph Avenue in Berkeley, at the corner of Dwight. Shakespeare & Co. It smelled the way all serious used bookstores smell — dust and possibility, which are not always different things. The shelves ran floor to ceiling and were not organized in any way that rewarded efficiency. You found things there the way you find things in dreams: without looking, and then suddenly they were in your hands.

I found a paperback copy of Slouching Towards Bethlehem there. Someone else’s margin notes in blue ink, a handwriting I did not recognize and have never been able to stop thinking about. Whoever they were, they had underlined the same sentences I would have underlined. They had written yes in the margin next to things I did not yet know I believed.

I have no way of knowing whether that was luck or whether I had simply been the kind of person who wandered into bookstores and stayed too long. The kind of person for whom that particular door was already, structurally, open.

Buildings have architects. Someone drew the plans. But I cannot find, looking back, the moment I became that person. I can only locate the book.

The word serendipity was coined in 1754 by Horace Walpole, who derived it from a Persian fairy tale about three princes of Serendip who were always making discoveries by accidents and luck, of things they were not in quest of. Accidents and luck. The word has always contained both. What the contemporary literature has done is quietly eliminate the accident and keep only the luck — reframed now as preparation, as readiness, as optimized openness. The princes were not prepared. They wandered.

Anymore we are often uncomfortable with just wandering. Wandering has no metrics. A waste of time.

There is a thing that happens when you pick up a physical newspaper, one you did not choose from a menu of personalized recommendations online but simply lifted from a rack at the library because it was there. You read stories you would never have clicked on while reading on an iPhone. Not because you lacked interest but because no algorithm had yet determined that you had it. The story finds you before the system can decide whether you are the kind of person who would want to be found.

I go to the library some days for precisely this reason. It is a considered refusal — the same one the princes of Serendip were practicing, though they had no word for what they were refusing. The library does not know what I clicked on last Tuesday. It cannot optimize my morning. It can only offer everything, indiscriminately, and trust me to wander.

Life feels richer on those days. I have tried to understand why and have arrived, after some time, at this: on those days the world is larger than my prior assumptions about it. That is not a small thing. That may, in fact, be the whole thing. Here comes the sun!

Shakespeare & Co. closed in June 2015, after fifty-one years on Telegraph Avenue. The owner said the past few months had been unsupportable. He taped a note to the door and served his last customer and locked up around eight in the evening and that was that. Someone who worked there was quoted saying that the serendipity of finding a book that changes your life doesn’t happen on Amazon. Indeed. He meant it as an elegy. The infrastructure of accident had to be built by someone. It had to be maintained. It had to be, on some Tuesday evening, locked for the last time.

The owner locked up around eight. He had served his last customer. There was nothing more to do.

The margin notes are still in the book.

Categories
Storytelling Writing

The Craft in the Work: A Reading Guide to Ten Storytellers

There’s a kind of reading that’s really a form of listening — not to what a writer is saying but to how they’re solving a problem. Every great piece of nonfiction is an argument about structure, and most writers never explain it aloud. The argument is in the choices: where the piece starts, when it digresses, what it leaves out, how it ends. You can enjoy the work without seeing any of this. But once you start seeing it, you can’t stop — and eventually, some of it becomes yours.

This guide is for both kinds of reading. Each writer here is worth your time as a reader. Each one also has something specific and stealable for anyone who writes. I’ve tried to name both.

The ten: John McPhee, Robert Caro, John Jeremiah Sullivan, Michael Lewis, Joan Didion, David Grann, Sam Anderson, Susan Orlean, Tom Junod, and Wright Thompson. Different registers, different obsessions, different methods. What they share is a commitment to making difficult things feel inevitable — and the discipline to make that look effortless.

They fall into three loose clusters, which might help you find your entry point. Structure builders — McPhee, Caro, Grann — write pieces that feel inevitable because the architecture is invisible but load-bearing. Emotional access — Orlean, Junod, Thompson — get you inside feeling before you know you’re there. Voice and form — Didion, Sullivan, Lewis, Anderson — the sentence, the digression, the explanatory seduction, the essay as genuine inquiry. The clusters overlap, and the best writers in each group are doing all three things at once. But if you’re trying to solve a specific problem in your own writing, the clusters tell you where to look first.

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The Starting Five I Keep

On November 25, 1963, every journalist in America was at Arlington Cemetery covering the state funeral of John F. Kennedy. Jimmy Breslin went to find the grave digger.

His name was Clifton Pollard. He was paid $3.01 an hour. He had been called in on his day off because the foreman thought he was the best they had, and the foreman was right about that. Breslin spent the morning with him while the ceremony unfolded a few hundred yards away — the dignitaries, the riderless horse, the flag folded into a triangle and handed to a widow. Pollard ate a ham sandwich and kept working.

The piece Breslin filed that afternoon is still taught in journalism schools sixty years later. Not because it covered the funeral better than anyone else. Because it didn’t cover the funeral at all. It found the true subject by ignoring the announced one.

That instinct — turn away from the obvious, walk toward the unglamorous specific, trust that the universal is hiding there — is the one idea I’ve returned to more than any other. It shows up in two very different writers who occupy, in my mind, the same position on the roster.

Breslin got there through deadline fury and a saloon-bred instinct for where the real story was breathing. He didn’t theorize about it. He just did it, on a deadline, in a city that rewarded the loud and the fast. John McPhee got to the same place by an entirely different route: patience, structure, and a willingness to spend six months learning how canoes are made or what happens to a piece of shad on its way up the Delaware River. Breslin worked like a man catching a cab. McPhee worked like a man building a cathedral.

But the underlying claim is identical. If you stay with a specific, unglamorous subject long enough — if you resist the pull toward the obvious center — it will eventually yield something that couldn’t have been reached directly. Pollard and his shovel. The orange grower and his grove. The nuclear physicist who also happens to be a canoe builder. The method is the same. Look where no one else is looking. Wait longer than feels reasonable. Write what you find.

This is one player, really. Just wearing two different jerseys.

The second seat belongs to Wright Thompson — not a single book but a stance. The premise that the most revealing place in any story isn’t the event itself but the moment before and after it, when the subject is alone with something they haven’t yet put into words. Every piece in this tradition is quietly asking: what is this person carrying that they can’t say out loud? It’s a question that turns out to apply well beyond sportswriting. It applies to most things worth writing about.

The third is whatever the Apple design era taught about constraint and clarity. Not nostalgia — something more durable. The idea that removing something can be an act of confidence. That the most useful things often appear to be doing less than they are. This one surfaces constantly in writing, in argument, in the editing pass where you decide what the piece actually needs versus what it accumulated along the way. Features are easy to add. Knowing what to cut requires a different kind of certainty.

The fourth is the philosophy embedded in spaced repetition — not the algorithm but the claim underneath it. That knowledge you don’t revisit isn’t really yours. That understanding decays on a predictable schedule whether you acknowledge it or not. The honest response isn’t anxiety about this; it’s the habit of return. Going back to the same passage, the same idea, the same question on a different day, and finding it has changed — or finding that you have.

The fifth seat shifts. That’s probably the right design. Four constants and one that evolves is roughly the correct ratio for a starting lineup that has to play in different eras. Right now that seat belongs to the question of what AI does to a practiced human sensibility — whether it erodes it by substitution or clarifies it by contrast. Earlier it was held by a certain kind of systems thinking. Before that, something else. The player who earns that spot is always the one asking the question the current moment most needs answered.

The coach who wins five championships doesn’t do it with the same roster. But he does it with the same philosophy. The starting five aren’t the players who happened to be good once. They’re the ones who keep earning their minutes regardless of what the season throws at you.

Breslin knew where to find Clifton Pollard because he’d been looking in that direction his whole career. The skill wasn’t the story. The skill was knowing that the story was never where everyone else was standing.

That’s the one I keep coming back to.