Tag: storytelling

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.

Continue reading “The Craft in the Work: A Reading Guide to Ten Storytellers”
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
Writing

The Unfinished Note

I’ve been sitting with a Susan Orlean line for a few days now, the way you sit with a splinter you can’t quite locate.

“Stories don’t need a ‘conclusion,’ a flourish of finality. It’s better to leave readers falling forward, tumbling through the piece and beyond it, finishing the tune in their heads.”

What strikes me isn’t the advice — plenty of writing teachers have said something like it — but the verb she chose. Tumbling. Not drifting. Not lingering. Tumbling. There’s a loss of control in that word, a small helpless momentum, the way you take one more step than you expected on a dark staircase and your body has to catch up to itself.

I’ve always been suspicious of endings that arrive wearing their own bow. You can feel them coming, those last paragraphs — the rhythm slows, the sentences get more declarative, the writer seems to straighten up and clear their throat. And then comes the lesson, the restatement, the turn toward uplift or hard-won wisdom. The piece explains what it was about. You close the browser tab and that’s the end of it.

But some pieces don’t end so much as they stop, at the right moment and the right angle, and something in you keeps moving. You find yourself thinking about them in the shower two days later. You’re not remembering the conclusion because there wasn’t one. You’re still inside the piece, finishing the tune, as Orlean says. The writer handed you the melody and walked off mid-phrase.

I think about this with music. Jazz, especially. The best solos don’t resolve — they suggest a resolution and then leave the air charged with it. Miles Davis understood that the note you don’t play is still a note. The silence after the phrase is part of the phrase.

I’m not sure I’ve ever actually written an ending this way. Most of my pieces come in for a landing; I can feel myself starting to circle and descend. Maybe that’s the real lesson in Orlean’s line — not a craft note about structure, but a challenge to trust the reader enough to leave the door ajar. To believe the piece was good enough that they’ll want to keep walking around inside it.

I’m still not sure I do.

Categories
Storytelling Writing

The Nerve of the Opening Line

For years I wrote first paragraphs that explained what I was about to say, which is a little like a joke that begins by describing how funny it is.

Susan Orlean has a better idea. In her book Joyride, she writes that a lede doesn’t need to preview the story or summarize what the rest of the piece will be about. What’s important is that it captivates readers and holds them fast to the page so they keep reading.

The conventional wisdom about ledes is that they exist to tell readers what they’re about to read. The billboard theory of the opening. Here is what this story is. Here is why it matters. Here is what you’ll find if you continue. The lede as table of contents, compressed.

Orlean is saying something stranger and more honest: the lede’s job is not to inform. It’s to hold the reader.

There’s a distinction there worth sitting with.

Informing a reader is a transaction — you transfer content, they receive it. Holding a reader is something else entirely. It’s closer to what a magician does in the first thirty seconds of a performance, or what a stranger does when they say something at a party that makes you turn and face them fully. You haven’t learned anything yet. You’ve just been made to stay.

The ledes that have held me longest tend to have almost nothing to do with the stories they open.

Joan Didion begins “The White Album” with a single sentence — “We tell ourselves stories in order to live” — that takes the entire essay to even partially fulfill.

Gay Talese opens his Frank Sinatra profile not with Sinatra’s voice or his legend but with a man going silent: “Frank Sinatra, holding a glass of bourbon in one hand and a cigarette in the other, stood in a dark corner of the bar between two attractive but fading blondes who sat waiting for him to say something. But he said nothing.”

Tracy Kidder opens The Soul of a New Machine not with computers but with a boat in a storm, Tom West awake for four straight nights while everyone else is seasick, the rest of the crew left wondering what on earth this man does for a living.

None of these ledes summarize. All of them hold.

What they share, I think, is a quality of disturbance. They’ve moved the ground slightly underfoot. Something is tilted.

Didion’s first sentence argues that we tell ourselves stories in order to live, and you feel the vertigo in it immediately — wait, is that true? Is that a good thing or a desperate thing?

Talese gives you a man diminished by illness and silence, and everything that follows is measured against that diminishment.

Kidder’s boat goes somewhere that prose about minicomputers wouldn’t, and by the time you’ve crossed that dark water with West, you’re already a different kind of reader than you were on page one.

I think about this when I try to write.

I grew up reading ledes the billboard way — I thought the first paragraph was a promise about what the reader would receive. And sometimes I still write them that way, which is to say I write them first and delete them later, because they’re stage fright disguised as generosity. Here is what I’m about to tell you really means please don’t leave before I find my footing.

The Orlean formulation — captivate, hold, keep reading — shifts the pressure off the writer’s anxiety and onto the reader’s experience. The question is no longer what do I need to tell them? The question is what will make them unable to leave?

That’s a harder question. It requires knowing something about what people can’t resist. Strangeness. Motion. A body in trouble. A door left open. The suggestion that someone knows something you don’t.

The best ledes I’ve ever written didn’t come first. They came after I’d already written the whole piece and finally understood what it was actually about — which turned out not to be the thing I thought it was about at the start. You can’t write the sentence that makes someone stay until you know what you’re asking them to stay for.

The lede isn’t a promise. It’s a wager. You’re betting that the reader will follow disturbance into the dark — and the only way to make that bet is to trust the disturbance yourself first. Most of us don’t. Most of us write the billboard because we’re afraid that if we don’t explain what’s coming, the reader will leave.

But the reader doesn’t leave because they’re confused. They leave because nothing reached out and held them.

The explanation never does that. The strangeness might.

Categories
Living Writing

The Origami Swan

Fold a piece of paper enough times, and it begins to take shape. It looks like a swan, but it isn’t one. It’s origami. Two-dimensional paper masquerading in a three-dimensional world.

There is a profound danger, both in writing and in how we move through life, of viewing people as origami. We see the folded edges—what they do, what they say, where they go—and we mistake the shape for the substance.

The sportswriter Wright Thompson borrows a concept from a college Tennessee Williams class to describe what is missing when we do this: interiority. It is the subterranean emotional reality happening beneath the visible actions of a character. Without it, scenes are flat. Without it, people are just paper swans.

Thompson builds on the philosophy of Gary Smith, who argues that every profile fundamentally asks the same question: What is the central complication of this person’s life, and how do they go about solving it every single day?

Almost all of that solving happens quietly, invisibly, on the inside. The exterior architecture of a person’s life is entirely meaningless until you understand the interior architecture holding it up.

But how do you communicate something so deeply internal? You can’t just tell the reader what someone is feeling. It feels cheap, unearned. Instead, Thompson uses a technique of “loading the object.” You find an exterior detail—a habit, a possession, an avoidance—and you charge it with interior meaning.

“The exterior action… is only meaningful if you’ve built the interior architecture first.”

Consider Michael Jordan. Thompson learned that Jordan falls asleep to old Westerns. As an isolated fact, it’s just a quirky celebrity habit. But Thompson also learned that Jordan misses his murdered father every single day, and that watching Westerns was something they used to do together.

By introducing the Westerns early and casually, Thompson loads the object. By the end of the piece, when he simply describes Jordan falling asleep to a Western, he doesn’t need to explain the grief. The reader already carries the emotional weight of the object. A completely mundane action becomes devastating.

The same is true of Tiger Woods naming his boats Privacy and Solitude. To the casual observer, they are just wealthy indulgences. But once you understand the interiority of an extreme introvert who has been force-fitted into a global, extroverted marketing machine since childhood, those names are no longer just names. They are a diagnosis.

Executing this requires two distinct disciplines. The first is deep observation—what journalists call reporting. You cannot manufacture interiority at the keyboard. As Thompson notes, whenever a scene feels flat, it is because he hasn’t dug deep enough into the reality of the person to earn the meaning. Overwriting is simply underreporting with a better vocabulary.

The second discipline is restraint. Once you have built the interior context, you must stop talking. You have to let the exterior action land in silence. The human instinct is to over-explain, to ensure everyone gets it. But the magic happens when you step back and trust the connection you’ve built.

There is a philosophical lesson here that extends far beyond writing. How often do we settle for the origami versions of the people around us? How often do we try to talk our way into understanding them, rather than doing the deep, quiet work of observing their “loaded objects”?

To truly understand another human being requires the discipline to look past the surface, the patience to uncover their central complication, and the grace to let their quietest moments speak for themselves.

Note: Be sure to watch this conversation between Wright Thompson and David Perell.

Categories
Authors Storytelling Writing

The Architecture of Resonance

There’s a particular kind of madness that strikes writers late at night, or in the stagnant hours of mid-afternoon, when you find yourself staring at a single sentence for twenty minutes.

You’re weighing a semicolon against an em dash. You’re wondering if “murmur” is too soft or if “whisper” is too cliché. All of this while knowing, with complete certainty, that no reader will ever stop to appreciate this specific choice. They’ll just read the sentence and move on.

So why do we do it?

In Draft No. 4, John McPhee — the legendary literary journalist who spent decades at The New Yorker — shares a principle he still writes on the blackboard at Princeton. It’s actually a quote from Cary Grant: “A Thousand Details Add Up to One Impression.” The implication, McPhee explains, is that almost no individual detail is essential, while the details as a whole are absolutely essential.

I find this idea endlessly useful. And a little reassuring.

Think about walking into a beautifully designed home. You don’t notice the precise angle of the crown molding or the specific undertones of the paint. You don’t walk in and say, “Ah yes, Alabaster White.” You just feel warmth, or elegance, or comfort. The impression is singular — but it’s entirely built from a thousand invisible decisions someone made before you arrived.

Writing works the same way. The rhythm of your sentences, the specificity of your verbs, the way a paragraph ends — these are the details. Individually, they’re expendable. Swap “murmur” for “whisper” and the piece survives. Delete the semicolon and the world keeps turning.

But collectively, they are the piece.

Start compromising — reach for the easy cliché, let a clunky transition slide, settle for vague where you could be specific — and the foundation slowly rots. The reader won’t be able to name the moment they lost interest. They’ll just close the tab. The impression shifts from resonant to flat, without anyone quite knowing why.

Writing, then, is an act of quiet faith. It asks you to labor over things no one will applaud. Nobody claps for an em dash. But the work isn’t really for applause — it’s out of respect for the whole.

We curate a thousand invisible things so the reader can feel one visible truth.

So the next time you’re agonizing over a single word at midnight, remember: you’re not just picking a word. You’re placing a tile in a mosaic. Cary Grant understood it. McPhee put it on a blackboard. You might as well make it count.

Categories
Blogs/Weblogs Writing

Notes for a Distant Shore

I spend an embarrassing amount of time trying to control how people hear me. Most of us do. We want to be understood, neatly categorized, and told we make sense. But sitting down to actually write and sharing publicly requires dropping all of that. You just have to surrender.

Richard Rhodes nailed the feeling:

“To write is always to seal notes into bottles and cast them adrift at sea; you never know where your notes will drift and who will read them.”

You’re basically bottling up whatever is rattling around in your head on a Tuesday afternoon, tossing it into the digital ocean, and walking away. It’s vulnerable. Honestly, it’s a little reckless.

Once the bottle leaves your hand, you lose your voice. You can’t tap the reader on the shoulder to explain what a sentence really meant. The person who finds it brings their own weather to the shore. They might read a lifeline into a paragraph you barely thought about, or miss your main point entirely because they were distracted by the tide.

Forget about engagement metrics. The connections that actually matter rarely show up on a dashboard anyway. You write something, and it drifts. Maybe for years. Then someone stumbles over it exactly when they need it. You aren’t writing for a demographic; you’re writing for some random person walking the beach. True serendipity.

In the end, you just have to trust the water. Even if the bottle sinks, the act of throwing it is usually satisfying enough.

“Write as if you were dying. At the same time, assume you write for an audience consisting solely of terminal patients. That is, after all, the case. What would you begin writing if you knew you would die soon? What could you say to a dying person that would not enrage by its triviality?” (Annie Dillard, The Writing Life)

Categories
Books Writing

The Secret Handshake

Author George Saunders has a gift for articulating things you already knew but couldn’t say.

I was reminded of this recently when I returned to A Swim in a Pond in the Rain, his generous, luminous masterclass on Russian short fiction — the book that uses Chekhov, Turgenev, Tolstoy, and Gogol as a lens for understanding what fiction actually does to a reader, and why.

Early on, Saunders wonders whether there might be certain laws governing how we respond to stories — not rules handed down by writing programs, but something closer to instinct, something wired into the reading mind.

One of his candidates is physical description. “We like hearing our world described,” he writes. “And we like hearing it described specifically.”

That line stopped me. It has the quality of a truth that, once named, you begin seeing everywhere — in the books you love, in the passages you’ve underlined without quite knowing why, in the sentences that have stayed with you for years long after the plot has faded.

Plot pulls us forward. Character keeps us invested. Ideas give us something to argue with on the drive home. But it’s the specific physicality of a story that makes it land in the body.

“It was raining” barely registers. Tell me instead about raindrops beading on a leaf, or the way mud sucks at a boot heel with a wet shlup, and suddenly I’m not reading about a place — I’m standing in it.

Why should this be?

Saunders doesn’t fully explain it, and maybe the honest answer is that no one fully can.

Our brains are pattern-matching machines, wired by evolution to map territory and imagine consequence — and concrete detail feeds that machinery directly. Or maybe the explanation is simpler and more generous: we love the world, and hearing it rendered with precision is a form of praise.

Whatever the reason, the great writers have always known this law and obeyed it joyfully. With the help of AI I’ve collected a few good examples.

Consider the opening of Hemingway’s A Farewell to Arms:

In the bed of the river there were pebbles and boulders, dry and white in the sun, and the water was clear and swiftly moving and blue in the channels. Troops went by the house and down the road and the dust they raised powdered the leaves of the trees.

No grand metaphors. Just pebbles, dust, leaves, color, motion. Yet the scene is so tangible you can almost taste the grit. And the specificity does double duty — it grounds us in a real place while quietly foreshadowing the war that will eventually powder everything.

Dickens, who worked at a different scale entirely, goes symphonic with it. The opening of Bleak House is one of the great set pieces in the language:

Fog everywhere. Fog up the river, where it flows among green aits and meadows; fog down the river, where it rolls defiled among the tiers of shipping and the waterside pollutions of a great (and dirty) city… Fog creeping into the cabooses of collier-brigs; fog lying out on the yards and hovering in the rigging of great ships… fog cruelly pinching the toes and fingers of his shivering little ’prentice boy on deck.

The repetition is hypnotic, but it’s the specificity — cabooses, rigging, toes, pipes — that transforms weather into a living, malevolent presence. You don’t just read the fog. You feel it in your lungs.

Fitzgerald does something different again in The Great Gatsby, using the same technique to make moral decay feel physical and inescapable:

This is a valley of ashes — a fantastic farm where ashes grow like wheat into ridges and hills and grotesque gardens; where ashes take the forms of houses and chimneys and rising smoke and, finally, with a transcendent effort, of men who move dimly and already crumbling through the powdery air.

Ashes don’t just lie there — they grow, they form, they crumble. The grotesque precision turns an industrial wasteland into an image of everything the Jazz Age is trying not to look at.

And then there is Chekhov, who Saunders loves most of all. In “Gooseberries” — the story that gives Saunders his title — Ivan Ivanych plunges into a river in the rain:

He plunged into the water with a splash and swam in the rain, thrusting his arms out wide; he raised waves on which white lilies swayed.

Those white lilies swaying on the disturbed water — two words, one image — capture pure animal joy more vividly than any abstract declaration of happiness ever could. It’s the kind of detail that makes you want to jump in yourself.

Saunders is right.

Our reading minds light up at this stuff. Specific physical description isn’t decoration or craft-workshop virtue signaling — it’s the secret handshake between writer and reader. It says: I noticed this small, real thing. Did you?

In a world increasingly mediated by screens and summaries and the frictionless delivery of abstracted information, fiction’s quiet insistence on the pebbles and the fog and the lilies feels almost like an act of resistance. It insists that the world is worth looking at. That the particular matters. That rendering one thing exactly right is worth more than gesturing vaguely at everything.

So next time you’re reading — or writing — linger on the details. Describe the world specifically. Our hungry minds will thank you for it.

Questions to Consider

  1. Saunders suggests physical specificity might be a kind of law in fiction — something the reading mind responds to almost instinctively. Do you think this is universal, or culturally conditioned?
  2. The examples here are all from the Western literary canon. Does this law hold in traditions — Japanese, Russian, African, South Asian — that handle interiority and landscape differently?
  3. If our appetite for specific physical detail is partly evolutionary — the brain mapping territory — what does it mean that so much of what we now consume is deliberately abstract and summarized?
  4. Can over-specificity fail? Are there writers who pile on detail to the point where it stops doing its work?
  5. Saunders uses fiction to make the point, but does the same law apply to nonfiction, memoir, or long-form journalism — and if so, who are the writers doing it best right now?
Categories
Books

The Observer Observed

I first encountered Susan Orlean not in person, but in the ashes. Specifically, the ashes of the Los Angeles Central Library. Reading The Library Book was a masterclass in how to weave a forensic investigation with a love letter to a public institution. It was reportage, but it possessed a beating heart. She has spent decades at The New Yorker perfecting the art of the “curious observer”—the person standing just to the side of the frame, noticing the detail everyone else missed.

That is why picking up Joyride felt different.

In a memoir, the observer must finally step in front of the lens. The transition from The Library Book—which is about the preservation of collective memory—to Joyride—which is about the fluidity of personal memory—is a fascinating shift. When a journalist writes a memoir, there is often a tension. They are used to looking outward, hunting for the story in orchids or arsonists. Turning that gaze inward requires a different kind of bravery.

“A commute has a destination; a joyride has only a duration.”

The title itself suggests a specific philosophy of living. It implies that the movement itself is the point. As I read, I found myself thinking about the difference between navigating a life and simply driving through it. Orlean captures that distinct feeling of the wind in your hair, the blur of the scenery, and the realization that the “plot” of our lives is often just the things that happen while we are busy steering.

We read writers like Orlean not just for what they saw, but for how they saw it. In Joyride, she reminds us that the most interesting routes are rarely the most direct ones. A great read!

Categories
AI

Research Prompts

I recently came across a prompt in a post on X which has proven to be quite useful in brainstorming.

Here’s the prompt, tailored in this example to research the area of AI super intelligence:

You are a professional ghostwriter. Generate 15 high-signal content ideas on how AI labs will reach artificial super intelligence.

For each idea:
- Give me a hook line (<= 15 words, curiosity-driven)
- Outline the structure in 3 parts (hook, point, action)
- Include an example or analogy that will resonate with an audience of college graduates. 

Make them practical, non-generic, and designed to spark discussion.

To see how it works, just copy it and put it into your favorite large language model. I think you’ll be surprised and pleased with what results you obtain.

After the first pass, you can try this next:

Pick the best one and draft it.

You’ll get back a draft article about the model’s choice for the best among the 15 it first produced.

You can then steer the model using a prompt like this:

Tune the draft for the vc/tech founder voice. Also speculate that Google is most likely the winner.

It’s fun to see how the article evolves further with that voice and more speculation about the possible winner.

You can then ask the model to redraft it further:

Sketch two spicy counterarguments to the main thesis.

And so on. It’s fun to do a deep dive on a topic using this approach. The wide range of the first fifteen results narrows and deepens as you ask the model to refine the draft it has produced.

I’ve lost track of time exploring a topic of interest to me as I got back and forth with the model evolving my understanding. Some models will even assist you in that process by suggesting next steps along the way.

Let me know of your experiences using this kind of approach!