Tag: storytelling

Categories
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
Cuba Photography Street Photography

Havana, In Deep

Dangling Conversation - Havana - 2013

There is a box between them with a screen in it, and to this day I do not know what it is for. It could be for sifting. It could be for rolling. It sat on the table in that Havana market like a piece of furniture too tired to explain itself, and the man rested his forearm on it the way men rest their forearms on things that have been useful to them for a long time, without needing to look at it. A couple of guys a few steps off were selling meat, and somewhere a radio was losing a slow fight with distance.

He was asking her something. You could see it before you could hear it, if you could have heard it at all, which I could not, standing twenty feet away with a camera and no Spanish worth the name. His eyebrows were doing the work. His mouth was doing the work. The cigarette in the corner of his lips had gone unlit and forgotten, a prop in a scene that had moved past needing it.

She had not expected the question. That was the whole of it, the thing the photograph is actually about. Above and behind them the light came down through warehouse glass gone frosted with age, softened, the hard edges sanded off. It had been falling on that table for years before either of them sat down at it. A woman’s face has a setting it returns to between thoughts, and hers had been somewhere else — the work, the heat, the cigarette she’d just lit, which she now held between two fingers like a held breath, smoke rising into that same light, catching it, going from invisible to visible to invisible again. Then he spoke, and the setting changed. Her eyes came around to him sideways, the way eyes do when the rest of the head hasn’t decided yet whether to follow. Caught. Not afraid — caught, the way you’re caught remembering something mid-sentence, or caught by a question that arrives at an angle you didn’t see coming.

They had stepped away from whatever the work was — the particular slackness of people on a break, elbows down, shoulders forward, the posture of two people who have stopped doing the thing they get paid to do and have not yet decided to start talking about anything in particular, except that he just had.

Neither of them knew I was there, and I have never quite settled how I feel about that. I took something from two people who never agreed to give it. I have made my peace with it the way photographers do, which is imperfectly, but I have not stopped thinking about it. This is the only kind of photograph worth making all the same, the kind where you are not in the room, not really, where the camera has gone as invisible as the screen on that box, recording a question and an answer that the two of them will forget by the end of the day and that I will keep for the rest of my life, lit by a window neither of them ever turned around to notice.

What they were talking about, I will never know. I have looked at this photograph for thirteen years now and I still want to know.

Categories
Business Storytelling

The Closed Laptop

The conference rooms all look the same after a while. Same long table. Same chairs that cost more than they should. Same window with the same view of the same parking lot baking in the same California sun. You stop seeing them. You develop a kind of practiced receptivity, a professional openness that is also, if you are honest, a professional distance. You have heard the story before. You know where you are in the presentation without looking at the slide number.

Until the day someone sits down across from you and closes their laptop and says: can I just tell you our story?

Fred Wilson, the venture capitalist at Union Square Ventures, has spent forty years learning to tell the difference between founders who can build and founders who can make you believe. The skill he overweights now, he’ll tell you plainly, isn’t technical. It’s selling. Recruiting, fundraising, convincing customers, inspiring teams. “Actually being able to write code,” he said recently, “is probably not a big deal anymore.” What matters is whether you can cross the distance between your vision and someone else’s imagination and deposit something true and alive on the other side.

Most founders never figure this out. They build the deck instead. They pull the projector cable from the drawer — there is always a drawer, there is always a cable — and the room fills with blue light and bullet points and the comfortable geometry of a prepared presentation, and what never happens is the thing that needed to happen.

But there was this one morning.

He came in with his cofounder in the flat gray light that Silicon Valley gets in February, when the rain has stopped but the sky hasn’t decided what it wants to be. They were early. He set his bag down and sat directly across from me — not at the presenter’s angle, not with one eye already calculating the distance to the screen — directly across, the way you sit with someone you already know, or intend to. Neither of them reached for the cable in the drawer.

He looked at me with the particular steadiness of a person who has decided not to manage the moment.

Can I just tell you our story?

I want to be honest about what happened next, which is that I felt something shift before he said another word. Not a decision exactly. More like the precondition for a decision, the ground tilting slightly in a direction I hadn’t chosen. I was, in some way I couldn’t have defended rationally at the time, already with him. And I knew it, and I knew it was not an entirely reasonable response to a man who had been in the room for less than a minute, and I felt it anyway.

The laptop stayed closed for the next twenty minutes. No transitions. No bullet points. No hockey stick arcing toward a number reverse-engineered from a desired outcome. Just his voice and what he believed and the quality of attention you give a person when there is nothing else in the room to look at.

The deck came later. It was beautiful. By then it didn’t need to be anything except true.

Storytelling is not a skill in the way that financial modeling is a skill. It is older than that by such a margin that the comparison almost doesn’t make sense. What we are really talking about is the oldest technology human beings possess — a person in a room, a voice, an image made of nothing but words and the willingness to believe in them. It was doing its work around fires forty thousand years before the first conference room was built, and it has never once required a projector.

What the great storytellers understand, and what the best founders understand in the same unspoken way, is that a story is not a transfer of information. It is a transfer of inner states. When it works — when it really works — something that existed inside one person gets reconstructed inside another, and the listener emerges changed. Not persuaded. Not informed. Changed. These are different experiences, and only one of them makes a person willing to bet their career on something that doesn’t exist yet.

The deck puts glass between the teller and that possibility. The founder stands at the edge of the blue light pointing at things, and the room evaluates the things, and what never happens is the transfer. Everyone files out having formed opinions about the slides rather than beliefs about the person. Opinions and beliefs are not the same.

Wilson understands this even if he wouldn’t use these words. When he says the skill is selling, what he means underneath the selling is: can this person walk into a room and make other people inhabit their vision? Not convince them. Inhabit. The difference is the difference between reading about a place and being there. One of them changes how you act. The other one you forget on the drive home.

The projector cable is still in the drawer. Someone will pull it out next week, and the room will fill with blue light, and another founder will stand at the edge of it pointing at things, hoping that the right font and the right graph will do the work that only a human being, exposed and without props, can actually do.

It won’t. It never does.

The CEO who closed his laptop had been carrying a story he believed in, and he knew the story was the thing, not the packaging around it. He understood that the oldest container is also the most powerful one. His own voice. A room. Someone willing to listen.

I was ready to work with him before he said another word.

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)