Tag: writing advice

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Authors Writing

Write Till You Drop

An atmospheric evening scene shows a writer's desk lit by a warm lamp, featuring stacks of paper, books, and an empty coffee cup, while a large metal safe stands open nearby.

Annie Dillard died on Tuesday, September 15, at her home in South Wellfleet, Massachusetts. She was 81.

I have been reading her for years, and I keep returning to her because she makes writing feel both more serious and more alive. She was demanding without turning grim. She reminded you that the work is hard, then made you want to sit down and do it anyway.

Her essay “Write Till You Drop,” published in The New York Times in May 1989 and collected in The Writing Life, contains more useful advice about writing than many books on the subject. The line I remember first is this one: “You were made and set here to give voice to this, your own astonishment.” That seems to me the whole assignment. Pay attention to what stops you. Find the thing you cannot quite explain. Then try to give it a voice.

Dillard tells of a student asking a well-known writer, “Do you think I could be a writer?” The writer asks back, “Well, do you like sentences?” What a perfect answer. Writing begins there—not with wanting to be a writer, but with liking sentences enough to make them, take them apart, and make them again.

I have been blogging since 2001. Over that time I have written thousands of sentences, some better than others. The blog has been a way of noticing what I notice. It has also taught me that the only reliable way to keep writing is to write. Not to wait for a grand subject or a clear runway. Just begin with the thing at hand and see where the sentences lead.

Dillard is especially good on the danger of saving things. “Spend it all, shoot it, play it, lose it, all, right away, every time,” she writes. Do not hold back the best image, the sharpest thought, or the story you think belongs somewhere more important. Use it now. If you lock it away, she warns, you may open the safe later and find ashes.

That lands differently for me now. I recently started keeping a list of words and phrases I love, after reading that Susan Orlean has long done the same. I like the habit. It sharpens attention. But Dillard would probably lean over my shoulder and say: Good. Now spend them. A list is not the work. The words have to leave the safe.

The same is true of the book I am working on about Interstate 280. It is a long project, full of engineering, politics, landscape, memory, and side roads that keep turning into stories of their own. A smaller treatment might be easier. But Dillard has an answer for that, too: “It is no less difficult to write sentences in a recipe than sentences in Moby-Dick. So you might as well write Moby-Dick.”

She says a writer should play the edges of the field, like a tennis player who reaches for the shots that land at the lines. That feels right for the I-280 book. The highway is the center of the court, but much of the life is at the edges: a dam, a billboard that is not there, a ridge preserved from development, an engineer whose name has nearly disappeared. Those are the shots worth chasing.

Dillard closes with Michelangelo’s note to an apprentice: “Draw, Antonio, draw, Antonio, draw and do not waste time.” That is not complicated advice. Neither is her deeper promise: “No manipulation is possible in a work of art, but every miracle is.”

I keep a folder for the I-280 book. It is getting fat: a dam, a billboard that is not there anymore, a ridge somebody fought to preserve, an engineer whose name I have to look up every time. None of it is spent yet. Dillard would want to know what I am waiting for.

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.

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AI AI: Prompting Writing

AI as a Mirror, Not a Maker

I’ve been thinking a lot lately about how we move past the novelty phase of AI—beyond just asking a chatbot to “write a poem about a turkey” or summarize a meeting—and into actual thinking with these tools.

As a lifelong learner, I’m always on the hunt for workflows that help me synthesize information better. Most of the “AI for writing” advice I see online is pretty generic. But I recently came across a breakdown of how four high-profile writers are making effective use of tools like NotebookLM and Claude in ways that are much more sophisticated than simple text generation.

What jumped out at me is that none of these writers use AI to write for them. They use it to structure, challenge, and code.

Here are the four models that caught my eye.

1. The Triangulated Research Base (Steven Johnson)

Steven Johnson (Where Good Ideas Come From) has a workflow that solves a problem I face constantly: the messy “research phase.”

Instead of treating the AI as an oracle, he treats it as a connection engine. He creates a dedicated notebook (using Google’s NotebookLM) and uploads three distinct types of sources: a primary source (like a raw PDF or study), a secondary source (like a context article), and a multimedia transcript.

Then, rather than asking for a summary, he asks the AI to find the friction between them: “What themes appear in the interview transcript that contradict the historical account in the PDF?”

It’s less about getting an answer and more about finding the blind spots in your own reading.

2. The Diagnostic Editor (Kenny Kane)

This one really resonated with me because it mirrors the experiment I tried recently with my “Bubble Bath” post.

Kenny Kane uses Claude not to generate prose, but to act as a ruthless developmental editor. He uploads a messy draft and runs a “Diagnostic” prompt. He doesn’t ask “fix this,” he asks: “Where does the argument drift? Where does the energy drop?”

He even has the AI analyze his best writing to identify his specific “DNA” (sentence length, vocabulary choice) and then asks it to apply that same tone to his rougher sections. It’s using the AI as a mirror rather than a ghostwriter.

3. The Memo-to-Demo Shift (Dan Shipper)

Dan Shipper at Every is doing something fascinating that changes the definition of writing altogether. He argues that in the AI age, we shouldn’t just describe a concept; we should build a small app to demonstrate it.

If he’s writing about “Spaced Repetition,” he doesn’t just explain the theory. He asks Claude’s Artifacts feature to “Write a React component that lets a user test spaced repetition live in the browser,” and then embeds that little app directly into the essay. The writing becomes 50% prose and 50% software.

4. The Co-Intelligence Loop (Ethan Mollick)

Ethan Mollick focuses on breaking the echo chamber. Before he publishes, he spins up simulated personas—a skeptical VC, a confused novice, an expert in a tangential field—and asks them to critique his draft from their specific viewpoints.

It’s effectively a focus group of one.

How to Get Started

If you’re like me, seeing all these workflows might feel a bit overwhelming. My advice? Don’t try to overhaul your entire writing process overnight. Just pick one experiment to try this week.

Here are two simple entry points:

Experiment A: The “Blind Spot” Check (For Research)

If you are reading up on a topic, don’t just take notes. Open Google NotebookLM, create a new notebook, and upload your sources (PDFs, URLs, or pasted text). Then, ask this specific question:

“Based strictly on these sources, what is the strongest argument against my current thinking? What connection between Source A and Source B am I missing?”

Experiment B: The “Ruthless Editor” (For Writing)

If you have a rough draft sitting on your hard drive, copy it into Claude or ChatGPT and use this prompt (adapted from Kenny Kane’s workflow) before you do any manual editing:

“Act as a senior editor. Do not rewrite this text. Instead, analyze my draft and tell me: 1) Where does the argument lose energy? 2) Does the opening hook successfully promise what the conclusion delivers? Be critical.”

I’ve found that using the tools this way—as a partner for thinking rather than just generating—is where the real magic happens.

Which one will you try first?