How Paul Graham Actually Writes Essays

Paul Graham's essays look disarmingly simple: plain language, drifting structure, and then a line that suddenly clicks everything into place. Under the surface, though, he is following a very specific recipe: surprising question x exploratory drafting x brutal rewriting, all aimed at pieces that are "true, important, new, useful." Think of this less as a slogan and more as a workflow you can steal. As a writing coach, I'll walk you through that workflow in a way you can actually apply to your own drafts.

For a quick mental picture, imagine his process as three intertwined moves rather than separate stages. Surprising questions give the essay its energy, exploratory drafts generate unexpected ideas on the page, and brutal rewriting refines both the thinking and the sound of the sentences. Put differently: you collect what surprises you, ask one real question, write to discover what you think, then revise hard until your ideas and your prose finally match.

Step 1 - Collect your surprises and obsessions. Graham's best essays usually begin not from grand topics like "education" or "technology" but from little feelings that something is off: why school essays feel fake, why some programmers are wildly more productive, why certain kinds of work feels meaningful and others deadening. Your job is to treat those irritations and fascinations as raw material, jotting them into notebooks or files whenever they pop up. The more faithfully you collect these anomalies, the easier it becomes to spot questions that haven't already been answered to death.

Step 2 - Turn a topic into a question. Instead of thinking "I should write about school," you ask "Why does so much school writing feel dead?" or "What's actually going on when students fake essays?" In "The Age of the Essay," Graham sums this up by saying that an essay is something you write "to try to figure something out," not to dress up a conclusion you already have. Framing your piece as a question gives it direction without locking you into a pre-decided answer, which in turn makes it easier to stay honest when the draft surprises you.

Step 3 - Write a fast, bad version one. At this point you sit down and pour out a rough draft as quickly as you can, with zero expectation that it will be coherent or persuasive. In his short piece "Writing, Briefly," Graham describes spending more time on rewriting than on the initial pass, treating the first draft mainly as a way to drag half-formed thoughts into the open where he can see them. You should expect ill-fitting examples, shaky claims, and detours that go nowhere; the goal of version one is simply to get wet clay onto the table so you have something to shape.

Step 4 - Let the draft meander by interest. As you draft, you follow the most interesting thought from one paragraph to the next, even if it does not match the outline you imagined in your head. In his essays on the form, Graham argues that this kind of wandering is a feature of real inquiry: if you truly follow the question, the path will bend. When you hit a dead end, you back up and try a different branch, trusting that you can clean up the path later in revision.

Step 5 - Extract what's true, important, and new. Once that messy draft exists, you switch into treasure-hunt mode and start looking for the few parts that are actually worth keeping. Here it helps to keep three questions in front of you: what in here genuinely surprised me, what would a smart reader actually care about, and what could only you have written in this particular way. In "How to Write Usefully," Graham defines useful writing as telling people something "true and important" that they didn't already know, and says the job is to say it as unequivocally as possible. Those criteria are demanding, but they are also a powerful filter for trimming away fluff.

Step 6 - Rewrite in loops. This is the brutal part, and it is where most of the magic happens. On each pass you try to read your own prose as a skeptical, slightly impatient stranger, watching for two kinds of trouble: boredom, where your attention drifts, and friction, where your claims do not really convince you. Drawing on his essay "Putting Ideas into Words," Graham's view is that if a sentence sounds wrong in your ear, it usually means the thought underneath is still half-baked, so you fix the idea rather than just adding adjectives. A useful quick pass is: cut anything that bores you, rethink anything that feels fuzzy, and simplify any sentence you would be embarrassed to say out loud.

Part of this looping rewrite is making the language sound like an actual person. In "Write Like You Talk," Graham urges writers to "write in the same language you'd use if you were talking to a friend," on the grounds that this is both clearer and harder to fake. As a quick check, read a paragraph aloud and ask, "Would I really say this to someone I respect?" If not, you keep tightening until the sentences sound like a calm, thoughtful version of your real voice rather than a committee memo.

Step 7 - Use external readers as a reality check. At some point you have taken the draft as far as you can alone, and your private sense of what works stops being trustworthy. This is when you hand it to one or two smart friends and ask very specific questions: where did you get bored, where did you get lost, and which one sentence do you think I'll most regret later. Graham thanks readers on many of his essays and has described using them exactly this way, not to rubber-stamp his ideas but to locate blind spots he can no longer see. When two or more readers highlight the same weak spot, that almost always marks a real problem in either the idea or the explanation.

Step 8 - Do a final shaping pass. By now you know what the essay is really about, so you can prune the wandering path into something more direct while keeping the feeling of live thinking. Graham often keeps his digressions in the piece but moves them into footnotes, letting the main line of argument run cleanly from question to insight. On this pass you also watch for repetition, overly sharp lines you might regret, and side-ideas that deserve their own essays rather than a rushed paragraph here.

Step 9 - Publish and feed the loop. When he posts an essay on his site, Graham is not treating publication as the finish line; he is throwing the idea into the world to see what questions, objections, and misunderstandings come back. Over the years, those reactions have helped shape later essays and even startup-investing ideas, turning the whole archive into a record of thinking in public. For you, the venue might be a blog, newsletter, or shared document, but the principle is the same: once real readers engage, they generate the next round of surprises to toss back into your notebook.

Stepping back, most parts of this loop are strongly supported by what writing teachers and cognitive scientists know about how people think. Using writing to clarify thought, drafting quickly before your internal critic shuts you down, revising multiple times, and seeking feedback from real readers are all standard best practices, not just one hacker-investor's quirks. Treating essays as ways to figure things out rather than as performances to prove what you already know is also in line with research on learning by explanation: trying to teach someone else forces you to sharpen your own understanding.

The catch is that some of Graham's specific habits are tools to try, not commandments. Letting a draft meander freely works well if you are willing to cut ruthlessly later, but for newer writers it can turn into pages of unfocused wandering. Skipping any outline at all may suit him, yet many people benefit from a loose scaffold - a few anchor points or section headings - that they later feel free to rearrange. The right way to use this process is as a laboratory: adopt the moves that make your thinking sharper and discard the ones that consistently leave you stuck.

Here's what to avoid if you want to write in this spirit. Avoid starting from a thesis you feel you must defend at all costs; that makes you a lawyer, not an investigator, and it tempts you to ignore inconvenient evidence. Avoid writing to sound impressive rather than clear, a trap Graham warns about when he urges people to write as they talk. And avoid treating rewriting as cosmetic, tweaking only words and punctuation while leaving shaky ideas untouched, because in his system the whole point of revision is to rethink what you are saying, not just how you say it.

Knowing when to ask for help is part of the craft. If you have been through several rewrite loops and still cannot say what your essay is really about in one clear sentence, that is a sign you need a reader or a coach to ask blunt questions. If you keep avoiding your own draft because it feels boring or muddled, go back to your list of surprises and obsessions and see whether you chose a question that genuinely interests you. Outside eyes can help, but the process still starts with your own curiosity.

Bottom line, Paul Graham's method is a disciplined way to turn curiosity into useful essays: collect the anomalies that bother you, turn them into real questions, draft quickly to see what you actually think, revise in loops until ideas and sentences click, then publish and let readers feed you the next round of puzzles. Do that enough times and your essays stop being school-style performances and become tools for learning in public. In the process, you not only write better; you train yourself to notice more, think more clearly, and share what you find in a way that genuinely helps other people.