What makes Paul Graham a great writer?

What makes Paul Graham a great writer?

In the last few months, I’ve heard these 4 statements from 4 different people:

  • “I wish I could write like Paul Graham.”
  • “If I had to pick one writer to imitate, it would be Paul Graham.”
  • “Paul Graham’s writing is the epitome of clarity.”
  • “Paul Graham inspired me to start writing.”

This widespread sentiment motivated me to dive deeper into Graham’s writing, with help from my collaborator & writing mentor Dr. William Jaworski. What’s Paul Graham doing that’s so special? In the world of writing, what do his fingerprints look like?

Here’s what we’ve observed.

He organizes each essay around a razor-sharp core idea.

All imagery in this blog post comes from the 1930 film The Blood of a Poet.

Every essay needs a core idea. Maybe you think of it as the focal point, the thesis, or the argument you’re making. Dr. Jaworski frames it as “a pithy one-liner that serves as an organizing principle for the whole essay.”

When you’re in tune with a core idea, writing feels easier. Intrusive thoughts soften and recede. You’re able to slow down and think more systematically. You start to see where your essay will end (and where a different one might begin—another day). You have a bullseye in your sights.

Usually, you can grasp the core idea of a Paul Graham essay by reading the title. My favorite examples are The Two Kinds of Moderate, The Bus Ticket Theory of Genius, and Write Like You Talk. As you read any of those, you’ll see how every paragraph, and in fact every sentence, connects with the core idea. His focus is sharp and unwavering.

Admire that commitment & focus, but realize that even for Graham, essay ideas aren’t sharp from the get-go. Don’t let hazy vision dissuade you: a blurry bullseye is better than no bullseye. The important thing is to not give up—and also to avoid falling in love with any particular idea.

…which brings me to a new point about Paul Graham’s writing!

He doesn’t fall in love with his ideas.

From experience, Paul Graham knows even smart people have bad ideas. That’s why it’s important not to get caught up in your own. Some of your ideas will be good; some won’t. That’s fine. In fact, it’s completely inevitable: if you want to have good ideas, you have to accept the reality of having bad ones.

In How to Write Usefully, Paul Graham states this principle about as point-blank as it gets:

If you write a bad sentence, you don’t publish it. You delete it and try again. Often you abandon whole branches of four or five paragraphs. Sometimes a whole essay. You can’t ensure that every idea you have is good, but you can ensure that every one you publish is, by simply not publishing the ones that aren’t.

Graham’s essay Startups in 13 Sentences is a subtler illustration of the same idea. There’s no fancy technical footwork—structurally, it’s a plain-Jane listicle. Yet, there’s real insight in it. There’s the feeling that these ideas have weight and presence. That’s because those 13 ideas have been curated from a wide range of options. The essay is not the product of 13 ideas; it’s the product of 1,000+ ideas, narrowed down to 13. Before that essay ever saw the light of day, Paul Graham sifted through many good, bad, and half-decent ideas, and selected the best.

When Paul Graham starts thinking, he often finds dead ends. He explores the twists & turns his thoughts can take, and eventually he finds the path down which he most wants to guide his readers. Choosing that path to the exclusion of the others requires being a ruthless self-editor—someone who can step back & observe his own writing from a healthy distance. This process is the mark of a good thinker, and it’s also a mark of a good writer.

He couples concepts with concrete examples.

About 70% of Paul Graham’s essays contain the word “example,” usually within the phrase “for example.” When he introduces an abstract idea, you’re never more than a sentence or two away from a well-picked example.

For example, in Copy What You Like, Graham writes, “It’s easy to be drawn into imitating flaws, because they’re easier to see, and of course easier to copy too.”

On its own, that sentence isn’t too useful. But immediately, Graham supplies a real example:

For example, most painters in the eighteenth and nineteenth centuries used brownish colors. They were imitating the great painters of the Renaissance, whose paintings by that time were brown with dirt. Those paintings have since been cleaned, revealing brilliant colors; their imitators are of course still brown.

Thanks to that follow-up, I have a better sense of what Graham means.

Graham uses lots of examples because he knows concepts are tools used for thinking about the world. But a tool is helpful only if you know how to use it, and you learn how to use a concept by applying it to real things.

Paul Graham’s examples show you how to apply concepts to real life. Applying unfamiliar concepts to familiar examples makes those concepts easier to master.

Here are three more short meta-examples:

From Being a Noob:

The more of a noob you are locally, the less of a noob you are globally. For example, if you stay in your home country, you’ll feel less of a noob than if you move to Farawavia, where everything works differently. And yet you’ll know more if you move.

From Stuff:

Nothing owns you like fragile stuff. For example, the “good china” so many households have, and whose defining quality is not so much that it’s fun to use, but that one must be especially careful not to break it.

From What Doesn’t Seem Like Work:

If something that seems like work to other people doesn’t seem like work to you, that’s something you’re well suited for. For example, a lot of programmers I know, including me, actually like debugging. It’s not something people tend to volunteer; one likes it the way one likes popping zits. But you may have to like debugging to like programming, considering the degree to which programming consists of it.

He creates rhythm by varying sentence length.

When people talk about a writer’s “voice,” they’re largely talking about the rhythm of the writing. Is it choppy? Is it droning? Does it feel conversational? Much of this comes down to the lengths of your sentences, and especially how you mix and match them.

Paul Graham rarely uses long sentences, but he mixes and matches short and medium-length sentences to create a rhythm that mirrors the pace of real conversation.

A well-placed short sentence creates a pause. The key expression here is well-placed: you wouldn’t want to listen to a speaker who follows every sentence with a dramatic pause. Paul Graham tends to taper the lengths of his sentences down until he reaches a key point—something he wants to emphasize. That’s where he pauses.

Here’s a perfect example from Life is Short. Notice how Paul Graham uses the two shortest sentences in the paragraph (bolded), nestled among longer ones, to create points of salience.

If life is short, we should expect its shortness to take us by surprise. And that is just what tends to happen. You take things for granted, and then they’re gone. You think you can always write that book, or climb that mountain, or whatever, and then you realize the window has closed. The saddest windows close when other people die. Their lives are short too. After my mother died, I wished I’d spent more time with her. I lived as if she’d always be there. And in her typical quiet way she encouraged that illusion. But an illusion it was. I think a lot of people make the same mistake I did.

During our review of Paul Graham’s writing, Dr. Jaworski identified this technique and explained it to me. As part of his explanation, he wrote this awesome paragraph that I can’t help but share:

“Imagine you and I are taking a leisurely stroll, conversing as we go—the pace of our words matching the pace of our strides. Then something happens. There’s something I want to say, but I have trouble saying it. It’s important. We slow down. We stop. I struggle to find the words. I utter them. One. By. One. For emphasis. See? I’m being waggish, of course, but I trust you see the point: when you want to emphasize something, you need to slow the reader’s pace with shorter sentences and bolder punctuation. Conversely, when you’ve covered what’s important, you need to regain momentum using longer sentences and lighter punctuation, and might even forgo full stops entirely in favor of commas, conjunctions, semi-colons, dashes, and other devices that keep the reader moving.”

For me, Dr. Jaworski’s illustration is the most intuitive way to understand this technique. Of course, that doesn’t mean I’ll master it overnight—it takes practice and patience. But now, I have an effective metaphor to guide me.

He doesn’t underestimate your intelligence.

Yes, Paul Graham prefers short sentences and short words—his essays pass the Hemingway test with flying colors. But that doesn’t mean he’s dumbing his writing down. Quite the opposite: Graham knows he’s talking about sophisticated ideas, so he presents them cleanly, getting his writing out of the way. He avoids over-explaining things, which is a great way to evade rabbit holes.

Basically, he knows how to put himself in a smart reader’s shoes, and as soon as he starts thinking, “Yep, I get it”—he stops.

He’s codified his own rules, and he follows them.

In 2005, Paul Graham codified his own rules for writing, and they’re exquisite. Get this: on my team of experienced writers, none of us had seen Graham’s rules before—but in our own separate ways, we’d each already learned to follow them.

So, straight from the horse’s mouth, here they are:

  • Write a bad version 1 as fast as you can; rewrite it over and over.
  • cut out everything unnecessary.
  • write in a conversational tone.
  • develop a nose for bad writing, so you can see and fix it in yours.
  • imitate writers you like.
  • if you can’t get started, tell someone what you plan to write about, then write down what you said.
  • expect 80% of the ideas in an essay to happen after you start writing it, and 50% of those you start with to be wrong.
  • be confident enough to cut.
  • have friends you trust read your stuff and tell you which bits are confusing or drag.
  • don’t (always) make detailed outlines.
  • mull ideas over for a few days before writing.
  • carry a small notebook or scrap paper with you.
  • start writing when you think of the first sentence; if a deadline forces you to start before that, just say the most important sentence first.
  • write about stuff you like.
  • don’t try to sound impressive.
  • don’t hesitate to change the topic on the fly.
  • use footnotes to contain digressions.
  • use anaphora to knit sentences together.
  • read your essays out loud to see (a) where you stumble over awkward phrases and (b) which bits are boring (the paragraphs you dread reading).
  • try to tell the reader something new and useful.
  • work in fairly big quanta of time.
  • when you restart, begin by rereading what you have so far.
  • when you finish, leave yourself something easy to start with.
  • accumulate notes for topics you plan to cover at the bottom of the file; don’t feel obliged to cover any of them.
  • write for a reader who won’t read the essay as carefully as you do, just as pop songs are designed to sound ok on crappy car radios.
  • if you say anything mistaken, fix it immediately.
  • ask friends which sentence you’ll regret most.
  • go back and tone down harsh remarks.
  • publish stuff online, because an audience makes you write more, and thus generate more ideas.
  • print out drafts instead of just looking at them on the screen.
  • use simple, germanic words.
  • learn to distinguish surprises from digressions.
  • learn to recognize the approach of an ending, and when one appears, grab it.

Room for improvement?

It’s hard to criticize Paul Graham as a writer. Actually, it feels heretical, which is why I think it’s important to do it.

I want to point out one thing that might stand between Paul Graham and an undying legacy as a great writer (if that’s a legacy he wants). That thing is risk aversion.

Paul Graham has refined his skill as an essayist to a point nearing perfection. But the peak he’s reached as an essayist might be a plateau in his overall development as a writer. It’s been a long time since Graham tried something new in his published writing.

In both of his latest pieces, Orthodox Privilege and The Four Quadrants of Conformism, I see an outstanding communicator whose surgical competence might be interfering with his intuition.  Don’t get me wrong: both essays are superb. In a sense, they’re flawless—almost the way auto-tuned music is flawless. There’s no imperfection, and that, in itself, might be a flaw.

What could Paul Graham do if he took more risks as a writer? I don’t know. He’s the creator; I’m just part of the peanut gallery. But given his great talent & skill, I hope he explores the possibilities.

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I’m happily indebted to both Dr. Jaworski and Pavel Brodsky for their essential contributions to this essay.

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