Paul Graham Isn’t a Simple Writer, and Here Are Some of His Cool Tricks

Paul Graham’s writing often comes up in my coaching, especially with clients in the tech sector. He’s praised and envied by many. People wonder how he does it.

And, the other day, he wrote something that purports to give us his secrets. It’s a typically brisk, well-crafted post called Write Simply. Basically, the title says what it’s about. He advocates for simple, crisp language on the grounds that it’s digestible and timeless. This is reasonable. It’s advice I might benefit from following more often.

On the other hand. Lots of people already do what Paul Graham is advocating: write simply, put your ideas down, get in, get out. And they’re terrible. Their writing is weak and monotonous and soulless. It sounds like formulaic copy spit out by GPT-3 at the end of a long day.

So, why is Paul Graham better than other writers who try this transparent style?

Well, the thing about Paul Graham is that he’s actually not a simple writer. He’s complex and subtle. The complexity just isn’t at the level of vocabulary, so you don't notice it unless you look. It’s more about structure and flow—he has tons of little tricks that keep his writing ticking along.

I don’t know if he uses these tricks consciously. Part of being a good writer is learning a lot of micro-skills and then using them until they’ve become incorporated into your intuition, as John Salvatier would say. And some people are just natural rhetoricians.

But I do know that he’s well-equipped, and also that you can acquire some of his equipment. To demonstrate this, let’s break down some moments from one of my favorite PG posts, Haters.

Trick 1: Self-Riffing

One problem with a lot of informational, idea-based posts is that you don’t have to read them. There’s no added benefit from actually going from sentence to sentence. You can just scan the page, pick up a few salient facts, and continue with your day.

Paul Graham’s posts, on the other hand, are delicately constructed—they flow artfully from moment to moment. Following this flow is intrinsically pleasurable. You feel the arguments unfurling. Here’s an example.

Everyone's always going on about this singer, but she's no good! She's a fraud!

That word "fraud" is an important one. It's the spectral signature of a hater to regard the object of their hatred as a fraud.

See that? Instead of just moving to the next phase of the argument, he proceeds by referring to his own language. He puts a word in your head, and then calls your attention to it, then proceeds along the naturally generated trajectory. That makes the pivot from point to point buttery-smooth. It’s a nice tactic.

Perhaps “tactic” is actually a better label than “trick.” There’s no deception involved, after all. It’s just a graceful user experience.

Tactic 2: Occasional Fancy Language

In the post, PG does advocate using fancy language for effect. It’s not really emphasized, though. The essay isn’t called “write simply most of the time, and then don’t sometimes.” Fair enough—it’s arguable that using language for effect is a subtle trade, best pursued after mastering some basics. Maybe the best general advice is ‘take the 101 class.’

However, PG does use some really nice fancy language. For example, look at the passage we just examined!

That word "fraud" is an important one. It's the spectral signature of a hater to regard the object of their hatred as a fraud. They can't deny their fame. Indeed, their fame is if anything exaggerated in the hater's mind.

Spectral signature of a hater to regard, huh? That’s pretty slick. He could’ve just written ‘haters always think the objects of their hatred are frauds.’ Or ‘if somebody throws around the word fraud a lot, they’re probably a hater.’

But PG’s sentence is way better. The phrase “spectral signature” is gratifying. And it works because it’s so specific and poetic. It makes the hater sound like a person whose soul is polluted. Also, his use of such a specific phrase makes his judgement sound more emphatic. He dislikes haters enough that he’s saved some gleaming vocabulary just for them. Finally, the slightly unusual word order makes it an attention-grabber. When he deems the sentiment important, he uses brain-catching language.

You won’t find many such sentences in PG’s work. This is because he knows to deploy them occasionally. If you wrote like that steadily for ten paragraphs, it would sound pretentious and weird. But an occasional flash of eloquence rewards attention, evokes deeply, and endears you to the writer.

Tactic 3: Chattiness

There’s no one thing that makes prose good. However, here’s one frequent characteristic: great prose is often like a person talking, but impossibly perfectly. Good prose has the character of everyday speech, but elevated.

Anyway, here’s this nice bit:

What sort of people become haters? Can anyone become one? I'm not sure about this, but I've noticed some patterns. Haters are generally losers in a very specific sense: although they are occasionally talented, they have never achieved much. And indeed, anyone successful enough to have achieved significant fame would be unlikely to regard another famous person as a fraud on that account, because anyone famous knows how random fame is.

But haters are not always complete losers. They are not always the proverbial guy living in his mom's basement.

Couple of things to call out here. First: he doesn’t make up his mind about whether to use contractions or not. He uses “I’m” but also “they are.” This is a feature, not a bug. That’s what people sound like when they talk. Our speech conventions vary because we’re not robots.

Also, there’s some padding language. Not much, but it’s there. Check out “very specific.” People are often discouraged from using the word ‘very,’ because it's a mild intensifier that doesn't add much information. I disagree. ‘Very,’ used now and again, is a nice chatty emphasizer.

There’s also the double question, which sounds really talky. And “proverbial guy,” which is the kind of high/low diction you’d expect from an educated person in a comfortable mood.

This is simple language, but it’s a familiar, casual, almost slapdash simplicity.

And That Was Just One Chunk of One Post

There’s a lot more I could unearth here. PG is really good at a lot of things: delicate criticism, understated praise, pushing and pulling attention from line to line.

But I’m lazy. If you want to learn more, go study his writing yourself, or hire me. Anyway, I think I’ve made my point, which is that using simple language isn’t nearly enough. Writing decently is easy. But writing really well takes a lot of work—even, and perhaps especially, if you’re aiming at simplicity.