Writing tools I learned from Paul Graham

I started reading Paul Graham because I was interested in startups. But I continued reading him because I became interested in writing. Similarly, he once told an interviewer: “You have got me as your guy for programming and entrepreneurship or something like that. And, actually, probably, it is writing. More than anything else.”1 

It was hard to figure out why his writing works: I’ve never seen anything simpler. The words making up his essays, if written separately on index cards, can be understood by beginner English learners, giving an impression of shallowness. Constructed into sentences and paragraphs, they’re one of the richest. How does he do it?

Like all great writers, Graham uses form to serve content. Here are my observations. 

Labeling it 

Think about our affinity for naming: we can’t help but give anything a name because, otherwise, it doesn’t exist. Naming makes things memorable and recallable: in coding you give a function a simple name so you can call it afterward. Ditto for writing. 

Graham likes to label concepts. This makes it easy to revisit them in his essay: instead of reiterating an explanation, all he has to do is write one or more words. Labeling also ties the ideas presented in his essay, making it all the more memorable. 

Here’s an example from Earnestness

Jessica and I have certain words that have special significance when we're talking about startups. The highest compliment we can pay to founders is to describe them as ‘earnest.’

Another term Graham used is Fastidiousness about truth—from How to Think for Yourself:

Fastidiousness about truth means more than just not believing things that are false. It means being careful about degree of belief.

Later in this essay, he refers to Fastidiousness about truth more than once. It would have been harder to recall the earlier passage if he hadn’t labeled it: 

Without this fastidiousness about truth, you can't be truly independent-minded. It's not enough just to have resistance to being told what to think.

And again: 

Can you increase your fastidiousness about truth? I would think so. In my experience, merely thinking about something you're fastidious about causes that fastidiousness to grow.

From How to Write Usefully—keep in mind that he expanded on these terms before grouping them in the following sentence: 

I believe the formula I've given you, importance + novelty + correctness + strength, is the recipe for a good essay.

As for readers, they’ll associate the special connotations, arguments, and feelings you mentioned earlier with the correlating label you created. And you can invoke it wherever without the fear of losing meaning. 

Unexpected comparisons

Few writers make comparisons in nonfiction writing. They introduce new concepts and immediately build on them, expecting the reader to have a reference at hand. Or, slightly better but worse still, they explain unfamiliar concepts without invoking similar, more popular ones. 

In almost all of Graham’s writings, he explains a novel concept by tying it to a basic example—one that can be understood by all. Here’s Graham in The Bus Ticket Theory of Genius explaining why some people have an obsession with something: 

There are people who collect old bus tickets. Like many collectors, they have an obsessive interest in the minutiae of what they collect. They can keep track of distinctions between different types of bus tickets that would be hard for the rest of us to remember. Because we don't care enough. What's the point of spending so much time thinking about old bus tickets?

Another from How to Write Usefully where he compares thinking well and qualification to, wait for it, the accelerator and clutch: 

These two counterbalance each other, like the accelerator and clutch in a car with a manual transmission. As you try to refine the expression of an idea, you adjust the qualification accordingly. Something you're sure of, you can state baldly with no qualification at all, as I did the four components of useful writing. Whereas points that seem dubious have to be held at arm's length with perhapses.

And it doesn’t have to be a whole paragraph. Here’s an example from Write Like You Talk:

Informal language is the athletic clothing of ideas.

This tool works best if you’re writing to the public or anyone who has vested interest in what you do but lacks subject command. In essence specialized knowledge adheres to the same first principles, so it should be easy to think of something relevant. 

Wrong assumptions 

In Paul Graham’s essays, including false assumptions, conventional beliefs, and how things go wrong is as important as the truth. You learn as much from how things don’t work as how they do, if not more. 

I find this to be an effective way of convincing others: instead of starting by why x works, you list first all the reasons conventional truths y and z don’t. Here’s a passage from the classic Do Things That Don’t Scale

There are two reasons founders resist going out and recruiting users individually. One is a combination of shyness and laziness. They'd rather sit at home writing code than go out and talk to a bunch of strangers and probably be rejected by most of them. But for a startup to succeed, at least one founder (usually the CEO) will have to spend a lot of time on sales and marketing.

The other reason founders ignore this path is that the absolute numbers seem so small at first. This can't be how the big, famous startups got started, they think. The mistake they make is to underestimate the power of compound growth.

Then you write the facts: 

You'll be doing different things when you're acquiring users a thousand at a time, and growth has to slow down eventually. But if the market exists you can usually start by recruiting users manually and then gradually switch to less manual methods.

Humans are instinctively more attentive to warnings. To capture readers’ attention, tell them first what to avoid. 

Asking questions

Here’s a tool Graham uses so often that it’s hard to consider accidental: he starts a paragraph with a question. Examples are ample: 

Is there a way to cultivate curiosity? To start with, you want to avoid situations that suppress it.

How can you ensure that the things you say are true and novel and important? Believe it or not, there is a trick for doing this.

What can one do in the face of such uncertainty? One solution is to hedge your bets, which in this case means to follow the obviously promising paths instead of your own private obsessions.

Questions increase clarity: if you ask a pointed question in your essay, there’s no choice but to answer it. It also helps with flow: if you’re stuck, thinking about questions relevant to your topic opens new doors.   

The way to make it integrated within your writing is to ask the right question: what would the reader want you to answer at this moment? In the last quote, Graham asked how we could face uncertainty. It was a natural progression of his essay: he wrote earlier that choosing a novel interest to pursue might carry the risk of wasting time. 

Assuming POV

Actions are caused by actors. If you’re writing about the former, you’ll need to probe the latter. 

A striking feature of Graham’s writing is his ability to assume an actor’s point of view, accurately describing their motivations. Here’s an example from Why Nerds are Unpopular

But I think the main reason other kids persecute nerds is that it's part of the mechanism of popularity. Popularity is only partially about individual attractiveness. It's much more about alliances. To become more popular, you need to be constantly doing things that bring you close to other popular people, and nothing brings people closer than a common enemy.

It’s fair to suggest that Graham wasn’t a bully, but he was able to describe the motivation of becoming one. 

Another from Do Things that Don’t Scale

But perhaps the biggest thing preventing founders from realizing how attentive they could be to their users is that they've never experienced such attention themselves. Their standards for customer service have been set by the companies they've been customers of, which are mostly big ones. Tim Cook doesn't send you a hand-written note after you buy a laptop.

So how do you reach this level of perspective? I think it happens after thinking deeply about the subject. If you direct your attention towards uncovering others’ motivations, you’ll come up with something.

Writing like God 

“How do you write a leader?” a recruit at The Economist asked. “Pretend you are God,” a senior editor replied. 

Graham’s style emits similar confidence. At times, his sentences feel more like a commandment than an opinion. Graham explains how he does it in How to Write Usefully

… 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.

Here are four sentences from different essays of his. Notice the tone in each: 

I know the politicians are mistaken because it was my job to predict which people will become billionaires.

Why can't there be people interested in self-driving cars or social networks for their own sake? When you look at the question from this side, it seems obvious there would be.

You don't want to start a startup to do something that everyone agrees is a good idea, or there will already be other companies doing it.

With the result that writing is made to seem boring and pointless. Who cares about symbolism in Dickens? Dickens himself would be more interested in an essay about color or baseball.

In being confident, you’re doing your reader a favor. Essentially, we read to look for answers, to lessen our sense of ambiguity. You don’t have to be sure of everything you write, of course. But it helps to be sure of something to build on.

Providing a manual

Graham’s essays are filled with valuable, applicable takes. This is not a unique tool in itself: if there’s one thing all essay writers should aim for, it’s adding value. Rather, it’s the delivery that sets him apart: he clearly states the problem and the solution. 

In Write Like You Talk, Graham plainly acknowledges the difficulty of doing like the title says (problem), then tells you what to do about it (solution): 

It seems to be hard for most people to write in spoken language. So perhaps the best solution is to write your first draft the way you usually would, then afterward look at each sentence and ask "Is this the way I'd say this if I were talking to a friend?" If it isn't, imagine what you would say, and use that instead. After a while this filter will start to operate as you write. When you write something you wouldn't say, you'll hear the clank as it hits the page.

Another from How to Start a Startup—he cautions that socializing in school doesn’t work for hackers if they want to start a startup (problem), advising them instead to start their own projects (solution): 

Don't make a conscious effort to schmooze; that doesn't work well with hackers. What you should do in college is work on your own projects. Hackers should do this even if they don't plan to start startups, because it's the only real way to learn how to program.

These tools aren’t only for essays: they work in any setting, suit every medium, and can be communicated through all languages. I started what I thought would be a quick study on how Paul Graham writes. Actually it’s about how he thinks.


From Interview with the Masters by Robert Greene.