Notes on Paul Graham’s Writings About Writing

If you are someone looking for advice on writing, you rarely point to a computer geek turned entrepreneur for advice. In this essay, I take that plunge. Today, I want to discuss about Paul Graham. Prominently, his writing—and the advice he gives us on how we write and ought to write.

Paul is a prominent figure in the tech world. He is known for his startup accelerator firm, Y Combinator, which has successfully funded Airbnb and Reddit, among others. However, a lesser-known aspect of Paul is his essays. He writes on a wide range of topics: tech, philosophy, writing, and startup culture, to name a few. Even several entrepreneurs have come to think of his essays as essential for someone thinking about startups.

I came across Graham’s writings relatively late. When I read some of his essays, I found them intriguing. He is not merely thinking about thinking but advises everyone to think through writing. He says, in multiple essays, that writing makes one’s thinking clearer than when you first start out.

In this blog, I compile and try to make sense of Graham’s advice to writers (written through the early 2000s until recently). In reading all these essays, I have come to understand what it means to write an essay like Paul Graham’s (somewhat obscurely, if I may say so). To begin writing, one needs to read, and then through reading, one gets ideas. After having ideas, one needs to understand the writing process. Finally, one must know what makes for a good essay.

Paul Graham tells us to read first.

Many times, we all assume ourselves to be great writers. I, for one, try to think of myself as a somewhat okayish (to put it crudely) writer. That also comes from a certain inability to read enough and think broadly. I will work on this. So, Paul tells us that to be a good writer, you must read first. Read widely. Don’t hook yourself up to an audiobook. That is not reading. It is consuming information—like a robot.

Graham writes: “A good writer doesn’t just think, and then write down what he thought, as a sort of transcript. A good writer will always discover new things in the process of writing. And there is, as far as I know, no substitute for this kind of discovery.”

And to get good ideas, one needs first to read others—and then follow and understand how they write. Think of ways to figure out what and how others write. What works for them? What did you enjoy the most about this essay? All this helps. Therefore, one must read thoroughly and deeply to be able to think of things in the world.

Paul Graham on how to get good ideas.

Say you have read others—and followed how they write and what works for them. What next? You may be intrigued about what they are saying, how they are saying it, and if it makes any sense.

In another essay, Paul Graham tells us: “The way to get new ideas is to notice anomalies: what seems strange, or missing, or broken? You can see anomalies in everyday life (much of standup comedy is based on this), but the best place to look for them is at the frontiers of knowledge”.

Graham adds: “Knowledge grows fractally. From a distance, its edges look smooth, but when you learn enough to get close to one, you’ll notice it’s full of gaps. These gaps will seem obvious; it will seem inexplicable that no one has tried x or wondered about y.” Therefore, to be able to think of ideas is to think of anomalies in what you have read. Intrigue. That is the way out of being stuck. As students and academics, we are always stuck.

Paul Graham tells us to write as we speak.

Much of academics is all about jargon. I often used a lot of jargon. Therefore, guilty as charged. However, I am trying to improve here. Look at this essay itself, for example. Graham admits that he is not a good speaker. And that he uses a lot of “um” when he speaks. I am not sure about me. But all of us, consciously or unconsciously, end up using big words to convey simple things. Look at the texts of some subaltern scholars. They write in dense language that the subaltern is left out of its discourse and knowledge production.

Paul Graham says there is an interconnection between writing and speaking. In his 2015 article: “Write like you talk”, Graham writes: “Here’s a simple trick for getting more people to read what you write: write in spoken language”.

Writing well means making sure you interact with your audience. You speak to them like you speak with your friend. Graham writes: “If you want people to read and understand what you write, [you must learn to write like you speak to them]… Written language is more complex, which makes it more work to read. It’s also more formal and distant, allowing the reader’s attention to drift. But perhaps worst of all, the complex sentences and fancy words give you, the writer, the false impression that you’re saying more than you actually are.”

Sometimes, we want to use big words just to pretend when know stuff. It is easy. Throw a random word around, and act and feel cool. However, it is not easy to write when you speak. Speaking is informal, but writing is seen as formal. Graham notes: “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.” Therefore, he adds: “Before I publish a new essay, I read it out loud and fix everything that doesn’t sound like conversation. I even fix bits that are phonetically awkward; I don’t know if that’s necessary, but it doesn’t cost much.”

Therefore, if you just write like you speak, “you’ll be ahead of 95% of writers. And it’s easy to do: just don’t let a sentence through unless it’s the way you’d say it to a friend.”

Paul Graham tells us to write simply.

Writing simply just means using simple language, simple words, and simple sentences. Graham writes: “I try to write using ordinary words… [And] that kind of writing is easier to read, and the easier something is to read, the more deeply readers will engage with it.

I write academic journal articles. Barely anyone picks it up and reads it. But my blog—it circulates (unconsciously) across internet. Why? I don’t say deeply insightful stuff on my blog, but it still circulates, whereas an essay I would have written, say, for International Affairs, like this one, barely gets read. Simpler things are easier for people to relate to. They can learn through simpler things.

Anything complex is hard work. When you try to act smart (which you clearly aren’t if you use flowery language), a lot of readers (who, like myself, aren’t native English speakers) get lost. The more complex you write, the less you should expect others to read.

In his 2021 essay: ‘Write Simply’, Paul Graham writes: “Of course, fancy writing doesn’t just conceal ideas. It can also conceal the lack of them. That’s why some people write that way: to conceal the fact that they have nothing to say. Whereas writing simply keeps you honest. If you say nothing simply, it will be obvious to everyone, including you.” Therefore, Graham tells us, “The main reason I write simply is that it offends me not to”. If you write in complex ways, then you will definitely seem clumsy. He tells us that he writes the first draft and then spends days and hours editing it until he really feels confident about it. Much of the editing simply makes the essay simpler.

So, how does Paul Graham work on an essay?

Graham answers this question in his really old essay, published in 2005. Here it is:

This is a really good approach to all writings.

I tend to follow a few of these steps. I don’t usually gloss over my draft once I have written it. Most of the time, what I write the first time is what usually gets published. I spend time on each sentence to make sure it fits. But the point is to not just stick to something that doesn’t work for you so that it works for someone else. Be open to writing differently. It usually helps to know what works for you.

Now that we have gleaned through how Paul Graham writes, the last aspect of this essay is his opinion about what makes for a good essay. Let’s jump in.

Paul Graham discusses what makes for a good essay.

In today’s day and age, we work in tandem with artificial intelligence (AI). More often than not, the ChatGPT writes better than you. If so, why even try? I think if one were to treat writing as a vocation (something one ought to do), it would definitely make no sense. AI will do better than almost all the things we do now. And, with time, it will only get better. Therefore, it is important for writers to treat their writing as a way of telling something (new) that otherwise does not exist. Tell in ways an open AI cannot do. How do we do that?

Paul tells us that “good writing should be convincing, certainly, but it should be convincing because you got the right answers, not because you did a good job of arguing.” Unlike what we have been trained to peter out in schools and colleges, an essay is a beast of its own. An essay should not merely ask questions but also “has to come up with answers”. It should flow like a river, which sometimes hits against a wall but still flows. An essay should be interesting. How? Graham writes: “Interesting means surprise… [And] surprises are things that you not only didn’t know, but that contradicts things you thought you knew.” To be surprising, you have to be able to use yourself as a proxy for your reader. You should write about things you think of – and all that that comes off as surprising for you.

Graham adds: “If there’s one piece of advice I would give about writing essays, it would be: don’t do as you’re told. Don’t believe what you are supposed to. Don’t write the essay readers expect; one learns nothing from what one expects. And don’t write the way they taught you to in school”.

In his recent 2024 essay titled: ‘The Best Essay’, Paul Graham writes: “The best essay now would be one describing a great discovery we didn’t yet know about.” Writing essays is all about discovering ideas through writing. So, for that to happen, you have to find a “sufficiently puzzling” question. And then try to answer it. And not be afraid of cutting things out.

Paul writes: “One of the most dangerous temptations in writing (and in software and painting) is to keep something that isn’t right, just because it contains a few bits or costs you a lot of effort”.

Cover Photo by Pawel Czerwinski on Unsplash

Read other essays on writing here:

• On how novelist Orhan Pamuk writes.
• George Orwell’s six rules for writing.