Who: Paul Graham

Claim To Fame: Paul Graham is a computer scientist, startup investor, and essayist. He is known for his work on the programming language Lisp, for co-founding Viaweb (which eventually became Yahoo! Store), and for co-founding the Y Combinator seed capital firm. In 2001, he started publishing essays on paulgraham.com, which now gets around 15 million page views per year. Paul is also the author of On Lisp, ANSI Common Lisp, and Hackers & Painters.

Where To Find Paul: His Website, Amazon, Twitter

Praise For Paul: “Graham’s essays…are not only timeless…but an incisive and edifying tutorial in entrepreneurship, responsibility, and leadership.” — Ryan Holiday, bestselling author of Stillness Is The Key, The Obstacle Is The Way, and The Daily Stoic

Along with your books and blog, you are an investor and entrepreneur. When during the day do you write? Do you have a slotted time each day or is it more when you could find the time?

At the moment writing is the main thing I do. I write between dropping my sons off at school in the morning and picking them up in the afternoon. I can sometimes write in the evenings too, but if I get 5 hours in, I’m happy.

Where do you like to write? What does your ideal work environment look like?

All I really need is a quiet room with a door that closes and at least one window. But the ideal office would be a cabin in the woods with lots of bookshelves, a sofa long enough to lie down on, and a desk heavy enough that it didn’t wobble.

Do you have any pre-writing rituals or habits before you sit down to write?

Ideally not. Ideally I already have the next few sentences lined up in my head, and I just sit down and start writing. But unfortunately that only happens about 20% of the time. When it doesn’t, I’m in trouble, because I do things like check Twitter, which is not good for the brain. You’d think by 55 I’d be more organized, but apparently not.

What do you do when the writing isn’t coming easy? Do you struggle at all with that dreaded enemy of writing: writer’s block?

I get small-scale writer’s block in the sense that it sometimes takes me a couple hours to figure out what to write next, but I don’t get it on a larger scale than that. I’ve never had a period of weeks or months where I couldn’t write.

Maybe if I wrote stories this would be more of a problem, but writing essays is basically thinking out loud.

The way I figure out what to write next is to walk. Sometimes it’s enough to pace around my office, but sometimes I have to go out and go for a walk.

How do you know if something you’re working on is not worth publishing or not any good? Have you developed any criteria that lets you evaluate your own work?

I have a trick for this. I think the goal of an essay is to surprise the reader. And if you write about a topic you understand fairly well and you’re able to discover things you didn’t consciously realize when you started writing, they’ll probably surprise most readers too. That’s the test: am I surprising myself?

But I do have a fail-safe. I get friends to read drafts of most essays, and sometimes they find major problems. I’ve killed at least two whole essays because friends didn’t like them.

Writers have to be master prioritizers — juggling all sorts of projects and deadlines at the same time. That’s certainly the case for you. Do you have any methods for managing tasks and time so to not let overwhelm sneak in?

I don’t have any other projects at the moment actually, and I haven’t had deadlines since grad school. My m.o. has always been to write whenever there wasn’t something else I had to do. That’s still my m.o., but now it means I can just write through most days.

It was harder to write essays when I was running Y Combinator, but not impossible. YC doesn’t have a 9-5 kind of office. I’d go there when I had meetings, but otherwise I was at home, and when I was at home I could write.

Are there any traits you think great entrepreneurs and great writers have in common?

They notice anomalies that other people skip over.

Great writers tend to be voracious readers. What does your reading habit look like?

To be honest, I read mostly at bedtime. It seems lazy to be reading a book during the day. Before I had kids I used to, but now when the boys are in school I feel like I ought to be working. Sometimes I’ll take a book with me to a cafe and read, but this is conscious self-indulgence, like the cake I’m eating with it.

The book I’m reading at bedtime is The Odyssey of all things. E. V. Rieu’s translation. A deeply pleasing book. I read some translation when I was younger, but I didn’t know enough history to appreciate it.

The edition is no small part of the pleasure: a wonderful Penguin Classic published in 1946. The paper is so soft that the book falls open in your hand.

What books or writers have most influenced the way you think and the way you write?

Wodehouse, above all, is my model for good writing, but I like a lot of 20th century British writers. They wrote so straightforwardly.

When I think of who has influenced the way I think, though, it’s not writers but mathematicians and scientists and engineers. Hardy’s Mathematician’s Apology for example, or Hamming’s “You and Your Research.”

What is your advice to aspiring writers?

Write! You have to practice to get better. If you can’t do anything else, write in a journal.

That’s pretty standard advice. But this bit might not be: become a connoisseur of bad writing. When you read something that seems bad, try to figure out why. Is it because the author is being dishonest? Is the rhythm off? Is the diction too formal? How would you say it? Once you’re good at noticing mistakes, it becomes harder to produce them.

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