Paul Graham has an essay on “The Age of Essays.” Here’s an excerpt:
So what’s interesting? For me, interesting means surprise. Interfaces, as Geoffrey James has said, should follow the principle of least astonishment. A button that looks like it will make a machine stop should make it stop, not speed up. Essays should do the opposite. Essays should aim for maximum surprise.
I was afraid of flying for a long time and could only travel vicariously. When friends came back from faraway places, it wasn’t just out of politeness that I asked what they saw. I really wanted to know. And I found the best way to get information out of them was to ask what surprised them. How was the place different from what they expected? This is an extremely useful question. You can ask it of the most unobservant people, and it will extract information they didn’t even know they were recording.
Surprises are things that you not only didn’t know, but that contradict things you thought you knew. And so they’re the most valuable sort of fact you can get. They’re like a food that’s not merely healthy, but counteracts the unhealthy effects of things you’ve already eaten.
How do you find surprises? Well, therein lies half the work of essay writing. (The other half is expressing yourself well.) The trick is to use yourself as a proxy for the reader. You should only write about things you’ve thought about a lot. And anything you come across that surprises you, who’ve thought about the topic a lot, will probably surprise most readers.
So if you want to write essays, you need two ingredients: a few topics you’ve thought about a lot, and some ability to ferret out the unexpected.
The ability to ferret out the unexpected must not merely be an inborn one. It must be something you can learn. How do you learn it?
The more anomalies you’ve seen, the more easily you’ll notice new ones. Which means, oddly enough, that as you grow older, life should become more and more surprising. When I was a kid, I used to think adults had it all figured out. I had it backwards. Kids are the ones who have it all figured out. They’re just mistaken.
When it comes to surprises, the rich get richer. But (as with wealth) there may be habits of mind that will help the process along. It’s good to have a habit of asking questions, especially questions beginning with Why. But not in the random way that three year olds ask why. There are an infinite number of questions. How do you find the fruitful ones?
I write down things that surprise me in notebooks. I never actually get around to reading them and using what I’ve written, but I do tend to reproduce the same thoughts later. So the main value of notebooks may be what writing things down leaves in your head.