An excerpt from "The Age of the Essay," by Paul Graham

Surprise

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.

For example, in a recent essay I pointed out that because you can only judge computer programmers by working with them, no one knows who the best programmers are overall. I didn't realize this when I began that essay, and even now I find it kind of weird. That's what you're looking for.

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.

What should you think about? My guess is that it doesn't matter-- that anything can be interesting if you get deeply enough into it. One possible exception might be things that have deliberately had all the variation sucked out of them, like working in fast food. In retrospect, was there anything interesting about working at Baskin-Robbins? Well, it was interesting how important color was to the customers. Kids a certain age would point into the case and say that they wanted yellow. Did they want French Vanilla or Lemon? They would just look at you blankly. They wanted yellow. And then there was the mystery of why the perennial favorite Pralines 'n' Cream was so appealing. (I think now it was the salt.) And the difference in the way fathers and mothers bought ice cream for their kids: the fathers like benevolent kings bestowing largesse, the mothers harried, giving in to pressure. So, yes, there does seem to be some material even in fast food.

I didn't notice those things at the time, though. At sixteen I was about as observant as a lump of rock. I can see more now in the fragments of memory I preserve of that age than I could see at the time from having it all happening live, right in front of me.

Observation

So 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?

To some extent it's like learning history. When you first read history, it's just a whirl of names and dates. Nothing seems to stick. But the more you learn, the more hooks you have for new facts to stick onto-- which means you accumulate knowledge at what's colloquially called an exponential rate. Once you remember that Normans conquered England in 1066, it will catch your attention when you hear that other Normans conquered southern Italy at about the same time. Which will make you wonder about Normandy, and take note when a third book mentions that Normans were not, like most of what is now called France, tribes that flowed in as the Roman empire collapsed, but Vikings (norman = north man) who arrived four centuries later in 911. Which makes it easier to remember that Dublin was also established by Vikings in the 840s. Etc, etc squared.

Collecting surprises is a similar process. 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 find it especially useful to ask why about things that seem wrong. For example, why should there be a connection between humor and misfortune? Why do we find it funny when a character, even one we like, slips on a banana peel? There's a whole essay's worth of surprises there for sure.

If you want to notice things that seem wrong, you'll find a degree of skepticism helpful. I take it as an axiom that we're only achieving 1% of what we could. This helps counteract the rule that gets beaten into our heads as children: that things are the way they are because that is how things have to be. For example, everyone I've talked to while writing this essay felt the same about English classes-- that the whole process seemed pointless. But none of us had the balls at the time to hypothesize that it was, in fact, all a mistake. We all thought there was just something we weren't getting.

I have a hunch you want to pay attention not just to things that seem wrong, but things that seem wrong in a humorous way. I'm always pleased when I see someone laugh as they read a draft of an essay. But why should I be? I'm aiming for good ideas. Why should good ideas be funny? The connection may be surprise. Surprises make us laugh, and surprises are what one wants to deliver.

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.

People trying to be cool will find themselves at a disadvantage when collecting surprises. To be surprised is to be mistaken. And the essence of cool, as any fourteen year old could tell you, is nil admirari. When you're mistaken, don't dwell on it; just act like nothing's wrong and maybe no one will notice.

One of the keys to coolness is to avoid situations where inexperience may make you look foolish. If you want to find surprises you should do the opposite. Study lots of different things, because some of the most interesting surprises are unexpected connections between different fields. For example, jam, bacon, pickles, and cheese, which are among the most pleasing of foods, were all originally intended as methods of preservation. And so were books and paintings.

Whatever you study, include history-- but social and economic history, not political history. History seems to me so important that it's misleading to treat it as a mere field of study. Another way to describe it is all the data we have so far.

Among other things, studying history gives one confidence that there are good ideas waiting to be discovered right under our noses. Swords evolved during the Bronze Age out of daggers, which (like their flint predecessors) had a hilt separate from the blade. Because swords are longer the hilts kept breaking off. But it took five hundred years before someone thought of casting hilt and blade as one piece.

Disobedience

Above all, make a habit of paying attention to things you're not supposed to, either because they're "inappropriate," or not important, or not what you're supposed to be working on. If you're curious about something, trust your instincts. Follow the threads that attract your attention. If there's something you're really interested in, you'll find they have an uncanny way of leading back to it anyway, just as the conversation of people who are especially proud of something always tends to lead back to it.