Paul Graham is one of my favorite essayists. The following are some excerpts from his excellent 2004 essay, “The Age of the Essay“.
The most obvious difference between real essays and the things one has to write in school is that real essays are not exclusively about English literature. Certainly schools should teach students how to write. But due to a series of historical accidents the teaching of writing has gotten mixed together with the study of literature. And so all over the country students are writing not about how a baseball team with a small budget might compete with the Yankees, or the role of color in fashion, or what constitutes a good dessert, but about symbolism in Dickens.
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 the late 19th century the teaching of writing was inherited by English professors. This had two drawbacks: (a) an expert on literature need not himself be a good writer, any more than an art historian has to be a good painter, and (b) the subject of writing now tends to be literature, since that’s what the professor is interested in.
…
The other big difference between a real essay and the things they make you write in school is that a real essay doesn’t take a position and then defend it.
…
Defending a position may be a necessary evil in a legal dispute, but it’s not the best way to get at the truth, as I think lawyers would be the first to admit. It’s not just that you miss subtleties this way. The real problem is that you can’t change the question.
And yet this principle is built into the very structure of the things they teach you to write in high school. The topic sentence is your thesis, chosen in advance, the supporting paragraphs the blows you strike in the conflict, and the conclusion– uh, what is the conclusion? I was never sure about that in high school. It seemed as if we were just supposed to restate what we said in the first paragraph, but in different enough words that no one could tell.
…
To understand what a real essay is, we have to reach back into history again, though this time not so far. To Michel de Montaigne, who in 1580 published a book of what he called “essais.” He was doing something quite different from what lawyers do, and the difference is embodied in the name. Essayer is the French verb meaning “to try” and an essai is an attempt. An essay is something you write to try to figure something out.
Figure out what? You don’t know yet.
…
If all you want to do is figure things out, why do you need to write anything, though? Why not just sit and think? Well, there precisely is Montaigne’s great discovery. Expressing ideas helps to form them.
…
Questions aren’t enough. An essay has to come up with answers. They don’t always, of course. Sometimes you start with a promising question and get nowhere…An essay you publish ought to tell the reader something he didn’t already know.
…
An essay is supposed to be a search for truth. It would be suspicious if it didn’t meander.
The Meander (aka Menderes) is a river in Turkey. As you might expect, it winds all over the place. But it doesn’t do this out of frivolity. The path it has discovered is the most economical route to the sea.
The river’s algorithm is simple. At each step, flow down. For the essayist this translates to: flow interesting. Of all the places to go next, choose the most interesting.
…
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 found the best way to get information … 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.
…
[T]he 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.
…
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.
…
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.
…
Gradualness is very powerful. And that power can be used for constructive purposes too: just as you can trick yourself into looking like a freak, you can trick yourself into creating something so grand that you would never have dared to plan such a thing. Indeed, this is just how most good software gets created.
…
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’re 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.
…
Popular magazines made the period between the spread of literacy and the arrival of TV the golden age of the short story. The Web may well make this the golden age of the essay. And that’s certainly not something I realized when I started writing this.