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It's often mistakenly believed that medieval universities were mostly seminaries. In fact they were more law schools. And at least in our tradition lawyers are advocates, trained to take either side of an argument and make as good a case for it as they can. Whether cause or effect, this spirit pervaded early universities. The study of rhetoric, the art of arguing persuasively, was a third of the undergraduate curriculum. [5] And after the lecture the most common form of discussion was the disputation. This is at least nominally preserved in our present-day thesis defense: most people treat the words thesis and dissertation as interchangeable, but originally, at least, a thesis was a position one took and the dissertation was the argument by which one defended 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. Why bother? But when you understand the origins of this sort of "essay," you can see where the conclusion comes from. It's the concluding remarks to the jury.

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. When I give a draft of an essay to friends, there are two things I want to know: which parts bore them, and which seem unconvincing. The boring bits can usually be fixed by cutting. But I don't try to fix the unconvincing bits by arguing more cleverly. I need to talk the matter over.

At the very least I must have explained something badly. In that case, in the course of the conversation I'll be forced to come up a with a clearer explanation, which I can just incorporate in the essay. More often than not I have to change what I was saying as well. But the aim is never to be convincing per se. As the reader gets smarter, convincing and true become identical, so if I can convince smart readers I must be near the truth.

The sort of writing that attempts to persuade may be a valid (or at least inevitable) form, but it's historically inaccurate to call it an essay. An essay is something else.

Trying

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. And so you can't begin with a thesis, because you don't have one, and may never have one. An essay doesn't begin with a statement, but with a question. In a real essay, you don't take a position and defend it. You notice a door that's ajar, and you open it and walk in to see what's inside.

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. Indeed, helps is far too weak a word. Most of what ends up in my essays I only thought of when I sat down to write them. That's why I write them.

In the things you write in school you are, in theory, merely explaining yourself to the reader. In a real essay you're writing for yourself. You're thinking out loud.

But not quite. Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well. So it does matter to have an audience. The things I've written just for myself are no good. They tend to peter out. When I run into difficulties, I find I conclude with a few vague questions and then drift off to get a cup of tea.

Many published essays peter out in the same way. Particularly the sort written by the staff writers of newsmagazines. Outside writers tend to supply editorials of the defend-a-position variety, which make a beeline toward a rousing (and foreordained) conclusion. But the staff writers feel obliged to write something "balanced." Since they're writing for a popular magazine, they start with the most radioactively controversial questions, from which-- because they're writing for a popular magazine-- they then proceed to recoil in terror. Abortion, for or against? This group says one thing. That group says another. One thing is certain: the question is a complex one. (But don't get mad at us. We didn't draw any conclusions.)

The River

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. But those you don't publish. Those are like experiments that get inconclusive results. An essay you publish ought to tell the reader something he didn't already know.

But what you tell him doesn't matter, so long as it's interesting. I'm sometimes accused of meandering. In defend-a-position writing that would be a flaw. There you're not concerned with truth. You already know where you're going, and you want to go straight there, blustering through obstacles, and hand-waving your way across swampy ground. But that's not what you're trying to do in an essay. 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. [6]

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. One can't have quite as little foresight as a river. I always know generally what I want to write about. But not the specific conclusions I want to reach; from paragraph to paragraph I let the ideas take their course.

This doesn't always work. Sometimes, like a river, one runs up against a wall. Then I do the same thing the river does: backtrack. At one point in this essay I found that after following a certain thread I ran out of ideas. I had to go back seven paragraphs and start over in another direction.

Fundamentally an essay is a train of thought-- but a cleaned-up train of thought, as dialogue is cleaned-up conversation. Real thought, like real conversation, is full of false starts. It would be exhausting to read. You need to cut and fill to emphasize the central thread, like an illustrator inking over a pencil drawing. But don't change so much that you lose the spontaneity of the original.

Err on the side of the river. An essay is not a reference work. It's not something you read looking for a specific answer, and feel cheated if you don't find it. I'd much rather read an essay that went off in an unexpected but interesting direction than one that plodded dutifully along a prescribed course.

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.