On re-reading this: http://www.paulgraham.com/essay.html, I decided that I liked it so much that I'd try to make a summary. If you haven't read the original, go read the original. It's beautifully written. I'm suspicious of beautiful writing because you can end up believing things that aren't true if they're well expressed. So I'm trying to pick out the thread of the argument and some handy maxims for essay-writing.
School essays were dull.
Because they're about English Literature, and that's dull.
Even Dickens wouldn't be interested in an essay about symbolism in Dickens.
Why did we do them?
After the Dark Ages, people rediscovered the classics.
The Greeks and Romans knew much more than the Europeans of the 12th century.
Relearning their stuff was really important.
Study of ancient texts was most of what scholars did.
This period lasted perhaps 200 years.
But the study of ancient texts was considered the highest pursuit for 500 more.
Universities used to teach writing.
Until teachers were required to do research. What should the teachers research?
If it's worth studying old texts, it must be worth studying modern ones too.
So writing teachers have to be researchers into modern literature as well.
They end up teaching writing about modern literature.
Schools imitate universities.
The end product is that schoolkids write essays about modern literature.
This is an imitation of an imitation of a thing that's 500 years out of date.
School essays take a position and defend it.
That's also a fossilized idea.
The structure comes from medieval law schools.
Good writing should be convincing, but it should be convincing because you got the right answers, not because you did a good job of arguing.
If you write something unconvincing, talk it through with the person who finds it unconvincing. You may come up with a clearer way of saying it, but more often you'll find that you have to change what you're saying. If you can convince clever people, then you're probably near the truth.
In 1580, Michel de Montaigne published a book of essais, or "tries".
An essay is something you write to try to figure something out.
You don't know what it is yet, so you can't begin with a thesis.
You begin with a question.
Montaigne's great discovery is that writing ideas down helps to form them.
In a real essay, you're writing for yourself. Thinking out loud.
But having an audience makes a difference. It forces you to think well.
You don't always come up with answers. Don't publish those.
Anything interesting will do.
The Meander is a river.
Meandering is not a flaw in a search for the truth.
At each step, go in the most interesting direction.
Backtrack if you get stuck.
Clean up your train of thought, but not so much that you lose spontaneity.
Err on the side of the river
Interesting is the same thing as surprising.
How was it different to what you were expecting? is a good question.
Surprises are things that contradict things that you thought you knew.
How do you find surprises?
Only write about things you've thought about a lot.
Then things that surprise you will also surprise readers.
So you need things that you've thought about a lot, and the ability to ferret out the unexpected.
What should you think about?
Anything can be interesting, even working in fast food.
The author sees more things in his memories of being sixteen than he saw at the time.
So the ability to ferret out the unexpected must be learnable.
Consider history. The more you learn, the more connections you can make.
Collecting surprises is similar. Life gets more surprising as you get older.
Perhaps there are ways to speed the process up.
Ask why? about things that seem wrong.
Scepticism is helpful in this.
Pay attention to things that seem wrong in a humorous way. Humour is a sign of surprise.
Write down things that surprise you in notebooks. It's not necessary to read them, though.
Being cool is an impediment. Dwell on your mistakes.
Seek out situations where inexperience will make you look foolish.
Study lots of different things. Include history. History is 'all the data we have so far'.
History gives us confidence that there are many good ideas under our noses.
Above all, pay attention to things you're not supposed to. If you're curious, trust your instincts. Follow the threads that attract your attention.
Once, only a tiny number of writers could publish essays.
Now everyone can.
The web may make this the golden age of the essay.
And that's not something I realized when I started writing this.