The Best Essay | Paul Graham
The best essay would be on the most important topic you could tell people something surprising about.
Writing converts your ideas from vague to bad. But that's a step forward, because once you can see the brokenness, you can fix it.
The initial question you investigate matters, because you don't have an obsessive target in mind (it is precisely idea exploration that you want to do). This is to say: put care into what initial question you investigate when writing.
The most surprising new question being thrown off at this point is does it really matter what the initial question is? If the space of ideas is highly connected, it shouldn't, because you should be able to get from any question to the most valuable ones in a few hops. And we see evidence that it's highly connected in the way, for example, that people who are obsessed with some topic can turn any conversation toward it. But that only works if you know where you want to go, and you don't in an essay. That's the whole point. You don't want to be the obsessive conversationalist, or all your essays will be about the same thing.
How to have a good initial question then? To 1) “try to ensure what pops into your head is good” and 2) to be quick to cut.
I enjoyed the closing:
The most striking feature of this map of essay writing are the alternating stripes of inspiration and effort required. The questions depend on inspiration, but the answers can be got by sheer persistence. You don't have to get an answer right the first time, but there's no excuse for not getting it right eventually, because you can keep rewriting till you do. And this is not just a theoretical possibility. It's a pretty accurate description of the way I work. I'm rewriting as we speak.
But although I wish I could say that writing great essays depends mostly on effort, in the limit case it's inspiration that makes the difference. In the limit case, the questions are the harder thing to get. That pool has no bottom.
How to get more questions? That is the most important question of all.