I want to write better essays. I have written five or six good ones, but often I fail to meet my standard. Let me reason through what marks the essays that turned out well, to see if I can better judge if new ideas will measure up. So here are some things that seem true for my best essays and which I sometimes fail to do in my less good essays:

1. Good essays are, for me, born from rich experience or deep knowledge.

   1. The anti-pattern I fall prey to is: oh, this is an interesting new area, let’s do some research and write!

2. An insight, or a series of insights, arises from that experience.

   1. Antipattern: I fall in love with a story, and then I try to extract insights out of it. Or I have a shallow insight and start fleshing it out. Or I set out boldly with a question I would be excited to answer but don’t know if I can.

3. As I contemplate the insight, I surface stories, case studies, and other richly detailed stuff that gives depth, nuance, complexity, and richness to the thinking.

4. As I sketch the idea out, moving pieces and stories around, a clear unity springs forth. Often a core framing, a question, a concept, or a tight narrative structure. (The Alice anecdote in Looking for Alice, the overarching question in Childhoods of exceptional people.)

5. I find, connected to the core idea, a sentence or a story that can act as a bold opening. Something that establishes a tone and a rhythm.

Something like that, in this order, is the algorithm behind the essays that I end up most proud of. I think the place where I get lost most often is around 2. - I fail to notice insights in areas where I have rich experience. Sometimes I’m too restless at stage 3, though that is less of a problem - it just creates problems during writing.

How do you recognize that an idea will turn into a good essay?