Surprise as Epistemic Target
Surprise is the target of good essays and a useful guide in intellectual work generally.
Surprises = things you didn't know + things that contradict what you thought you knew. These are the most valuable facts: they update prior beliefs rather than merely adding to them. They counteract the unhealthy effects of prior knowledge (the tendency to see only what confirms the model you already have).
Using yourself as a proxy
Write about topics you've thought about a lot. Anything that still surprises you — someone who has put in real time — will probably surprise most readers. The bar is correct because it's self-calibrating: shallow surprises that anyone would notice aren't interesting; only things that persist after real engagement are worth pursuing.
Graham's example: while writing about great hackers, he noticed you can only judge programmers by working with them, so no one actually knows who the best ones are. He didn't realize this when he began. That's the kind of thing he was looking for.
How to cultivate surprise-finding
- Ask why about things that seem wrong. Not random why-questions (like a 3-year-old), but targeted at things that seem off: why is this norm this way? Why doesn't this bother people?
- Skepticism: assume things are achieving 1% of what they could. Counteracts "things are the way they are because they have to be."
- Pay attention to the inappropriate, unimportant, or unassigned. If curious, trust the instinct. Follow the thread.
- Study lots of different things — unexpected connections appear across domains (jam, bacon, pickles, and cheese: all preservation techniques; same pattern shows up in how books and paintings age).
- Include history — especially social and economic, not just political. It's all the data we have so far.
The sword example: swords evolved from daggers, with a separate hilt attached. As swords got longer, hilts broke. It took 500 years before anyone thought to cast the hilt and blade as one piece. That's the kind of thing that only registers as surprising if you're in the habit of asking why.
Two ingredients for essays
- A few topics you've thought about deeply
- The ability to ferret out the unexpected within them
The first can be cultivated by going deep on anything. The second is a learnable habit of attention.
Related: essay-as-exploration (surprise-finding is the goal of exploration), meander-principle (surprise is what you're flowing toward at each step), humans-are-not-automatically-strategic (the general principle that valuable epistemic habits must be practiced deliberately)