How To Thinking In Writing!

One of the best pieces I read so far this year.

Good thinking is about pushing past your current understanding and reaching the thought behind the thought. It often requires breaking old ideas. This is easier to do when the ideas are as rigid as they get on the page. In a fluid medium like thought or conversation, you can always go, “Well, I didn’t mean it like that” or rely on the fact that your short-term memory is too limited for you to notice the contradiction between what you are saying now and what you said 12 minutes ago.

When I write, I get to observe the transition from this fluid mode of thinking to the rigid. As I type, I’m often in a fluid mode—writing at the speed of thought. I feel confident about what I’m saying. But as soon as I stop, the thoughts solidify, rigid on the page, and, as I read what I’ve written, I see cracks spreading through my ideas. What seemed right in my head fell to pieces on the page.

Seeing your ideas crumble can be a frustrating experience, but it is the point if you are writing to think. You want it to break. It is in the cracks the light shines in.

When I write, I push myself to make definite positive claims. Ambiguity allows thought to remain fluid on the page, floating into a different meaning when put under pressure. This makes it harder to push your thinking deeper. By making clear and sharp claims, I reveal my understanding so that I—or the person I’m writing to—can see the state of my knowledge and direct their feedback to the point where it will help my thinking improve.

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Once I stretch my understanding thin in writing, I often see holes right away. I start correcting myself and discarding ideas already while typing. I cut ideas that are obviously flawed. I rewrite what feels ambiguous to make it more precise, concrete, unhedged, and true to my understanding.

The flaws I see immediately, however, are only the more superficial flaws. The deeper patterns take a longer time to emerge—because they are further from my established thoughts and so are harder to articulate.

Often, they occur first as subtle emotional cues. As I reread a passage, I notice a slight tension across my chest or my eyes fog over. For some reason, it doesn’t feel right. There is something wrong here. 

These subtle feelings are easy to dismiss (“Eh, words are slippery, I mean something slightly different . . . there is no reason to obsess about this”). But in my experience, it is these subtler problems that tend to open a path beyond my current understanding. I learned this from my wife, Johanna, who will often sit with a draft for several hours, not writing or editing, but simply articulating why something feels off to her. Our best essays have come out of the things she surfaced during those sessions.

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The emotional tone of these questions is, in my head, lovingly curious; I’m not trying to put myself down. I’m out to kill ideas. I want to help them evolve and spill forth more insight. Often this dialogue ends with me changing my mind about several premises and coming to a different conclusion, but the original idea remains the seed—no less valuable for having been proven wrong. It takes creativity and boldness to leap out and form a conclusion, and the part that criticizes must understand how dependent it is on the part that throws ideas at the wall. It is often easier to criticize than it is to synthesize a new position.

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Counterexamples are useful in two ways. Either you find a counterexample that a) proves one of the premises wrong but b) does not change your mind about the conclusion. Lakatos calls this a local (and non-global) counterexample. This means there is something wrong with your explanation. Perhaps you need to change that part of the explanation? Or perhaps you can simply drop it, making the mental model simpler and more general? Local counterexamples help you improve your explanation and get a better understanding.