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by softwaredoug 124 days ago
When I write book chapters I write, throw away, write, throw away. Mostly with no a-priori outline

But eventually I get to a point where all the failed attempts crystallize and it flows out of me start to finish in one sitting. Every piece of knowledge from those failed attempts crystallizes into one gestalt of how it’s supposed to be.

Those final “easy” 20 pages always come after 100 pages of discarded, frustrating, exploratory work that feels like it’s going nowhere.

Also a deadline helps.

2 comments

Yeah, one of the toughest but most rewarding lessons I've learned about writing is how valuable it can be to set aside your current draft and start from scratch.

It's very tempting to want to write an outline & then revise the outline until it's perfect, so that your first draft can be as solid as possible. That never works out well for me, though. It's only after I've written a substantial chunk of the thing that I realize half my ideas were bad and the other half are being poorly realized, and I start to understand the story I really want to write.

I'm very taken with this one HYTRADBOI talk [1] that applies a similar approach to software design. It's not something I've ever gotten a chance to apply, but it really appeals to me.

[1]: https://www.hytradboi.com/2025/03580e19-4646-4fba-91c3-17eab...

It was fun writing our book because I SAW you do that. And I had a different approach - I would outline obsessively and hold the whole chapter in my head at once before I started writing. Holding a whole chapter and cross referencing everything with everything else was O(N^2). You're approach for writing one instance of the chapter was linear O(N) but you did it M times... so O(M*N) ... maybe about the same :P