I really enjoyed this writeup by Holden Karnofsky on what it feels like to work on fuzzy, hard-to-articulate research / investigation work, and what his process for doing that looks like, with a real example from the very early days of GiveWell:
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I love that Holden included that level of detail in his example. That makes it way more useful as a tacit knowledge case study:
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A genre that I wish existed and doesn't seem to: "tacit knowledge case studies"
An important part of acquiring tacit knowledge in e.g. management, software design, etc. seems to be getting lots of training data—trying out a lot of ideas, seeing which ones go well/poorly + why.
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Interestingly, I think I'm much better at working on wicked problems now, and use a number of the same strategies Holden does, e.g. writing things down (cold-takes.com/learning-by-wr) and vegetating while subconsciously working on a problem (in my case, I take walks).
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Really glad to know that I'm not the only one who lets these problems simmer while doing something completely mindless.
Someone walks into my office, sees me pacing frantically.
Them: "What are you doing?"
Me: "Working!"
Look, I swear that skimming a Wikipedia page about the climate of the Falkland Islands is helping me formulate this thing I want to say. Honest!
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