Powerful tools for thought usually arise as a byproduct of real work in a field rather than "I have an idea for a tool!" (Hindu-Arabic numerals, microscopes, RenderMan, Mathematica). => People interested in tools must get into a context s.t. real work incites tool-work. Not easy!
Conversation
I wonder if you’ve considered seeing it from a different angle: improving students’ tools instead of teachers’ tools.
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Spent many years trying! Now I don't find the student/teacher dichotomy very interesting—but I do think the low-/high-investment/skill augmentation dichotomy is really meaningful.
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The angle I was thinking about is, what if anyone with enough intrinsic motivation / skin in the game had better tools to learn. In a way, you don’t have the fit problem anymore, because fit is the starting point?
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Ah, yes, that's a good framing for much of my recent focus. But the fit problem I'm highlighting isn't about the authenticity of the user's contexts—it's about the power necessary in the *inventor's* context!
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If you switched the frame to the student, wouldn’t a good inventor be an effective student themselves? Someone who would understand the limits of their current studying methods and wanted to augment them?
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Possibly, yes, for the case of inventing tools for students, if the needs of the inventor's studying generalize to others' needs!

