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I’d think the iterative approach should work (start with stuff that already exists, then look out for itches + build capacity to build tools). Itch == idea + at least one user/context of use (you)
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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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At the moment, I'm using it to study cognitive psychology and design, and to help me learn about my own research concepts. As far as teach—nothing's felt compelling enough yet. It's a problem for my current work that I'm not that intrinsically excited by teaching/explaining.
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I see this through a genealogical perspective: if someone is interested in computing as a new medium, ask them how they got there. It it's to unfrustrate themselves because they need something to do what they couldn't do => good sign.