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Most things I learn feel like they add to my knowledge base, but don't upgrade my thinking. The two things I've read that felt like they actually upgraded my thinking were the Lesswrong sequences, and Gödel, Escher, Bach. What are some things in that category for you?
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Checkout existential psychotherapy by Irvin d yalom... it’s TNG to Frenkle’s TOS. Unrelated; Out of Their minds is great biographical accounts of early CS pioneers.