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There’s fast system 1 and slow system 2 thinking. There’s also very slow system 3 thinking where you doubt the assumptions you’re making. From my poker/chess experience it’s usually a mistake to overthink in this manner…you’ll end up doing something you rejected earlier

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There is fast system 2 thinking that masquerades as system 1 thinking and everyone thinks people who do that are “calculating”, which is technically correct, but hurtful