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ChristianKl comments on Rationalist fiction: a Slice of Life IN HELL - Less Wrong
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I don't think that teaching people to expect worse case scenarios increases rational thinking.
Not expecting them, but anticipating them. Anticipating how things can go wrong, and pre-empting that. Like Harry buying that medikit. Although it turned out to be useless, because he hadn't been prepared to do what it took to keep his friends safe.
It's more rational to make expected utility calculations than trying to cover yourself against every worse case scenario that you can imagine.
See pre-mortem.