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thomblake comments on Rationality quotes: May 2010 - Less Wrong
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This seems at odds with our notion of subjective probability, where we assume that significant lingering doubt after confidently assigning a 99%+ probability is evidence that your calibration is poor, and your estimate should have been lower.
Does the man really believe the voyage is, all things considered, a good one?
I'm not sure I understand what you mean when you say
The most confusing part about this is the part about poor calibration.
As for the rest, I don't deny that the fact that the man is unwilling to undertake the voyage is evidence that he doesn't think it is worthwhile, at least in ordinary contexts. But I think there is little to recommend the view that acting against your best reflective judgment is impossible or even extremely rare.