SarahC comments on Doublethink (Choosing to be Biased) - Less Wrong
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I'm not sure. It's just that if it did I wouldn't go for it.
I know one person who's really well calibrated with probability, due to a lot of practice with poker and finance. When something actually is an x% probability, he actually internalizes it -- he really expects it to happen x% of the time. He's 80% likely to be right about something if he says he has an 80% confidence.
He doesn't seem too bad off. Busy and stressed, yes, but not particularly sad. Cheerful, even.