Senthil comments on We Change Our Minds Less Often Than We Think - Less Wrong
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Aren't people consistently underconfident when it comes to their money? Everybody does something, invest in something, but aren't really sure about it even after they've done it. It's in its most extreme when it comes to the stock market.
Another instance is when people approach members of the opposite sex who they think are attractive. They consistently misunderestimate themselves.
Otherwise it depends on what their used to, like people in technology are underconfident when it comes to negotiation and so forth.