wedrifid comments on Rationality Quotes August 2013 - Less Wrong
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I think it's good to be well-calibrated.
It is usually best to be socially confident while making well-calibrated predictions of success. The two are only slightly related and Downey is definitely talking about the social kind of confidence.
Good point. I'm still not sure I like his framing of social interactions as getting people on "your" team (which I may be partly biased in by the source of the quote), but the objection in my initial post isn't a good one.