OrphanWilde comments on Open thread, Feb. 01 - Feb. 07, 2016 - Less Wrong Discussion
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I'm not sure that's true. All the research I've seen on the subject suggests that successful people in most contexts harbor optimistic rather than accurate views of their chances, skills, and associates.
That said, there's probably a sweet spot.
Optimism changes your chances; changes the risks you will take, changes whether or not you'll employ your skills, changes how you interact with your associates.
Optimism changes your behaviour, that may or may not change your chances.
In any case, on the pessimism - optimism axis both extremes look like not a good place to be. To discuss where is the sweet spot in the middle you first need the ability (vocabulary and metrics) to talk about specific locations in the middle, otherwise it's all just handwaving.