Lumifer comments on Open Thread, Feb 8 - Feb 15, 2016 - Less Wrong
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The problem is not finding out "how good you actually are". The problem is that making the bet locks you into a particular state of mind which involves more bias and less updating on evidence.
But still if you do a lot of small betting instead of few large there you have less chance to lock yourself in a hole.
It's not clear that this would be the case. Even if you're making only a few bets at a time (as opposed to participating in a liquid market), there will always be some odds at which you'll want to hedge the bet from the other side.