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Lumifer comments on Open Thread, Feb 8 - Feb 15, 2016 - Less Wrong Discussion
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Seems like a problem that could be solved by making more bets.
If you only make one bet, you have either 0% or 100% success rate, and neither reflects how good you actually are.
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.