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Oligopsony comments on Litany of a Bright Dilettante - Less Wrong
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For any given assertion by an expert on a situation you are not an expert on, the probability that your criticism is correct is not small. However,
1) this does not mean that the expected value of the criticism is negative, even to the expert. If the expert receives 100 comments, 99 of which are confused and one of which blows apart their argument, then they are probably collectively valuable.
2) if the expert is unusually patient, your comment can present her with an opportunity to correct your confusion.
I would say that the important thing is more humility of presentation than humility of willingness to speak at all.
I agree, it's OK to ask what you think could be a stupid question. It's better than not asking, as you lose a chance to learn. It's not OK to insist that you are right and she is wrong once an explanation has been given, even if it does not make sense to you. Though, given the usual inferential distance problems, it's perfectly fine to ask for clarification.
From my experience, I think that your estimate of the odds of encountering a comment "which blows apart their argument" as about 1% is overly optimistic. Maybe in some other fields it's different. At best you can expect a minor correction or a qualification. If the expert is any good, they probably have heard it all before, and if they aren't, their ego would likely prevent them from admitting that they are wrong, anyway.
That's probably a more accurate way of phrasing things, yeah.