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Eugine_Nier comments on How can we get more and better LW contrarians? - Less Wrong Discussion
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I sometimes argue in favor of positions I don't really believe (i.e., assign p<.5 to) if I think the probability is higher than general consensus and I suspect at least Will Newsome frequently does the same.
Yes, but it's often a hassle. You risk being accused of trolling, overconfidence, &c., and it's difficult to claim that such accusations don't have some tinge of truth.
I suspect it's not overall a very good habit and that I bring it to LessWrong mostly because it happens to work well in my personal rationality practice. On LessWrong it's probably better to put in a little extra work to find a way to go meta—don't support a side, but show clear not-introspectively-obvious reasons why someone could hold a belief that was to them introspectively obvious and thus difficult to explain. I generally like the anti-democracy LW commenters because they seem to have practiced this skill.