I'm sympathetic to everything you say.
In my experience there's an issue of Less Wrongers being unusually emotionally damaged (e.g. relative to academics) and this gives rise to a lot of problems in the community. But I don't think that the emotional damage primarily comes from the weird stuff that you see on Less Wrong. What one sees is them having born the brunt of the phenomenon that I described here disproportionately relative to other smart people, often because they're unusually creative and have been marginalized by conformist norms
Quite frankly, I find the norms in academia very creepy: I've seen a lot of people develop serious mental health problems in connection with their experiences in academia. It's hard to see it from the inside: I was disturbed by what I saw, but I didn't realize that math academia is actually functioning as a cult, based on retrospective impressions, and in fact by implicit consensus of the best mathematicians of the world (I can give references if you'd like) .
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That sounds like you engage in binary thinking and don't value shades of grey of uncertainty enough. You feel to need to judge arguments for whether they are true or aren't and don't have mental categories for "might be true, or might not be true".
Jonah makes strong claims for which he doesn't provide evidence. He's clear about the fact that he hasn't provided the necessary evidence.
Given that you pattern match to "crackpot" instead of putting Jonah in the mental category where you don't know whether what Jonah says is right or wrong. If you start to put a lot of claims into the "I don't know"-pile you don't constantly pop between belief and non-belief. Popping back and forth means that the size of your updates when presented new evidence are too large.
Being able to say "I don't know" is part of genuine skepticism.
I'm not talking about back and forth between true and false, but between two explanations. You can have a multimodal probability distribution and two distant modes are about equally probable, and when you update, sometimes one is larger and sometimes the other. Of course one doesn't need to choose a point estimate (maximum a posteriori), the distribution itself should ideally be believed in its entirety. But just as you can't see the rabbit-duck as simultaneously 50% rabbit and 50% duck, one sometimes switches between different explanations, similarly to an MCMC sampling procedure.
I don't want to argue this too much because it's largely a preference of style and culture. I think the discussions are very repetitive and it's an illusion that there is much to be learned by spending so much time thinking meta.
Anyway, I evaporate from the site for now.