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Jayson_Virissimo comments on A Kick in the Rationals: What hurts you in your LessWrong Parts? - Less Wrong
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My choice example is dilettantes who learned from other dilettantes pontificating with supreme confidence about the subject matter they know little about (Hello, MWI!).
Oh, I got another one, mostly confined to this forum: people making up numbers for probabilities of certain events and feeling so much more Bayesian.
How are we supposed to get better at quantifying our degree of belief without practice?
You're not, which is why not keeping track of the results is a way of doing it wrong.
(Not that I do it, but then I don't assign spurious numbers to my feelings either. Possibly I should, but if I do then I need to keep track.)
I mostly approach this as a set of jargon words that express finer gradations of confidence than the conventional language.
That is, in normal speech I use tags like "I suspect that X," "I expect that X," "I'm fairly confident that X," "I doubt X", etc. On LW I use "I'm N confident that X" instead, where N is typically expressed to one significant figure (except I use ".99+" to denote virtual certainty).
I endorse that, although I also endorse remembering that what I'm talking about is my intuitions, not reality. That is, when I say I'm .7 confident that it's going to rain this afternoon, I have said something about my mind, not about rain.
I do find that the exercise of thinking more precisely about what my intuition actually is is helpful in encouraging me to pay more attention. That is, trying to decide whether I'm .6 or .8 confident in X (or whether all I can really say is that I'm .6-.8 confident) is a meaningful exercise in clarifying my own thoughts about X that I'm not as encouraged to do if my lexical habit is to say "probably X."
I do this in real life quite often. But I always try to explain that I'm talking about my state of mind. I occasionally get good reactions to this along the lines of whomever I'm talking to not having ever thought about the distinction between rain and what your mind thinks about rain.