Stuart_Armstrong comments on Infinite Certainty - Less Wrong
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If you say 99.9999% confidence, you're implying that you could make one million equally fraught statements, one after the other, and be wrong, on average, about once.
Excellent post overall, but that part seems weakest - we suffer from an unavailability problem, in that we can't just think up random statements with those properties. When I said I agreed 99.9999% with "P(P is never equal to 1)" it doesnt't mean that I feel I could produce such a list - just that I have a very high belief that such a list could exist.
An intermediate position would be to come up with a hundred equally fraught statements in a randomly chosen narrow area, and extrapoltate from that result.