Doug_S. comments on Expected Creative Surprises
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anon: The short definition of "well-calibrated" is that if things you assign X% probability to actually do happen X% of the time, you are well-calibrated. If you go around saying that you are 90% certain of your answers on an exam, and you get a 90, you are well-calibrated. If you say that you are 90% certain and you get a 50, you are not well-calibrated.
For the long version, see A Technical Explanation of Technical Explanation". (Highly recommended!)