Our hosts at Tricycle Developments have created PredictionBook.com, which lets you make predictions and then track your calibration - see whether things you assigned a 70% probability happen 7 times out of 10.
The major challenge with a tool like this is (a) coming up with good short-term predictions to track (b) maintaining your will to keep on tracking yourself even if the results are discouraging, as they probably will be.
I think the main motivation to actually use it, would be rationalists challenging each other to put a prediction on the record and track the results - I'm going to try to remember to do this the next time Michael Vassar says "X%" and I assign a different probability. (Vassar would have won quite a few points for his superior predictions of Singularity Summit 2009 attendance - I was pessimistic, Vassar was accurate.)
Fortunately, Dunning-Kruger does not seem to be universal (not that anyone who would understand or care about calibration would also be in the stupid-enough quartiles in the first place).
Again, I don't see why I couldn't. All I need is a good understanding of what I know, and then anytime I run into predictions on things I don't know about, I should be able to estimate my ignorance and adjust my predictions closer to 50% as appropriate. If I am mistaken, well, in some areas I will be underconfident and in some overconfident, and they balance out.
If there's a single thing mainly responsible for making people poor estimators of their numerical certainty (judged against reality), then you're probably right. For example, it makes sense for me to be overconfident in my pronouncements if I want people to listen to me, and there's little chance of me being caught in my overconfidence. This motivation is strong and universal. But I can learn to realize that I'm effectively lying (everyone does it, so maybe I should persist in most arenas), and report more honestly and accurately, if only to myself, after ... (read more)