So you think its important to be able to estimate how well you are estimating something? Here is a fun test that has been given to plenty of other people.
I highly recommend you take the test before reading any more.
http://www.codinghorror.com/blog/2006/06/how-good-an-estimator-are-you.html
The discussion of this test at the blog it is quoted in is quite interesting, but I recommend you read it after taking the test. Similarly, one might anticipate there will be interesting discussion here on the test and whether it means what we want it to mean and so on.
My great apologies if this has been posted before. I did my bast with google trying to find any trace of this test, but if this has already been done, please let me know and ideally, let me know how I can remove my own duplicate post.
PS: The Southern California meetup 19 Dec 2010 was fantastic, thanks so much JenniferRM for setting it up. This post on my part is an indirect result of what we discussed and a fun game we played while we were there.
I got 8 right. The ones I got wrong were the Great Lakes (upper bound was too small by a factor of 1e8) and the currency in circulation (my range was .75-1.25T, and the right answer was slightly lower than my lower bound).
The problem I have with this is while it's structured well to punish overconfidence, it's not structured well to publish underconfidence. You can do better than 95% of respondents (according to the graph the author posted) if you write down -inf for your lower bound and +inf for your upper bound, since all 10 will be within your range (and so your error magnitude is 1, just as if you got 8 right). The fact that you're twice as bad at estimating as someone who writes down 0 as a lower bound and +inf as a upper bound shows up nowhere.
The best test of estimation ability would probably be: each guess costs you log(upper)-log(lower), and a guess that includes the answer gives you Y points. Y determines the minimum level of knowledge you need to guess, but if you narrow your guess you improve your score. You could then figure out what confidence interval people are using from the width they select, and see how that compares with their reported confidence.
This comment reflects how I realized I could game this... AFTER I took it though. Guess -inf to +inf for 9 of them, and something quite tight for the 10th. Then you've got your 90%.... but you don't really.