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 realize that an easy way to cheat is to answer (0 (appropriate unit), 3^^^3 (appropriate unit))for questions 1-9, and answer (pi^e, pi^e) for question 10. That seems to be the "wrong" way to go about this task.
I wanted to deliver, to the best of my current knowledge (without looking anything up), 5% and 95% bounds for the true value, for each item. Where my knowledge was more limited, that meant a wider bound, but that shouldn't mean less effort to establish that bound, should it? That seems to be what you're implying.
Obviously, we need to learn that narrower ranges are not better, but if we want 90% ranges, we should work to ensure that the ranges are as close to 90% as our knowledge allows, not 99% just because we're reversing one kind of stupidity in order to achieve another.