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 only had 5 correct even though I knew about the involved bias from several sources and had done the (more extensive) test on http://www.projectionpoint.com/test1.php some time ago.
My main problem was the sheer scale of some problems, like the volume of the Great Lakes, which screwed up all the calculations in my head. Also, I did actually kinda-know a few of these items, but misremembered them and overconfidently didn't adjust my margins for safety.
Still, hitting a target with over 10 orders of magnitude in range isn't exactly accuracy.