To break up the awkward silence at the start of a recent Overcoming Bias meetup, I asked everyone present to tell their rationalist origin story - a key event or fact that played a role in their first beginning to aspire to rationality. This worked surprisingly well (and I would recommend it for future meetups).
I think I've already told enough of my own origin story on Overcoming Bias: how I was digging in my parents' yard as a kid and found a tarnished silver amulet inscribed with Bayes's Theorem, and how I wore it to bed that night and dreamed of a woman in white, holding an ancient leather-bound book called Judgment Under Uncertainty: Heuristics and Biases (eds. D. Kahneman, P. Slovic, and A. Tversky, 1982)... but there's no need to go into that again.
So, seriously... how did you originally go down that road?
Added: For some odd reason, many of the commenters here seem to have had a single experience in common - namely, at some point, encountering Overcoming Bias... But I'm especially interested in what it takes to get the transition started - crossing the first divide. This would be very valuable knowledge if it can be generalized. If that did happen at OB, please try to specify what was the crucial "Aha!" insight (down to the specific post if possible).
I went to a very good Catholic elementary school, one run primarily by priests trained by Jesuits. The priests commonly visited classes, and anything could be interrupted to have an impromptu theological or philosophical discussion. The classes encouraged questioning and doubt in all areas of study. We actually read philosophers such as Plato, Descartes, and Aquinas in the later years.
While I doubt that every child who went through this experience with me came out an ardent seeker of truth, I nonetheless believe this had a huge impact on who I'd become. Also, I should note that I've heard most Catholic schools aren't this awesome.
Did I really say "Dominicans"? I meant "Jesuits", of course.
It's been a while.