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've resolved not to blame myself as much as I used to, I was young and not at all sure how to deal with the fact that my dad was dying. That and I didn't quite know he was dying, as my parents effectively told us lies of omission about his condition. That's part of what lead me to understand that there are real evils in this world, a realization which put me on track to being the best I can be...
Anyway, I know now that I was only quasi-rational then, and that this was partially the cause my mistakes. Mistakes which caused grief and wretchedness that I can sometimes hardly bare. I'm on track now though - never again.