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).
Every now and then I hear a story about (or meet in person) someone who not only left but managed to deconvert their whole family.
I wish, so dearly, that I could devote the time to at least seriously trying that...
I mostly just got lucky based on the circumstances. My little brother has fallen in with the 12 step program, though. It's working for him but it's nature is so anti-rationalist that it pains me somewhat. He started believing in God again; I threw some basic paradoxes at him and he just responded by saying he never really thought about it. I think he'll grow out of it eventually.
I went to Israel last year and was surprised and delighted to see that the country was positively European in its religious attitudes. Almost half of the people are non-believers, but I would be seriously afraid to try and deconvert any Orthodox practitioners, even or especially if they were family. They can get rather angry.