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).
Could you specify what you mean by "getting the transition started" or "crossing the first divide"? I'm surprised by the question.
In both my own history and the people around me (both people I know from rationalist communities, and people more representative of the broader American public), I tend to see fairly continuous gradations of rationalist skill and of rationalist disposition/goals, without an obvious "first step" to notice.
I think he's looking for a trigger we can activate in normal people. But I've read most of these stories and so far it seems the vast majority among us had a natural disposition for this ever since babydom. We could ask those who 'didn't have that disposition to give more details?