If you read this far you might actually want to read my story: Borrowed one of these 'popular misconception' books from my grandfather who was slightly into conspiracy stuff and revisionism, esp. in regards to Russian/German WW2 plans. Was super surprised that some really basic ideas of the book completely failed to be understood by anyone I talked to about. Had the same with some minor content of my first lecture on Economy. Read a lot, got weird hobbies, did PR work for some, got surprised by disinterest and/or hostility toward them. Systematized, that its not a property of topic X, but of the person I talk to and my presentation. Got a somewhat reasonable opinion on many many many topics, found out that libertarianism leads to many of those by easier reasoning. Became an atheist. Read the common know Feynman books somewhat before. (actually had those recommended to me by a physicist, who is a member of a little known religion from the 1844s). Discussed with atheists, learned some rationality stuff. Found OB, read OB. Got a rationalist girlfriend that pointed out the flaws in OB/LW writings, learned to some degree to understand that. Had my brain hacked by someone who claims rationality, and shares many many ideas with me, but got important things very wrong. Left that group, left libertarianism and basically ran out of political labels. Read Harry potter and laughed a lot.
Not all in this order.
The hook point on OB was 'that alien message' which I found over reddit, and tried to understand by reading it three times over a few days. Then I went all awwww and since then I basically read stuff and try to implement it.
The first hookpoint into reasoned thinking seems to have been the lexicon. (They became quite popular here. Its a bit like myth busters without the stunts, and in writing.) But I was already really curious before. Being the youngest of three brothers with a age gap of 6,7 might have created a runaway optimization pressure, because for years I was always the one knowing least. That has changed by now. Same for having bright older friends. What also helped was doing different things with/in different groups of people, and having a inhomogeneous circle of friends. Both age and occupation wise. Its odd how many people seem to know only folks their own age, doing basically the same thing. Sadly no one I learned from took anything from me. And also there was no one to recommend GEB to me at any point. The book is 2 years older than me! My curiosity to understand things lead me pretty far, and I value it much. But there is still a long way to go to WIN
... a member of a little known religion from the 1844s ...
This is a pretty well-informed crowd. You don't need to explain what a libertarian is, you don't need to explain who Feynman was, and most people will know what you are talking about if you mention Bahai. And those who don't know how to use wikipedia.
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).