A bunch of years ago, when I was considering going to college, it was the middle of the whole dotcom thing. There were freelance sites springing up all over the place and I was trying to make money on them (and failing miserably, but so it goes.) One of the posts was the coding for an edutainment game in OpenGL, which seemed reasonably simple - it was more than I'd done before, but from their description and documentation it didn't sound like it should take even half as long as they were giving. And they were offering a few kilobucks for it, which, as a high schooler, is a hell of a lot of money.
So I wrote up a proposal and sent it in.
And, out of fifteen proposals, ended up in their 3 finalists for the contract.
And ended up 2nd overall.
I've always wondered what would have happened if I'd been 1st. I still think I could have done it, but it would have swung me into an entirely different area. I would have picked up that instead of college and possibly gone straight into the professional world. And while none of what I learned in college was what I was "supposed" to learn, I still learned a hell of a lot.
I can't even make educated guesses about what that would have done. It just diverges so fast - I can predict maybe a year after that event, at most, and then it swings into total chaos. So I will, of course, always be curious.
There's actually another moment. I applied to a total of nine colleges, and was accepted into three - UW, Oberlin, and CWRU. UW was local so I dropped that one immediately, but I really debated between Oberlin and CWRU. I was leaning more liberal arts, so I went to Oberlin, and maybe that was a mistake. Because it turned out that as much as I liked liberal arts I was really *bored* there. Most of the people I just didn't synch with. And I remember one thing that I noticed, and should have paid more attention to - while Oberlin had more females overall, CWRU's were, on average, a lot more interesting. So maybe I would have done better on the romance front.
On the other hand I was able to find enough people in Oberlin to be friends with (and a significant few that are absolute top-notch friends), but I always kind of suspected that I knew a much larger fraction of the people I really got along with than I'd have preferred. It's nice feeling like there are dozens of friendships waiting out there for you to run into, and thinking back on it, I didn't feel that way. Of course, I wouldn't give up the friends I have now . . . but also of course, if I'd gone to CWRU instead and was writing this about Oberlin, I'd probably say the same thing.
And maybe in CWRU I would have ended up staying in school, and who knows what that would have spiraled into.
So. I think those are the two biggest What If moments in my life.