The earliest one I can remember was - seriously now - catching a long over-the-shoulder Nerf football pass, at night, on my street, in very poor street lighting, against kids four or five years older than me. I remember what a big deal they made about the catch - it was as if I just won the Superbowl. I might have been 8 or 9 years old. I got such confidence from that.
Of course, I crapped my pants following a bunch of those same kids around on one of their paper routes, on my bike, and despite the obvious smell, denied it. I was actually surprised when I got home and found crap in my underwear. Kinda weird.
Around that time, I was goaded in to a foot race against a very fast 5th grader. I was in 3rd grade I think, and always took the blue ribbon in the 50 yard dash at field day. I still remember his name - Tim Kruse. It was a dead heat. We did it again - dead heat. The bell rang, he shook my hand (didn't say a word), and back to class we went. I think that's when I learned that it's only frightening to challenge yourself if you let it.
In 6th grade, myself and one other guy (Mike Nevins) had both perfect attendance and perfect grades. In 4th grade, he and I would switch back and forth between being the first to finish our multiplication table speed tests. We were good friends, played a lot of basketball and a little golf. We got plaques at the end of the year, and a lot of applause from teachers & students. I think that's when I knew that you can be smart without being a dork, because we had some of those kids in class too.
Around high school, I had a Tandy 1000-SX PC compatible system, and I was doing stuff with it that a roomful of adults at the Tandy Users Group couldn't do (namely, get an MFM hard drive operating in it). I made a very roughly coreographed graphics display, timed to Joe Satriani music, with a friend (Amiga user), for a computer show at the mall in our town. The Amiga pumped out CD quality stereo sound, and he had crap speakers. I convinced the local Radio Shack to give us some decent Optimus tower speakers and an amp, along with some of their plaquards. That whole period taught me that A) I had a future in technology, B) I really liked multimedia - not just video, not just audio, but both, and C) I could probably do PR
kind of stuff, because a 14 year old kid is convincing a store manager to loan him about $1,000 worth of audio gear to connect to a computer he doesn't even sell in his store.
When I was 20, I had just finished DJ'ing at a club where a friend of mine was a bouncer. They needed someone last minute, so I said why not (even though I couldn't drink). We got done about midnight, and my girlfriend at the time had a curfew of 1:30. She was waiting for me at my apartment - asleep. On the drive home, I knew she'd be there, and I knew I was as lucky as I could ever hope to be that this was the case. I woke her up and proposed to her. The next day, I called to ask what her friends at work had said..."I haven't told them yet." Why not? "I thought it was a dream!" 14 years later, we're still happily, happily married. It's neat to know you found the one...she gives me all the confidence and support in the world, and I'm probably not worthy of her (although she's said otherwise).
Good idea for a thread, Sly.