Wow. Cool bunch of stories...keep 'em coming.
Me:
Grew up around a restoration shop (Dad's) for old Brit/German/Italian iron. Changed cities for college, found a fairly well-known (nationally, oddly enough) Alfa Romeo shop about a block from campus, and worked as a restoration tech on afternoons and weekends for three years or so, learning as I went. Eventually graduated with an English degree (Journalism minor) and didn't really know what I wanted to do with myself besides writing...and knew writing probably couldn't pay the bills. Given that, I kept on wrenching on Alfas.
Circumstances changed, and I switched shops, working for a little while as a Porsche/Vespa mechanic (local P-car independent shop was also the local Vespa dealer). Hated the Vespa side of things, and once it looked like it was going to be my only focus (no one else there would touch the things), I picked up and moved to Chicago to be with some friends. Without any real direction, ended up working as a BMW tech for a friend of mine who owned an independent shop there.
Oddly enough, that prompted a pretty heavy involvement in the national BMW car club (BMWCCA). Had done a bunch of newspaper/A&E/car club freelance writing through college as a lark, and after some time, I landed a regular gig with the CCA's national club magazine. Two years later, thanks to a near-endless amount of hard work, my nearly four-year-long job search paid off: I found the job I've got now. I'm assistant editor for a fairly well-known car magazine (no, not that one; the other one) in Ann Arbor, Michigan.
All things considered, even though the honeymoon's long over, I absolutely love it. I come to work every day, hang out with crazy, ridiculously intelligent people, and get to play with cars and travel for a living. It's the career I wanted when I was twelve but never thought that I'd get. I'm 25, thoroughly geeked on both my job and its subject matter, and I feel pretty damn lucky...