I've been lucky enough to play sports my entire life. Through eighth grade it was soccer, flag football, baseball and in high school it shifted to become golf. I was lucky enough to be pretty good at a lot of different sports but not especially good at one in particular (well, unless you count building legos!). That all changed when I dove in headfirst with golf. For me, it was the first sport where I could see the results from putting in the work. Though I didn't recognize it as such at the time, this represented a big step forward in realizing that hard work pays off in time.
I was OBSESSIVE about golf (kind of like with triathlon now!). For my first three years of high school it was practically all I thought about every day. I'd come home from school and go play anywhere from nine to twenty seven holes in the "executive course" that was a short drive from home. There weren't a ton of options for courses in New Orleans (where I grew up and still call "home" ultimately) but luckily my family spent a good deal of time at the beach in Gulf Shores, AL. There were some very, very nice courses out that way and my first job was a cart boy at one of them the summer between my freshman and sophomore year of school. The ultimate payment there was free playing privileges that whole summer. Needless to say, I took advantage!
This trend continued through the end of junior year, at which point I was practically a scratch handicap on a very tough course. I had been looking at schools where I felt I could make an impact with their golf program and even received an offer for scholarship from one school. Then that summer (before my senior year) I participated in a month long, self-contained bike trip from Seattle, WA to San Francisco, CA. Having never really ridden a bike before (I mean, I could ride a bike but didn't go on "bike rides" per se) this was quite the revelation. We averaged 50 or so miles a day for 4 weeks and it was literally the best (or one of) experience of my life up until that point. It was also the longest I had gone without playing the gentleman's game. I got back from that trip and my desire to play golf quite literally disappeared. From that point on I found a new love and it had two wheels.
My senior year of high school I spent the first half riding my bike a decent amount (don't really remember how much) but it was all on a Raleigh mountain bike with slick tires (the bike I had ridden on the trip) so I wasn't going particularly fast but I loved every minute of it. I was breaking a lot of the rules but didn't realize it yet. For my 18th birthday I received a Klein Q Carbon Team road bike (a bike that I still ride and race, 8+ years later!) and started getting a little more serious. I still rode in a mix of spandex shorts and regular shorts with t-shirts and mountain bike pedals. I don't really remember at what point I actually got real bike clothes and shoes, but it was sometime before college.
When I started at William and Mary I immediately found the cycling club and that's what I did through college (well that and TONS of intramural sports). The road biking season began in late February and ended in April or May and for the first two years I participated in almost every weekend of racing. I got to be pretty good but got a little bored and my junior year didn't ride or race quite as much. I even stopped shaving my legs at one point (gross). I got motivated again during Christmas of my senior year and raced again in 2007 but was never quite at the level I was during my sophomore year.
Upon graduation I spent the summer in Williamsburg doing a whole lot of no riding and then moved to Charlotte, NC to work for Habitat for Humanity as an AmeriCorps (which I did for 2.5 years) and I ran a little bit that fall for the first time. I posted a solid 19:30ish 5k then stopped running because I was crushed so bad! In January I resolved to get back in shape and started taking running a little more seriously. I ran a decent amount from January to April then I was convinced to start riding my bike again, which was a painful process. At that point, the only thing left was to start swimming so - with great resistance - I began swimming in June or so of 2008. At that point I started considering myself a triathlete and the rest is mostly history. My first triathlon was in April of 2009 (half-ironman, DUMB!) and I've seen good progression since that point.