I got my first bike, a hybrid, in 2010. My (then fiancee) and I would go on leisurely rides around the neighborhood and I would be astonished at the occasional 27mph on a downhill section. A couple months later a few guys from work rode and had road bikes. They encouraged me to come along with them on a ride with them. We went 15 miles. I got home and laid on the floor for 30 minutes unable to move. It was then I knew I had to have a road bike.
I devised a plan to buy a NOS Trek 1.2 from the LBS and was happy with my 17mph average rides on my 7-10 mile route. A different guy at work introduced me to a local team and said I should go on one of their group rides. I showed up to a Wednesday Night Ride and was informed it was their 'fast' ride. I was coached how to draft, keep gaps small, not to yo-yo by a few of the other riders and while I was hurting, I thought I was doing okay by keeping up on the way out. Unbeknownst to me, the real ride starts after the 'turn'. I was dropped like I was on a big wheels in less than a mile. I got to ride the 15ish miles back home solo feeling exhausted. But I wanted more.
I started showing up to their slower-but-longer weekend rides and put in solo miles during the week. Our team leader quickly convinced me to sign up for the local crits a few months later. I resisted but eventually gave in. I "trained" my butt off for the two months and still got pulled halfway through each 40 minute Cat 5 race. I think I raced a few more crits later that year but I don't remember them as well as my first few. I've been a racer ever since. Given my middle-of-nowhere location, races are hard to come by and given my limited time to train I'm probably a Cat 4 lifer. I've had a few top 10 finishes in some crits and even though I prefer them, not that great in Road Races. If I could race every other weekend without driving 2.5+ hours each direction I could probably make it to Cat 3 just by sheer persistence. But life limits me to 5-6 Road/Crit and 3-4 CX races a year.
I still enjoy racing and use it as a constant motivator to keep riding and stay in shape. I've never lost confidence that I could do something great in a race. Even though I haven't seen the results yet, I still come back for more. Along with that, I've lost 25lbs due to riding and eating better since I started. I'm in the best shape of my life and I'll never trade it for anything.