I always liked motorcycles in a vague way since I was a kid. A friend of mine had a small Kawasaki dirtbike when we were in elementary school but his dad wouldn't let me ride it. My highschool English teacher/running coach had a Harley Sturgis edition Dyna Glide, or something like that which was really, really loud, had mag wheels, and was way too big for his wiry Irish frame.
I didn't care for that bike one way or the other until I got injured on a run and he gave me a ride home on it. The feeling of freedom stuck with me ever since.
Then in grad school years later I was taking an art history course on Cubism and we studied machine aesthetics, Futurism, etc., and that got me tuned in even closer to the beauty of machinery. Leaving that class one day I heard this weird whistle-putt coming from behind me and this guy rode by on a gorgeous early 70s BMW R60, black with pinstripes. Ever since then I'd been pining for an R60 and got interested in all kinds of motorcycles.
Ca. 2005-6 I started researching vintage bikes and trolling the local craigslist for ads. The Enfield started to appeal to me for its mechanical simplicity and beauty, and when I found out they were still being made I just had to have one. Figured it was easier to learn how to work on a single, anyway.
Took me about two years to finally scrape together the money for a bike, and I picked up my black `07 iron barrel in September 2008. Best decision I ever made.
My only regret is that my coach died before I could show it to him.
Jeff