I started out riding in high school and never wore cycling shorts. I rode a steel 24" Huffy 10sp pretty much daily. It was way too small for me, but I didnt know that at the time. I never worried about how fast I went, I was just out to enjoy the scenery and get out of the house. My tires weren't very skinny and I think I ran them around 50psi. I have no idea how many miles I rode back then, I had no computer and didnt really care.

About halfway through college, I moved out of my parent's house and into the one of the most uncycling-friendly cities I know of, leaving my bike behind. I didnt get back into cycling until about 3 years ago when my wife an I bought some cheap-o walmart bikes. Shortly after moving to Fort Worth, we discovered a lively cycling culture right in our neighborhood. We started riding more and quickly realized our bikes weren't going to last long.

Now, I'm almost 40, have lost about 30lbs since we started cycling.
I wear spandex on my daily commute because I have to change when I get to work anyway, so I figure I might as well be as comfortable as possible. Yes, I notice the difference in comfort.

I "clip in" with spd-sl shoes and pedals because I like the feeling of a very solid connection to the bike.

I push myself much more often than I did when I was younger because I enjoying seeing the results in being able to go faster and longer on my bike. I still need to lose another 20lbs or more, so I will continue pushing myself. I also like to go on a long bike ride with friends and not be in a hurry and just enjoy the day.

my tires are 28s - not skinny, but not exactly fat.

I don't care who passes me or who I pass.

I ride a steel road bike, but I try to keep it reasonably light. I pack as minimally as possible regardless of if I'm commuting, going for a fast ride, our going camping.

If I worried about my appearance I would never set foot out the door wearing spandex