I was a teenage skateboarder… I skateboarded a lot for quite awhile, on into my early twenties. It got to be too hard on me knees when I tried to pick it back up again a few years ago, but I’ll still occassionally ride one, without doing a lot of the jumping tricks.
Often I have dreams where my mode of transportation is by skateboard. In these there is always a feeling of fun and excitement (perhaps because I feel comfortable on one).
A few of my own skater associations: it’s a renegade sport. While snowboarding has made it into the olympics, skateboarding has yet too. There is a certain anti-authoritarian streak in skateboarders because we often get kicked out of places where we like to skate. It is a Do-It-Yourself activity, and fiercely independent. The exhiliration of skateboarding comes from mastering the manuveurs yourself. While there may be competitiveness among skaters, to me it was always about the thrill of riding over pavement and concrete on a board, and being able to manipulate that board at high speeds to make it do what you want, popping ollies and grinding curbs, flipping the board while you float through the air and landing back on it to keep riding.
When I fall, I get up, shake myself off, and keep going. Most of the skaters I know have sustained massive injuries -broken legs & arms, painful bruises, gouges as gravel digs into the skin, and yet when they heal they get back out and do it again. I still think like a skater and dream like one too.