For me, skateboarding dreams are the equivalent of what flying dreams are for most other people. I feel a sense of freedom and elation that is stronger than in dreams when I actually am flying. The skateboarding segments of my dreams are usually rather short. I manage to do a few crazy tricks -moves that I long to do in reality but am unable - and then my board will turn into another object, like a milk carton or a plastic tray. Othertimes the deck just goes all soggy beneath my feet, and my wheels melt, or I look down and realize that I have misplaced my shoes; then the skateboard portion of the dream gets forgotten and the narrative turns into a quest for lost footwear.
Once I met Rodney Mullen in a dream. I was doing some strange nose wheelie trick, and the veteran freestyler came up to me in a freindly sort of way. Maybe I shook his hand or asked for an autograph, but then he knocked a box of wax crayons off of a shelf, and they scattered all over the floor making further skateboarding impossible. In pondering this dream I wonder if it points to a link between skating and creativity? Or was my unconscious trying to say that skateboarding is like "child's play" and something that should be left behind? Maybe Rodney's gesture was my unconscious dismissing my skateboarding efforts as being primitive and childish. I often suspect that the meaning of dreams is blantantly obvious but I don't want to listen to what they have to say, so I pretend not to understand.