Best of Luck Mokusou, skateboarding seems like a lot of fun, I always wished I could, but never had the balance or dedication to learn.
Just a quick note, if you are referring to skateboarding. The acceptable term is to ride skateboards or to go skateboarding, not to play skateboard.
Just a little tip for you

This pasttime is very socially and attitude based, so some might ignorantly judge-- hope it helps and enjoy