If you are skating by yourself, go your hardest.
But if you are at the park or a spot with others cruising around its lame as fuck. Parks are dangerous places and people collide all the damn time even when they can see and hear everything around them. With headphones in you're not doing yourself or anyone around you any favors.
When you skate with friends and they have headphones in, it's fucking irritating. We're supposed to be hanging out, having a laugh while skating. I shouldn't be constantly competing with the music playing and acknowledged with an annoying "What?" every time I want to congratulate you on a trick.
We may as well skate by ourselves if all we want to do is listen to our own private music.