As you learn to ollie, begin trying it up and off obstacles. You’ll need a place where concrete sidewalks or similar platforms are bordered by lower concrete surfaces, like in a parking lot. You do not need to have ollies mastered to begin learning to do this. Some skaters’ first ollies are done jumping off a curb.

You need to approach an obstacle with enough speed for your entire board to clear it when you’re in the air. If you land on the obstacle, you will fall. Concrete isn’t like snow or water. It is unforgiving and it is not your friend.

To ollie up something, approach the obstacle with speed and, before you reach it, jump. You’ll want to be high enough in the air so your wheels clear the lip (front edge) of the curb. Remember to slide your front foot up the board. Think of your foot as a paint bush, and use the side of your shoe to paint the grip tape. This is another basic YouTube video showing how to olie up and over obstacles.