Whatever you do, don’t give up. Keep trying. If what you’re doing isn’t working, try something new. Skateboarding is all about experimenting with new ideas and finding out what works. Keep tweaking your results until you get what you want. Watch as many trick tip videos as you can, get advice from good skaters, and remember to enjoy yourself. If you don’t give up and you keep trying, eventually you’ll master the Ollie. Don’t let it frustate you, it takes time and lots of practice.
Now, I might not be able to skate to save my life, but I can do a little physics. So here's a thought - maybe I can use physics to learn how to do an ollie. Here's the plan. I'm going to open up the above video of skateboarder Adam Shomsky doing an ollie, filmed in glorious 1000 frames-per-second slow motion, and analyze it in the open source physics video analysis tool Tracker.
This is how I learned how to ollie. Place your skateboard next to a curb, right up against it. This will help keep your board from rolling. Next, do everything that I just described, but don’t worry about what your board does. Just do it, and land up on top of the curb, on the sidewalk. Don’t stress about whether the skateboard will be there, or if you will get hurt – just go through the motions of ollying up the curb. If you do it right, the skateboard will be there. If you do it wrong, you’ll probably just land on your feet on the sidewalk. Here’s the key – just do it and expect it to work. Your body understands what you are trying to do, and the less you stress, the more it can kick in and fill in the blanks.