Alright, decided I was gonna finally learn this ollie thing. Been putting it off, you know how it is. Looked simple enough when you see others do it. It ain’t.

Getting Started – The Awkward Phase
First thing, just stood on the board. Felt weird trying to stomp that tail down while also thinking about sliding my front foot. Like rubbing your stomach and patting your head, but way harder ’cause you’re trying not to fall flat on your face.
Spent maybe the first whole session just trying to get the pop. Just that. Stood next to a fence, holding on like an old man. Pop. Pop. Pop. Most times, the board just shot out from under me. Or I’d pop it and forget everything else. Felt pretty dumb, honestly.
Finding the Motion (Sort Of)
Okay, so popping got a bit better. Still felt unnatural. Then came the foot slide. Watched some folks do it, looked like a smooth flick up the board. My attempt? More like a jerky scrape. Tore up my shoe pretty good on the grip tape right away.
- Pop the tail down hard.
- Jump kinda straight up.
- Slide that front foot up towards the nose.
Sounds easy on paper. Doing it all at once? That’s the trick. My timing was all over the place. Sometimes I’d slide too early, board wouldn’t pop. Sometimes I’d pop fine but forget to slide, board just kinda jumped straight up and hit me in the shins. Yeah, that happened more than once.
Little Wins and Lots of Practice
Then, one time, it happened. A tiny little hop. Both wheels left the ground for like, a split second. Wasn’t pretty, wasn’t high, but it was something. That tiny bit of air, felt like a huge deal. Finally!

That gave me the push to keep at it. Practiced in the garage, on the pavement. Didn’t matter. Just kept doing the motions. Pop, jump, slide. Pop, jump, slide. Over and over. Some days felt like progress, others felt like I was going backwards. You get real frustrated some days.
Making it Stick
Consistency was the real enemy. Getting one fluke ollie is one thing. Landing them regularly? That took weeks. Still working on it, if I’m honest. Had to really focus on keeping my shoulders square, not leaning too far back or forward. Bending the knees properly before and after.
Started trying them while rolling really slow. Whole different ball game. Felt like learning all over again for a bit. Falling hurts more when you’re moving, even slowly. But eventually, those started clicking too. Still not aiming for stair sets or anything crazy, just getting that basic rolling ollie down.
It’s a process, yeah? Takes time. Lots of failed attempts. Lots of just feeling awkward on the board. But you stick with it, piece it together bit by bit. It ain’t magic, just repetition. Still got a ways to go, but getting that board off the ground feels good every single time.