The Ollie Struggle: I’ve Been Skating for 2+ Years and Still Can't Ollie

Alright, let’s be real for a sec. If you’re reading this, there’s a good chance you’ve found yourself in the most frustrating spot in skateboarding: You’ve been skating for a while, you’ve learned the basics, but for some reason, the ollie still seems like an impossible feat.

I get it. After two+ years of skating, I still find myself struggling with the ollie. It's not that I’m not trying – trust me, I've sacrificed more shoes to this trick than I care to admit. But no matter how much I practice, something always seems to go wrong. Either I kick too hard, or not hard enough. Maybe I forget to suck my knees up like I’m trying to jump over a fence. Or, of course, my board decides it’s just going to stay glued to the ground while I launch into the air with zero help from the wheels.

So, what’s the deal? Am I doomed to be the skater who never lands an ollie, forever stuck in a frustrating loop?

Nope. Here’s the thing about skateboarding: it’s a journey. And the ollie? It’s just one part of that journey. The struggle is real, but it’s also part of what makes landing the trick so damn rewarding.

Let’s break down some tips on how to stay motivated through this relentless ollie struggle:

1. Acknowledge That It’s Normal to Struggle

First off, stop being so hard on yourself. Skateboarding isn’t a quick process. Sure, there are those freaks of nature who land their first ollie in like 30 minutes, but for most of us, the process is a grind. No one’s an expert overnight. The best thing you can do is recognize that struggling with the ollie is part of being a skater. It doesn’t matter if it’s been 6 months or 2 years – it’s OK to be in that space.

Remember, even the pros were once beginners, and they fell a lot before they got it right.

2. Break Down the Movements 

The ollie is all about timing, technique, and coordination. It’s not just a jump; it’s a coordinated movement that involves popping the tail of your board, dragging your foot up, and sucking your knees to get that perfect air. If you’re still having trouble, maybe it's worth focusing on specific parts of the trick.

Start by isolating one part of the ollie. Spend some time just practicing the motion of popping the tail or dragging your foot up without worrying about getting air. Get used to the feeling of the motion so when you finally put it all together, it’s more natural.

3. Celebrate Small Wins

Ollies don’t always have to be perfect to count as progress. If you pop your board an inch off the ground, that’s a win. If you’re getting your back wheels off the ground or your foot is making solid contact with the grip tape, that's improvement! Celebrate these small victories, because that’s how you build momentum.

Take photos or videos of your attempts to track your progress – you might surprise yourself when you look back and see how far you’ve come.

4. Switch Up Your Environment

Sometimes, practicing in the same place over and over again can lead to frustration. If you’re not feeling the vibe of your usual skate spot, switch it up! Go to a new park or even just find a smoother patch of pavement. A change of scenery can sometimes work wonders in breaking the monotony and giving you a fresh perspective on your progress.

5. Don’t Overthink It

Sometimes, the hardest part about skateboarding is the mental block. The more you focus on how you should land an ollie, the more it feels like you’re fighting with your board. So, try not to stress about getting it perfect every time. Focus on having fun with the process, not just the end result.

Skateboarding is a mindset, and the more relaxed you are about your journey, the easier it’ll be to push through the frustrating moments. Take a break, go grab a snack, and come back to it with fresh energy.

6. Surround Yourself with Positive Vibes

Skateboarding is better with friends. If you’ve got a skate crew, lean on them for motivation. Sometimes, just being around people who are working on their own tricks can reignite your passion for skating. You don’t have to be the best; you just have to show up and keep pushing.

And if you’re on your own? Hop online and check out skateboarding communities. You’ll find tons of people in the same boat. Sharing experiences and watching others go through the same struggle can be really uplifting.

7. Remember: The Struggle Makes It Sweet

Landing your first ollie will feel like winning the lottery. And all that struggle and frustration leading up to that moment? Totally worth it. The journey is just as important as the destination. When you finally land it, you’ll remember every gnarly fall, every moment of doubt, and every time you came close but didn’t quite get it.

And when you do land that ollie? Take a moment to soak it in. You earned it.

The ollie struggle isn’t easy, but it’s part of the fun of skateboarding. So keep pushing, keep learning, and above all, keep skating. You got this!

Remember, the best skaters out there didn’t give up on their ollies. They just kept showing up – and so should you.