How to Ollie Over an Obstacle- A Visual Guide

Doing an ollie over an obstacle really is the test of whether you have your ollies down or not. It isn’t uncommon to hear people complain that they can ollie while moving, but can’t ollie over an obstacle like a water bottle.

This means that they are psyching themselves out when they ollie or their ollie has bad form. Either way, learning to ollie over an obstacle is great fun and good practice for tightening up your form.

Let’s go over the basics of how to ollie an obstacle.

Timing the Ollie

By now you know how to ollie.

The only trick with doing an ollie over an obstacle is that you need to time when you start your ollie, be moving fast enough to clear the object and keep good form. I guess I should add that you can ollie higher than the obstacle itself. No one is doing an ollie over a house.

Timing when to start the ollie can feel a bit tricky, but it really isn’t.

You need to keep your eyes on the object as you approach and not your board. Sorry skaters who stare down as they do tricks. Time to break that bad habit.

Crouch down as you approach the object. Right before your front wheels would make contact with the object, pop your board up for your ollie. This can take time to get the feel for.

Sometimes, if you pop too late, the nose of your board will hit the obstacle. This can also happen if you’re going very fast and you don’t pop early enough.

ACTION STEP: Start by practicing controlling when you pop by popping your board exactly at a crack in the pavement. Crouch down before you reach and pop the ollie right before you reach the crack. Do this 20 times.

If you are curious what a poser is and how to not look like one, then check out my tongue-in-cheek guide here.

Move Fast Enough to Clear the Obstacle

Next, you need to be moving fast enough to clear the obstacle in the time it takes you to ollie and come back down.

If you are only doing an ollie over a crack in the pavement, then this isn’t very fast at all. However, if you are doing an ollie over something longer like a cement block, then you will need to go faster, Generally, the longer the ollie you need to do, the faster you need to be moving. This is something you’ll get a feel for with practice.

So, you need to have ollies with good form even at higher speeds.

ACTION STEP: Practice doing some ollies at higher speeds before you try and ollie over something. See how fast you can go and still comfortably ollie. Work on doing clean ollies while moving fast during each skate session.

Start with Small Obstacles Like a Water Bottle

As with most things in life, progress comes slowly and steadily. You need to crawl before you can walk.

This means you will start by doing ollies over short and small obstacles. Something like a stick is perfect at first. The point here is to build up muscle memory and build up your confidence with doing ollies over obstacles. As you get more comfortable, you will practice doing an ollie over higher and higher obstacles.

You’ll probably find that trying to ollie over something will bring out your worst habits. This is a good thing and it will force you to improve your form.

ACTION STEP: Find a stick. Place it on the ground. Roll up and try and ollie it. Do this 10 times and video at least one attempt to watch later.

Look at the Obstacle, Not Your Feet

Looking down at your board whenever you do a trick is a bad habit.

It looks awkward and makes it harder for you to direct your board’s direction with your shoulders. So let’s stop that bad habit now.

It will take a session to get used to not looking at your feet while you ollie, but you will learn quickly. It will honestly start to naturally happen as you begin to ollie over obstacles because you will want to watch to see if you’ll accidentally run into it or not.

It’s good to practice this a bit without doing an ollie over something first to get the basic feel for it.

ACTION STEP: Do 20 ollies with your head up and looking forward. Do these ollies at various speeds.

Keep Centered Over Your Board

This is one big issue I had when I started to ollie over things.

I would want to lean forward to clear the obstacle or lean back if I thought I couldn’t actually ollie it. Both of these habits made doing an ollie over something very difficult. Sometimes I would land it, but very awkwardly and my front wheels would come down earlier than my back wheels. My bad habits really started to come out.

The best way to get height and way to clear an obstacle is to keep your shoulders level, stay centered over the board, and just time your ollie right as you approach. Nothing special happens with your shoulders and you shouldn’t be leaning or turning in any way. If you are, then you’re just psyching yourself out.

ACTION STEP: Video yourself as you ollie over something small. Are you staying centered over the board or are you leaning forward or backward?

If you are having trouble with turning your board while you ollie, you can check out my specific visual guide to start turning your board once and for all.

What Are Good Obstacles to Practice With?

A curb is a great place to practice doing ollies up obstacles.
  • Curbs
  • Sticks
  • Skateboards
  • Waterbottles
  • Grind Rails
  • Anything Really

There actually aren’t too many things that are bad to try and ollie over. Preferably you could move the objects around to better place them, but this doesn’t always matter. For instance, curbs are unmovable and perfect to practice ollies on.

The only caveat is don’t ollie over anything that you can break. So this means no ollies over people’s phones, homies, or expensive cameras. Not at first at least.

Additional Questions

Do Risers Help You Ollie Higher?

Everyone wants to ollie higher and there are some rumors on ways to do so. For instance, risers are a plastic part that creates more distance between your wheels and your board. Well, do risers on your skateboard actually help you ollie higher?

Putting risers on your skateboard increases the distance between your wheels and your board which does two things. It raises your center of gravity slightly and allows you to have a higher pop. For these reasons, putting risers on your skateboard can help you ollie higher. However, risers won’t have a very dramatic effect on your ollie height so don’t expect to add inches to your ollie.

Honestly, if you can’t ollie that ledge without risers, you likely won’t be able to comfortably with risers on your skateboard. I would focus on improving your ollie form and getting stronger to increase your ollie height.

If you want more practical tips that can improve your ollie height, then check out my visual guide with action steps to improve your ollie’s height.


So that’s it about doing an ollie over an obstacle.

There are some tips to keep in mind and ways to practice, but really there’s nothing new here. Most people just psyche themselves out and lose their good form for their ollies.

Luckily, practice will take care of those nerves and you’ll be doing ollies over obstacles in no time.

Anyway, I hope this article helped. Thanks for reading, and look out for more material from Board and Wheels.


I have other guides about doing an ollie meant to specifically answer different aspects that might be helpful for you. You can see my list of ollie articles below:

Otherwise, learning how to ollie takes a lot of time and dedication. It can also help to get other perspectives and see other guides so you can get a really solid understanding of how the ollie works. You can also learn different tips and potentially find one that really helps things “click” for you.

Below are some great guides that I think are strong in different aspects. Check them out:

Board and Wheels

I am a tech guy who skateboards and longboards for fun. I started skating in elementary school, quit in highschool, and started again in grad school.

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