I’m on a skateboard! Now it’s time for action. Or at least … movement

Why do I walk everywhere when it’s possible to glide nonchalantly? Perhaps because I don’t know how to skateboard – so I geared up for the skateboarding class on the Manly foreshore in Sydney.

I knew very little about the action sport except that, according to videos on the internet, it’s something that both dogs and babies can do.

I do know that skateboarding was once called “sidewalk surfing” because it was an activity that surfers did when they weren’t in the water. It feels like an appropriate name for what we’re about to do, because the hot Sunday afternoon foreshore is heaving with a sea of beachgoers: people walking their tiny dogs, kids on bikes. The perfect environment to add four people who are learning to skateboard for the first time.

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Here we are, freshly kitted in helmet, elbow and knee pads, and wrist guards. When the instructor – Dylan – hands out the protective equipment, it occurs to me that an activity that needs protective equipment means the possibility of falling. It suddenly makes sense why I haven’t learned to skateboard earlier: the metaphorical elbow and knee pads of self-protection have kept me out of risk’s way.

But this is summer, the perfect time to try something new and risky. It’s what’s brought 30-something-year-old Warwick here, one of my fellow students. “I once heard that if you haven’t tried to skateboard by the time you’re 21, you’ll never do it,” he explains. “So my wife bought me a gift voucher.”

Dylan begins the lesson by giving us each a cruiser board, which is a slightly longer board than a regular skateboard, making it easier to learn with. He begins by pointing out that the front of the skateboard has four bolts on it, arranged two by two.

“The first thing is, whether you’re a pro or a beginner, when you put your forward foot on the board, you always cover the bottom two bolts with your toes, and leave the top two showing,” he says.

I place my left foot solemnly on the board for the first time, knowing that so far on this journey, Tony Hawk and I approach skateboarding in exactly the same way (except he is right-footed).

It will be the last time that Tony Hawk and I have anything in common. Unless he also feels vulnerable when he takes his right foot off the ground and places it above the back wheels, in line with the wheels, resulting in both feet on the skateboard.

To my surprise, I don’t wobble too much, and am even able to follow Dylan’s instruction to pivot my left foot so that it’s now parallel with my right.

“Keep your chest between your feet and you won’t fall over,” he says, sharing advice that could also apply to walking.

While I am not yet skateboarding, I am on a skateboard! And now it’s time to put the action into action sport. Or at least … movement.

The aim is to have my left foot in starting position and then push off with the right foot before placing it on the back of the board and then pivoting my left foot. While the skateboard is moving. It’s the opposite of the wise advice friends give me when I’m overwhelmed with work: “do one task at a time”. This is “do all the tasks at once”, and frankly, I’m confused.

It makes me realise how rarely I give my feet instructions. We haven’t spoken in ages; any communication feels like it happens on auto. But after a few false starts and a decision to momentarily not think about falling, I have both feet on the board and roll forward about a metre. I’m one metre closer to nonchalant gliding!


Well, kind of. With repeated attempts, I can soon travel two slow metres. But when it comes time to learn how to turn, things … take a turn. Dylan teaches us to put our weight on our toes and to put our weight on our heels in order to make a wide turn around a tree.

On my first attempt, my skateboard catches on something on the ground and I fall, skidding on the pavement with my hands and knees. It’s okay; the biggest ouch is in the form of embarrassment. But things do go downhill from here (not literally, thanks to the incline-free foreshore).

While the others make their way around the tree in an elegant circle, I simply veer slightly towards the tree. It appears that I can only skate in a straight line, maximum two metres at a time. But Dylan’s parting wisdom makes me feel better.

At the end of the lesson, I ask him how skaters make everything look effortlessly cool. “I’m not really sure. I’ll have to send that question up to the skater community. But when you know what you’re doing and you’re not anxious about where to put what, you just … do it. And there’s an ease to it. Like, you did a lot better at the end of the hour than at the start. So maybe it’s about practice,” he says.

As we glide into a new year with new possibilities, I’m definitely on board with that.

• Jennifer Wong is a writer and comedian. Her new stand-up show, Jennifer Wong Has No Peripheral Vision, is playing in Adelaide, Melbourne, Sydney, and Perth in 2023. Tickets at