I Started Longboarding At 38 And Now I Longboard Everywhere

John Tan
2 min readOct 19, 2021

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I picked up longboarding last December when I was going through a bout of depression. I was cycling along the waterfront near Marina Bay Sands when I ran into my friend Dan on his longboard. A grown man on a longboard just felt like freedom. The very next day, I went to Longboard Love and picked up a Zenit longboard. This is the story of a middle-aged man rejecting the cliches of golf and MAMIL (no disrespect to all you golfers and cyclists out there) and picking up a sport better suited for 18 year olds than 38 year olds.

Learning a semi risky sport in middle age makes you feel 20 years younger.

For those of you who don’t know what a longboard is, just imagine a skateboard but much longer. A longboard has four wheels and doesn’t work on water (you’re probably thinking of a wakeboard or a paddle board). The reason why longboards are so long is because you can dance on them. I’ll explain longboard dancing later, but first I have to tell you how excited I was the day after buying my longboard. I took Prince (it’s a purple board) out for a ride by the waterfront where I ran into Dan and kept going for nearly three hours. I was a complete beginner who had watched a couple of YouTube videos the previous night, and there I was riding my board like I knew what I was doing. At the end of that first session, about two hundred metres from where I parked my car, I had to go down a slope. Going downhill wasn’t in any of the videos I watched, but after three hours, I was feeling pretty good about myself on a board, so I decided to go for it. The first couple of seconds was pure adrenaline, then panic set in when I realised how fast I was going. My body tensed up, those four tiny wheels started wobbling, and the next thing I knew, I was lying in a heap bleeding profusely from a scraped elbow.

Learning anything new is all about trying, failing, picking yourself up, and doing it all over again.

That disastrous first session didn’t put me off longboarding. I bought elbow and knee guards, found myself an instructor, and started taking weekly lessons with Dan. I also began following longboarders on Instagram and spent hours admiring how graceful they are dancing on the longboard. Peter Pan, Cross Step, Chop The Wood — I started learning different longboard moves with coach TC. Attempting a new trick for the first time is always scary, but every single time I got over the fear, and the determination to nail the trick wins out. Ten months after picking up longboarding, it’s become my favourite way to get anywhere. Next month I’m bringing Prince with me on a road trip to Costa Brava and Côte d’Azur.

Sun. Sea. Freedom. Here we come.

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John Tan
John Tan

Written by John Tan

Deep in the future of work & learning | Obama Leader

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