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5 Big Lessons Skateboarding Taught Me About Business

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As a teenager I was a “skater.” One of those kids who hung out downtown and annoyed the pedestrians. Skateboarding is how I spent my teenage years. Was I any good? I like to think so. Towards the end of my skating days, I almost got my 360 flips dialed in, used to launch myself straight off huge sets of stairs, and even landed some pretty big backside heel flips off a dip in the industrial park. This was in a time when there were very few skate parks so we had to make due with our surroundings.

In many ways, spending most of my days skipping class and hanging out with my friends laid a solid foundation for the way I look at business today (my parents may have a different view on this):

1. Focus On Your Passions

Winchester Skate park pool Judi O

Ask my parents and they’ll tell you how much I loved skateboarding and hanging out with my friends – maybe too much. There were times I’d jump on my bike to pedal 10 kilometers for a 2 hour session with some friends. Then there were those days I would get a new skateboard board… I would be so excited, I’d sleep with it next to me so that when I woke up I could see it was real and that I wasn’t just dreaming.

Passion is a powerful force. If you’re in a business that you’re absolutely passionate about – the work, the long days and the late nights just get easier. With passion, persistence never wavers and even on the darkest days – and they will come – you’ll be able to plow forward.

Since turning 19, I’ve been very fortunate that I have only done what I’m passionate about. My advice to you is to find something that lights up your passion and the money will follow!

2. Take Risks and Go Big!

Unity Day

There were countless times while skating when I was confronted by a new set of stairs or a drop and someone would ask, “Hey, Dan – are you going to do it?”

As I got more skilled and more confident, “YES!” became my go-to answer, even if I was scared shitless.

Don’t underestimate me when I say that I was scared shitless. I’m talking deep-down, dread in the bones scared, like if I don’t pull this off I’m going to be hurting bad. But you know what? More times than not, it worked out. Maybe I didn’t always land it well or even land it at all, but I didn’t wind up in the hospital and on a few occasions, I actually pulled it off. Nothing feels better.

Like going for the “big land,” entrepreneurship is about risk. The bigger the risk, the bigger the reward. What skateboarding taught me was not to sell myself short – we’re all capable of bigger and better. Of course, on some days you will come up short, but if you get up and try again, you may just land it – and it’s on that day that all the other falls and “fails” that came before, will finally feel worth it.

3. It’s All In Your Mind

Lost In Thought

Push, push, push, setup and go… you’re in the air, you flick the board and BAM! You miss the grip and come up short, crashing hard. You get back up, brush yourself off, stop, look at the terrain and visualize how it should be done. You close your eyes and try to “feel” how it should feel, picturing your landing being executed perfectly.

That’s how great skateboarders do it. Guess what? Business is no different. Even today, I stop, take out paper and sketch things – situations, environments, outcomes – and visualize the outcomes I want. Whatever that may be – a happy customer, positive reviews, someone saying “yes,” or a building full of amazing and talented people creating a huge amazing company.

Ten years later, even though I still bare the scars, I’m doing it the same way.

4. Show Some Style

Style

Landing the trick was one thing. Looking good at it was another. Some skaters I used to ride with had great technical skills, but lacked style. It reminded me of watching a robot skate. Impressive, but lacking soul.

Contrast that with a skater who can not only ollie, but who can ollie with style – and that’s a skater who makes you stop and stare. In business, there are thousands of ways to make pure cash, but in my mind, you need to have style, too. It’s about how you did it and how the people around you felt. Adding style to the way you do business will make the world stop and stare – and it feels great when they do.

5. Progress And Progression

Parkour Team

Nothing progressed my skills more as a young skater than just hanging out with the older, more talented skateboarders. They took me under their wing, showed me things I never thought were possible  and most importantly, encouraged me along. There were moments when my landing even the simplest trick was a reason to celebrate – both for me and for them – it was all about progression!

As long as your business is progressing, no matter where you start, it’s a reason to celebrate. I’m still reminded of that when I meet a first time entrepreneur who’s launched a new business, raised funding or made a key hire. I get stoked for them, even if it’s a little progress, just like my skating mentors did for me.

Life teaches us good lessons when we pay attention. I still enjoy learning how things work (or don’t work) and to see which ideas are worth emulating for my own business. Skateboarding was my launching pad and I’m forever grateful that my parents supported me, even when their better judgement might have told them otherwise.

What sport, industry or situation have you drawn inspiration from for your business? Leave a comment below with your answer.

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