5 life hacks from skateboarding we could all use

Matt Humphrey

September 9, 2020

Being freelance is difficult – it takes perseverance, creativity, self belief and innovation. So does skateboarding, so let's learn from it.

Over the last 5 years of growing our startup Curtain Call, I have often thought about what it takes to be an entrepreneur, and tried to draw parallels with other passions – like skateboarding. There are high times and bleak periods throughout the journey, and sometimes it can help to look at it through a different lens.

Of course, everyone’s journey is distinct – whether you are a business owner, freelance creative, or working for the man, these 5 life hacks should serve you well, on or off your board.


No-one who has ever been successful at anything has given up after they fall or hit a hurdle. Who ever saw a skateboarder, or surfer, or snowboarder fall off and then immediately pack it in and walk home? No-one. The same is true of any successful sportsperson, artist, or business owner.

Failure is an important and inevitable part of the process, and you have to just keep on at it, dust yourself off, and get back on the board. Falling off does not mean you have got it wrong, it just means you need to do it better or differently in order to stay on the board longer. Running a business is no different, we learn from our mistakes and we improve. My co-founder John is always telling me to fail fast and often – which is apparently a mantra for NASA too.

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times I’ve been trusted to take the game winning shots and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

Michael Jordan

Michael Jordan talks about the shots he missed, and how they drove him to success. Whichever way you spin it “Fail forward”, “Fail often”, “Fail fast” – the message is simple that you have to give it a go first, no matter what the outcome – then keep going.


I remember getting my first skateboard when I was 7, and seeing other kids do olly kick-flips, and other combination tricks and trying to work out how to do them, and if I ever would. What I hadn’t realised was that I first needed to master an Olly – a simple, yet crucial first trick that would open up others along the way.

When you have a passion (business or otherwise), it is easy to get carried away with the opportunities and ideas of how you could progress. The most successful people and companies got to where they are by doing one thing, and doing it super well. You can break this down to focusing on short term objectives, and even daily time management – the important thing is to focus, and not be distracted by shiny objects in your periphery. All of this is nicely summed up, and repeated several times over in the brilliant ‘The One Thing’ book - highly recommended (to all, not just business people).


Ok, so somebody may have done something ‘similar’ before, but you know that you have the secret sauce to do it better, faster, more effectively, whatever it is. That’s because no-one else is you or has your perspective. Strive to be different, and you will achieve something different - you may even surprise yourself with what you can achieve.

“If you’re always trying to be normal, you will never know how amazing you can be”

Maya Angelou

Your own style and identity are key to establishing your brand, and can also go a long way to reinventing the wheel. Skateboarders and snowboarders have repeatedly added their own creative flair to existing tricks, in order to invent new ones – these sports are no strangers to it, and nor should your business be.


Whilst it is important to be able to see opportunities where they exist, and look for alternative perspectives, it is equally so to have the confidence in what you are doing – to own it.

You had the original concept, you’ve created the product, business, trick, or artwork, and it is yours. No-one else knows it like you do, and no-one else has spent as much time on it as you. That means that when it comes to it, you need to hold your own and perform it just how you believe it should be. 

There is truth in what Shakespeare (and countless others have) said about staying true to yourself. This allows you to perform your trick, or business, with integrity but also with your own distinct flavour of panache.

“This above all: to thine own self be true”

William Shakespeare

Others will challenge you along the way, especially if you are being disruptive, but you’ve got this, so stand your ground. This confidence will shine through and help you to perform as best you can.


Rules are there to be broken right? Sure you can stick to them and live a life within the same parameters as everyone else. But you are not everyone else. You are an entrepreneur, an artist, a trickster, and you are going to do things differently. You have seen how everyone else is doing it, and realise that you could just go along with them, do the same thing just like everyone else.

It is so integral now in startup culture to be disruptive, otherwise you won’t make an impression or achieve that colossal high growth that we’re all after. The only way to do that is by breaking the rules, reinventing, and taking a risk. Sure, it might not work, but you’ll have at least had fun along the way.

Just because something has not been done before does not mean that you can’t do it. Believe in your vision, hold your own and innovate – the world will thank you for it, and so will you.

Matt Humphrey is a photographer, and co-founder of Curtain Call. Photography site: www.matthumphreyimages.com

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