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Fail to win: Why the overnight success story is the biggest myth out of them all

 Show me an overnight success story, and I will show you a 10-year back story of failure.

The ‘failure’ bit is a vitally important part of the ‘success’ bit. Without learning from what we fail at, an overnight success would never happen – but we don’t talk about the fail part. The word itself – failure – is supercharged: going all in and losing everything on a big call. Complete and utter despair and destruction. Crash and burn, loser.

Or, in a reframed perspective, it can just mean successfully crossing off another item from your shit-to-try list.

I have had a couple of overnight successes. Vend is a 10-year ‘overnight success’. The Pam Fergusson Charitable Trust, the charity I launched to help kids learn technology, is a five-year ‘overnight success’. Both of these ventures have had multiple stare-into-the-abyss moments. I can tell you stories that will make you twitch. And from all my experience, I have learnt that failure is inevitable and being comfortable with it is when you personally develop the most.

Firstly, you can usually avoid the crash-and-burn of failure, most definitely survive it, and secondly, who the fuck cares about anyone who might call you a loser for trying? Should you take risks and try stuff? Yes. Should you bet it all? Hell no.

Jeff Bezos, my arch nemesis in retail and producer of phallic space rockets, looks at decisions and the risks associated with them as a choice between doors. Most good decisions are a two-way door, where you can go through the door and should you find the room is full of snakes, you can quickly back out of that shit. You nail the door shut and you don’t open it again. That’s a two-way door type decision where it is easy to reverse it. Some decisions, however, are one-way doors: non-reversible. You step through, the door closes and locks behind you. You are committed to that course, and if you get it wrong, you have to deal with some consequences. I hope you like snakes.

Two-way door decisions should be made quick and all day long. Some will be wrong, but you quickly spot the fail and back out and try something different. The consequences of failing are survivable. On the flipside, you don’t need to avoid the one-way door decisions, as they often have big rewards. You just need to be sure of your decision before going through.

I’ve noticed a common pattern when it comes to making decisions with risk. Often in life, the more time you have and the more options you have, you have many two-way doors to explore. But as time goes by, doors close themselves and finally, when we are forced to make a call, often the only door left is a one-way door. Instead of failing fast and going again, we hesitate, perhaps waiting for the perfect amount of information, or the risk to be zero. We procrastinate because we are afraid of failing, but end up without the choice being made for us through a one-way door. It sounds stupid, but we have all had it happen.

I try and live my life taking a lot of two-way doors. Have I failed a lot doing it? Oh, fuck yes. I have had some epic failures. Many ideas that just bombed. But I didn’t stop starting new things and trying. In fact, I’ve learnt to embrace the fear of failure. This has famously manifested itself in me doing an annual impossible challenge. For 10 years, I have picked something that terrified me and then dared myself to fail at it. I’ve cycled around the world, sang on stage for money, ran 1000km, built a hundred-million-dollar venture.

I am no Tony Robbins type guy – I am a below average kid from Pakuranga who was raised by my mum. She was inspirational, though. She raised us kids as a solo Mum bound to a wheelchair, and nothing in her life was impossible. She was not afraid to try things and fail. Most of the everyday things able-bodied people would do each day were potential failures for mum, from getting out of bed, to grocery shopping, to driving a car, to camping in tents in Kauaeranga Valley. She figured, ‘Oh well, I broke my back, might as well give stuff a go because it sure beats sitting around being dull’. She was one epic lady.

My mum inspired me to try things and not worry about failing. Even as a kid, she was always there with some comforting words as I fell out of a tree or nailed my hand to a block of wood. I mean, I knew I had screwed up – the pain was usually a good indicator – but she always managed to make me feel like I could try it again.

One thing that frustrates me in New Zealand is our grotesque attitude to failure and its ugly sibling, tall poppy syndrome. We just love to see others fail, especially when they are doing well. “Pull your head in, cuz!” It’s childish, like they want to say, “Nah, nah I told you so”. It’s depressing to the point of depression for many entrepreneurs and changemakers in New Zealand. It sucks. But fuck them, they are the losers here.

Is it cool to fail? No. Should we celebrate failure? Perhaps not celebrate it, but at least acknowledge the bravery of giving shit a go. I mean, don’t go doing dumbass shit and expect a cake and a high-five. But try stuff, and when you fail, try and make it the two-way door kind of failure. Sometimes you have no choice and you have to go through a one-way door, and that’s okay too. Take a deep breath and go for it. Surround yourself with people who support you, not try and knock you back.

No one just nails anything important on the first try. Do you think Serena Williams just nailed it in her first match? Her first 100? It took her seven years as a professional player to win her first title, then she was “an overnight success” who went on to win 23 titles. Another epic lady. 

I remember this advice someone once gave me. When you are feeling like the world is on top of you, just remember that everyone is fighting their own private battles. We all hide them well, because we are all terrified to be seen to fail. You are not the only one experiencing a quest of imperfection. It’s okay to screw up, and when we do, make sure we look out for each other. Help pick someone up and say, “Nice try, I can’t wait to see you try again.” The more courage we have, then the more options we have to take those two-way doors. Fuck the naysayers, the knockers and the snakes. What do they know about doing epic things, anyway?

Vaughan is the founder of Vend, a New Zealand high-growth tech success story, and founder of OMGTech! a charitable initiative to help kids into careers with future technology. He was EY’s Tech Entrepreneur of the Year in 2014 and is vice-chair of the NZ Hi-Tech Trust, which celebrates the NZ hi-tech industry through awards and education.

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