February 5, 2019 8 min read

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Skating the razor-thin “edge” between risk and reward is something I’ve learned a lot above over the course of my career. I refer not just to my work as COO of an Amsterdam-based startup, or to my previous career as an an international tax lawyer, but to my former life as … a semi-professional speed skater in my homeland, the Netherlands.

Related: How Much Risk Should First-Time Entrepreneurs Take On?

For me, speed skating — which had me flying across the ice at 30 mph — became a balancing act between force and precision, power and finesse. Winning and losing wasn’t defined in seconds; it was defined in hundredths of seconds. You could be in the middle of the fastest lap of your life when the tiniest misstep would send you crashing.

Yet, still, when you’re a speed skater, you make those moves anyway, swerving around the curves of the track to bypass your opponents, no matter what the risk. You don’t play it safe, you don’t worry about being disqualified, you don’t fear the fall. Instead, you anticipate those falls. You get good at them.

Or, more to the point, you get good at picking yourself up again after taking a tumble.

Risk and reward on the ice and off

This is the same mindset I’ve applied as I’ve skated the twists and turns in my current career in cloud communications — the idea that risk and reward are two sides of the same blade.

When I hung up my skates to practice tax law, I found a sense of stability and groundedness in my work. And I loved what I did. But, when I had the opportunity to join a high-growth startup with a team I liked and trusted, I leapt at it. To me, the choice was a no-brainer. The breakneck speed of innovation and the high-stakes, high-pressure environment of the tech world mirrored what I was already used to on the ice.

Related: 11 Quotes on Hard Work, Risk-Taking and Getting Started From Beauty Billionaire Estee Lauder

I understood how to hustle and didn’t fear shaking myself, and our team, out of the familiar — whether we were scaling from a handful of employees to hundreds, or actively deciding whether to take on our first round of funding after six years of steady, profitable bootstrapping.

Yet, if headlines are to be believed, risk-taking for career advancement — especially for women in tech — is easier said than done. A University of Southern California study showed that men tend to take more risks under stress, while female risk-taking under stress decreases. 

Another report, from the Kellogg School of Management and the University of Chicago, found that women, on average, are more risk-averse than men in financial decision-making, which the researchers associated with differences in career choices.

In the report’s review of MBA students, about 36 percent of females studied chose a risky career in finance (like investment banking or trading), compared to 57 percent of their male counterparts. Some part of this may be attributed to the famous confidence gap HP evealedin an internal audit. That gap showed that men will apply for a job or promotion when they meet only 60 percent of the qualifications, while women won’t apply unless they meet all 100 percent of them!

Embracing an athletic mindset

Reading these studies reminded me that my speed-skating days had helped prepare me for my work in technology. The reason is that being an athlete hones your focus and channels your drive and ambition to become a team leader in business. It teaches you to stop setting limits for yourself, and to reconfigure how you confront the challenges that come over the course of a career.

A study by Ernst & Young surveyed 821 high-level executives and found that 90 of the women polled played sports. Among the women who were in C-suite positions, that percentage rose to 96 percent. And that’s great. But you don’t have to be a speed skater, or even an athlete at all, to appreciate risks as opportunities, as you seek out new challenges at work — especially in the high-stakes, high-pressure startup scene.

You just have to embrace an athletic mindset, the idea that not taking risks is actually the riskiest move of all, especially when it comes to your career.

Risk-taking doesn’t mean recklessness.

Cultivating an athletic mindset starts when you recognize that risk-taking isn’t synonymous with recklessness. On the ice and in business, complacency is comfortable, but it also comes with a cost.

If you don’t find new muscles to flex, you’ll never break out from the pack. Risk-taking is necessary for creation and innovation. It’s what makes you pivot when a solution doesn’t address a need the way you want it to. Without pushing out of our comfort zone, we can’t arrive at that next ground-breaking idea. Risk is what enables us to innovate ourselves — to get better and grow.

And the payoff of risk is twofold: 1) You get to find real solutions to real problems. And, 2), you get to explore parts of yourself you didn’t know existed.

That’s how I felt when I left the tax law consultantcy I worked at in my early 20s because a few of the partners had decided to start their own company and invited me to become employee No. 1. It was a big leap but I decided to look at it as a rare opportunity instead of a big risk. “How often do three respected partners decide to start a spinoff?” I asked myself. So I bucked conventional wisdom nd went for it. Great decision.

Go for growth.

Whenever I’ve been presented with a new career opportunity, the first question I I’ve always asked myself wasn’t, “Which job is more secure?” Because no job is secure. Instead, I’ve asked myself, “What will I learn? How much will I grow?”

When in doubt, always choose the growth opportunity, because that experience is one you’ll carry with you throughout the course of your career; it will outlast the personal repercussions you’ll experience whether a startup fizzles or takes off.

I was an established tax attorney and advisor when I was asked to  meet about a COO job at MessageBird (where I now work). To be honest, I took the meeting as a courtesy. But then I actually took the job, because the breakneck speed of innovation and high-stakes environment of the tech world mirrored what I was used to on the ice — and missed. Never mind that the company’s first headquarters was an actual garage whose doorbell didn’t work. Never mind that the staff were engineers in hoodies. The electric feeling in the air told me the risk would be worth it. It was.

Avoid the algorithm approach.

Right now, especially in tech, the world runs on data. We rely on inputs and run the numbers for most of the business decisions we make. But, when it comes to taking risks, especially in your career, there is no algorithm.

Instead the ultimate decision will come down to your “spidey senses” = your brain, your heart and your gut. Trust them. No matter which decision you make, every opportunity, even one that doesn’t necessarily turn out as planned, is an opportunity to learn and grow, if you choose to make it that.

Related: 4 Strategies Used by Superstar Athletes to Become Super Focused

Opt for an “on your mark, get set” mindset.

In skating, as in business, the line-up at the starting line isn’t a prediction of what will happen at the finish. When you’re teetering on the edge of an important decision, there’s always an “on your mark, get set” moment. The trick is to trust your decision-making abilities and determine which risks are worth taking, so that you’re ready to go out and win when opportunity strikes.

I remember one skating race in particular where, ahead of the big day, I was having trouble with acceleration. I couldn’t hold the corner at speed and I slipped. I was frustrated, I was rattled. And during the race itself I could have played it safe but instead I pushed through it. I focused on putting one skate in front of the other. 

And I wound up flying across the finish line.