What Competitive Skydiving Taught Me About Business Risk-Taking

I’ve seen my share of risks in the business world, working as a CEO, CTO, CMO, and CPO at various times in various companies.

But I’ve always been fascinated with the thrills of flight.

At 17, I earned my pilot’s license. And at 18 — despite my parents’ objections — I went on my first tandem skydive. The jump was great, but I knew I wanted to experience the rush of skydiving on my own. Of course, you can’t just hop out of a plane by yourself. You have to work up to that level. At first, you jump from 5,000 feet with two people holding onto you.

At the next level, you jump from 14,000 feet.

My third solo jump — still with people hanging onto me — was from 14,000 feet. And it ended up being one of the most terrifying and risky experiences of my life.

As soon as we left the plane, I found myself in the wrong position. So I started tumbling. My first trainer was ripped away from me almost immediately, and soon after, my second fell away.

At this point, I was flailing through the sky in an uncontrolled solo free fall. The instructors tell you to just pull the cord on your parachute if you find yourself in this scenario. So, I did. But because of my position, it came out in front of me and tangled around my left hand and the altimeter, breaking my fingers.

There I was, wrapped in my lines at 10,000 feet — and falling fast. And I swear time slowed down. I’m not even sure how, but I managed to untangle the parachute from my arm and open it without pulling my reserve chute. After I landed safely, everyone on the ground told me they were convinced I was going to die.

You’d be forgiven for thinking that was the end of my skydiving career.

But I actually went on to skydive competitively for several years. When I quit, I sold my equipment in order to fund my first business. So, in a way, business and skydiving have always been linked in my mind.

Here’s what I learned about being bold in life and business from nearly 800 jumps out of a plane:

Sometimes, you have to do the exact opposite of what feels natural.

On the day of that near-death experience, I learned a very important lesson.

In some situations, you have to do the opposite of what your body is telling you to do in order to survive.

Skydiving instructors teach people to think about their bodies like a badminton birdie. The center of gravity — the rubber portion of the birdie — always falls downward, no matter how you hit it. The center of gravity on your body is around your stomach and hips. That’s the area you should always be pushing down towards earth, letting the rest of your body float upwards like the feathers on a birdie.

The position is completely counterintuitive.

When you jump out of the plane, your body is telling you to tuck and roll, to brace for impact. But you begin to tumble if you follow that instinct.

In business, and in life, a similar principle applies. Sometimes, the best action is inaction.

You’re always making choices about what you need to do in any given situation, but the truth is, sometimes the best decision is to do nothing at all.

Maybe you want to send an email to an investor who expresses interest in your company or accept a partnership right after receiving an offer. But holding off on major risks can actually be the best thing until you get more information, or can strategically position you in a negotiation.

Our instincts push us toward action, whether it’s in the business world or when we’re falling out of an airplane. It feels counterintuitive to do nothing. But just as you can fall gracefully from an airplane by limiting your body’s natural movements, sometimes in life, it’s better to limit your impulses.

In the end, working methodically and strategically is a better way to take risks than simply reacting to a stimulus.

Success in business and risk-taking always comes from the little things.

When you’re free falling, the smallest movement can have an outsized impact. Just pulling one arm to your chest will send you into a barrel roll. Tuck your head, and you’ll do a front flip.

Business is all about the little things, as well. People like to imagine grand, theatrical meetings that end with massive deals and handshakes, but that’s just not how it works.

Building a business doesn’t happen over the course of an afternoon. It’s the culmination of every little interaction you have with colleagues, partners, and customers.

Something as small as reaching out to check in with a coworker or saying thank you on an email makes an impact. Over time, those are the things that determine your success.

On the other end of the spectrum, negative actions can have an even greater effect. They cause you to tumble without control.

I used to work with an outside agency, for example, and I began to notice the founder had a very negative energy. His language on social media and the culture he was creating involved a lot of bad mouthing other people and their ideas. It rubbed me the wrong way, so much so that I stopped working with them.

There was never a big incident that made me throw my hands up. I just saw these little interactions as something indicative of a larger problem. It wasn’t a risk I wanted our company to take.

You don’t need to have a near death experience to understand risk, but getting out of your comfort zone, putting yourself in risky situations, and learning from the results will help you — and your business — grow in ways you didn’t expect.

Thanks for reading!

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