Handling risk - or, what I learned from hurtling down a hill at 45 miles an hour in my underwear with no brakes

When I was a full-time athlete (a long distance inline skater), I took a lot of risks. In races, we often skated down steep paved hills at 40 to 50 miles an hour in just a spandex skinsuit with no protection except a helmet. I thought this made me a risk-taker by nature and that I would take that same approach in business, and that it would be fine and I would rock it.

I found this was not automatically the case.

In sports, the risks are physical, and when you screw up, there’s no mistaking it. You fall, or a referee calls foul, or the ball goes through your hands, or the other person goes over the line first. You deal with it, learn from it if you can, and keep moving.

However, entrepreneurship requires taking a different kind of risk: social risks. If there is harm, it comes to your reputation, your ego, your power status, your relationships. On these goals, you don't get clear, immediate feedback – if you are failing to flourish, it is not easy to find out why.

Therefore, it’s easy to be consistently anxious about how you are doing, whether you are doing the right things, and what people REALLY think. The anxiety can really get you: what if I missed an obvious, important point or perspective? What if I showed my inexperience? What if I am tone deaf?

That’s where it got me, at least. And I found myself becoming so cautious that my anxiety about taking social risks was really holding me back - second guessing myself, wasting time endlessly checking, and keeping me from putting myself out there and going after opportunities to do work I loved and knew I was good at. If you don’t take any risks, you can’t reap any rewards.

Luckily, when I backed off and thought about, I realized there were some ways I could manage the social risks that scared me, in ways that made them more like the physical risks that didn’t.

Here are five ways to make social risks easier to handle:  

1) Think through the rewards of doing the scary thing. Don’t do it just to be a badass. But if you find there’s something scary standing between you and something you really want, don’t go through backflips to pretend you don’t want it. Just decide to practice, learn, and get good enough at it that it becomes a small obstacle instead of a large one.

2) Think through the risks. What is the outcome you are worried about? And realistically, how likely is it? What can you do to lower the probability of it happening? For example, in skating, we might worry about falling on the superfast downhill part of the course, where a fall might mean a broken bone or worse. But that’s not the whole race! That’s just 30 seconds of the race. It is actually less likely that we’ll fall on the big downhill, when we are really paying attention, than on the rest of the course when we are tired and distracted. Those falls aren’t great, but at least they aren’t lethal. So we can train for the scary part - the more skills we have, the lower the risk - but not to the exclusion of everything else that we need to do to get a good outcome.

3) Know the difference between a big risk and a little risk

Most of the things that scare us aren’t really that dangerous, once we think them through. If there’s a big payoff, it pays to decide to start learning how to tackle these every day so they become no big deal. but also visualize the process of getting through it all right, in great detail, start to finish. Visualization is almost as good as real practice and will help you manage your emotions.

4) Find your support network.

When I was skating, I knew that if I turned into a pavement pizza, I could get help. Someone would help me get patched up, and get back out there again. It’s harder with social risks: depending on our earlier experiences, we can feel like if we make a mistake, we’ll be in it alone with no one to help. How to combat this? Cultivate friends who like you for you, and also have some knowledge of what you’re up to. Ask them for honest feedback. Have them with you (or symbolically, with a picture) when you have to do something scary.

5) Think through how to recover if you screw up.

In skating, we used to practice falling on purpose, so if a fall became inevitable, we could do it without hurting ourselves too much and get back in the race. Now, for social risks, I make an if/then plan – for example, if I say something stupid on social media, I will apologize and/or follow it up with a joke that someone from my support system friend has ratified.

Sports taught me that taking risks was not just okay, but the only way to excel. Physically safe? Maybe not. But the sports mentality has given me a good model for analyzing the risks that scare me in my business pursuits. Now when it’s time to take risks, I try to remember these five lessons and get through it with a smile.