#018: Taking Bolder and Smarter Risks in Business and in Life: An Interview with Riskology.co’s Tyler Tervooren

Summary: In this episode of the Smarter Freelancing podcast, Ed talks to Tyler Tervooren on taking bolder and smarter risks in business and in life.

The biggest breakthroughs I've experienced in my business and personal life have come from taking what seemed to be big risks.

Not the crazy, jumping-off-a-cliff-with-a-wingsuit kind of risk.

I'm talking about stepping far enough outside of my comfort zone that I changed for the better.

Even if the desired outcome never materialized.

If you want to take your freelance business to the next level, you HAVE to start thinking differently about risk.

Risk is a natural part of growth. And they key to getting comfortable with taking more (and smarter) risks is knowing how to do it well.

In today's show, I talk with solopreneur and risk-taking aficionado Tyler Tervooren from Riskology.co

Tyler shares some fascinating information on the art and science of risk taking ... and how we can strategically improve our risk-taking "muscle" as solo professionals.

The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe in iTunes or Stitcher to get this show delivered straight to the Podcasts app on your smart phone, tablet or iPod.

Tell us about yourself and the work you do at Riskology.co

Tyler helps smart people take smarter risks. His website supports people in living more adventurous lives personally and professionally.

What led you to this line of work?

Before launching his website, Tyler worked as a construction manager. Just as he was ready to quit, he was laid off. He launched his website in June 2010. The site started as a hobby but is now becoming a business.

People don’t really talk about risk taking. His business provides an outlet.

What are we talking about when we talk about risk taking?

Risk is an integral part of every day life. We take risks every day. In NOT doing something, we take a risk.

All these decisions about taking risks and not taking risks all add up to who we are and how we live. When we better understand ourselves, we can take decisions that will lead to our best possible lives.

Can you share some of your biggest and most surprising findings?

People chase happiness. In the U.S., we focus on acquiring things and comparing ourselves to others. There’s a saying: The fastest route to unhappiness is to compare yourself to others.

But that’s only partly true. Studies show that social comparison CAN make us feel better if we compare ourselves to those “behind” us, instead of “ahead” of us.

Studies have also shown that men and women take decisions differently when under stress. Men take more risks when under stress. Women take fewer risks under stress. Knowing that difference can help us make better decisions.

How can we get ourselves to do scary, but necessary, things?

Everyone has some idea of where they’d like his or her life to go and how to get there—but the steps seem risky and the award so far away.

A common theme for people who succeed in achieving big goals:

clicktotweetFocus less on the distant goal and more on the small steps needed to get there.

Small steps are easier to quantify and less scary. With each step, you better understand your goal and it looks less scary. You get more familiar with it and start to see the path to get there.

Does everyone need an action plan to take a risk? Or do some people just dive in?

When it comes to starting your own business, some people think, “I’ll quit my job and then figure out how to start a business.” Almost no one succeeds that way.

clicktotweetPeople who successfully start a business begin with an idea, and then test it.

They continue to work their regular job. They develop their idea over time. Once they know they’re headed in the right direction, they can quit their day job.

Name a couple of things you’ve done by stretching outside your comfort zone.

Tyler recently finished the last of seven marathons—running one marathon on every continent. While he’s naturally interested in travel and adventure, he was initially afraid of it. When he thinks back to where he was four years ago and then where he is now, in terms of that goal, he finds it surprising.

Although Tyler’s mostly an introvert, he decided to try online dating a couple of years ago. He set a goal of going on 50 dates as a kind of social experiment. A year ago, he met someone and is now engaged. This is an example of diving into something interesting and getting a wonderful, completely unexpected, outcome.

Is risk taking a muscle? Does stepping out of your comfort zone make it easier to take risks in other aspects of your life?

It’s exactly like a muscle. Research proves it. Your comfort zone is dynamic. When you do something scary, you don’t remain scared of it. Every time you step out of your comfort zone, it gets bigger.

clicktotweetWhen you take risks in one part of your life, it’s easier to take risks in other parts.

Everybody at some point goes through a period where it feels like everything is in shambles. It can seem overwhelming to get things back on track. But you don’t have to fix everything at one. You can pick one thing, and as you work on it, it improves your motivation and ability to improve the others.

If someone wants to make the leap to freelancing or wants to take his/her business to the next level, how should they start?

Don’t focus so much on the outcome. You don’t have to take one big risk. It’s a series of many small risks. Use the outcome as a guide for what you need to every day or week.

When you take the smaller risks, it builds momentum and makes it easier to reach the bigger goals.

Where can listeners learn more about you?

Tyler’s website: http://riskology.co


  • Great talk Ed. I haven't given it much thought but anyone looking in from the outside would consider me an extreme risk-taker I suppose. I've been to 45 countries, flew to Antigua hoping to get work on a yacht and ended up building the 1st cellphone company in the Caribbean. Etc, etc..

    But my experience is the older I get I'm less and less willing to take risks. And it shows in my business. I'm guessing but I think this may be a common experience.

    So I threw caution to the wind, got my hands on some money and am going to AWAI's BootCamp in a couple of weeks. While listening to your talk it occurred to me that this decision was a major risk. A calculated risk mind you, but a risk nonetheless.

    Looking forward to seeing you in Delray Beach Ed. I'll save a chair for you so we can continue this discussion. 🙂

    • edgandia

      You bring up some great points, David. I think our risk-taking varies from role to role. And I agree that the risk-taking muscle can atrophy with age. I'm no expert, but I've found that gradually exploring and taking smart chances in ANY area of our life will impact the other areas. I've seen it happen over and over again. So maybe try doing a few things that feel scary (but you know are also good for you). You might surprise yourself. (Sounds like the Bootcamp decision might be a great start!)

      Great to hear you'll be in Delray. Let's definitely meet up there. 🙂