A Risk Averse Life

All endeavors in life involve some element of risk. But if you are living a risk averse life, you are probably not living the life that you want and deserve.

I have always wanted to be an entrepreneur and self-employed. For me, it was always about creating something, adding value, and my own personal freedom more than it ever was about money.

In 1997, I started my first company, Sweetwood Information Services. And to be honest I had a great start, awesome plans and ideas, and a lot of excitement. But it never really left the ground like I wanted it to. There are many reasons that I can point out but the number one reason was that I was still to risk averse to commit 100%. There were bills to pay, responsibilities, and other factors that I was beholden to which made making that leap of faith just way to darn scary to take.

I started another company 15 years later that was a partnership. Again, we had great ideas, we were excited, and I believe we had an awesome product to offer to clients. We also had a way-too-safe plan for both of us to exit our day jobs in order to work exclusively on building that business. We were too comfortable where we were, we were not hungry enough to take the risks, and in the end, everything stalled. Same story as before, both of us were too risk averse for too many reasons to be able to cut the cords that bound us and to go for it.

With both of my first companies, if I really wanted to make that change I would have taken the actions needed without rationalizing why. Instead, I spent my time and energy rationalizing why I should make the change before jumping into the unknown. People ready to make great changes in their lives make the change, then rationalize why they made the change, and not the other way around as I had done. No matter how you color it, I was still to risk averse.

So how did I manage to make this transition to full-time self-employment? Did the stars magically align making everything simple and risk free? No… they lined up a little and presented me with the opportunity to follow a new path if I chose to, but there was and is still significant risk… even two years later, there is still risk.

I never saw myself as being averse to success but looking back now, I can see how my aversion to risk was always a limiting factor in my life. What changed? The short answer is that my life hitting a tipping point.

I was fed up… fed up with corporate politics, policies, and all of the frustrations that came with that. I was tired of stress and the day-to-day tasks of the job that no amount of money that they might reasonably offer me could satisfy me. I was tired of feeling my soul die a little bit each day. And now in retrospect I can see that the greatest joy-killer in my life was that I knew down deep in my heart that I was not making a difference in the world by just working and getting a paycheck. I was not making a difference and making a difference and helping people is now my number one focus in life and what I strive to do everyday.

Helping others, either though writing or working with clients one-on-one is my passion and it is also my business, and I have never been happier in my life.

The move to Aspen was inevitable in my life, and I was ready to take all the risks. But what if I failed? But what if it all didn’t work out? The metaphor is crude, but my mantra then became, “So what! I’d rather shovel shit in Aspen than to eat shit in Colorado Springs.” Now if that doesn’t show you how dissatisfied with the status-quo in my life and illustrate how motivated I was to make a change, I don’t know what will.

My heart goes out to everyone who still struggles around risk aversion and who lack the courage to strike out on his or her own and to do what he or she really want to do in life. I can empathize because that was my own personal plight for over 20 years. I know what it’s like to stay in the comfort zone, doing meaningless work day after day. I’ve been there; I know what it is like to know what you really want and still find excuse after excuse to stay put.

This has been the greatest risk of my life but I can also tell you that I have never felt more successful, more alive, more relevant, and more purposeful ever. And all of those things put together makes me one happy-camper. Because I finally stood up, decided to take the risk, everyday my life is a success.

Somewhere I read that one of the biggest regrets that people have later in life is that they didn’t have the courage to live the life they wanted to live verses following society’s path of expectations and normalcy. I believe what changed everything for me and empowered me to choose to no longer be risk averse was that I did not want to risk that… to be old and looking back and saying, “I wonder…”

If you are risk averse, I ask you this… from which perspective would you rather look back on your life from, 20,30, or 40 years from now? If you are going to risk anything in life, I will always advocate risking for your success, rather than risking for later regret. Which will you choose?

What are you waiting for?

Andy Wooten M.A. Counseling – Certified Life Coach – Aspen, Colorado


  1. […] to not taking risks. All endeavors in life involve some element of risk. But if you are living a risk averse life, you are probably not living the life that you want and […]

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