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How I Take Risks

Updated: Apr 27, 2022

For many years I envied people who abruptly quit their jobs, start businesses, spend a year traveling the world, invest in start ups, etc.

These people seem to have some unicorn level risk tolerance that I inherently lack.

I grew up chasing safety and security. I fear unpredictability and surprises. This fear has undoubtedly kept me sitting awkwardly at the kids table when I really want to chase big dreams.

So how did I decide to quit my job, take a summer off, and start a new business?

I have Tim Ferris to thank. In his 2006 blog "17 Impossible Questions" he asked:

What are the worst things that could happen? Could I get back here?

I read this blog post about 5 years ago. This question plays ping pong in my head often. I like the question because it feels very tangible. It's a risk mitigation strategy that is pretty simple.

Here's how I applied the question to my decision to quit the corporate world.

1. Worst thing that can happen?

I had to dig into this one. It was not as simple as what if my new business fails. I've done a lot of therapy and coaching over the years and I know myslef pretty well. For me, the worst thing that could happen is not that I fail. It's that I succed.

What???? Yes. It's counterintuitive.

I feared success because I have struggled balancing 4 kids, a farm, my personal wellness, and a full-time job simultaneously. Success may mean that I'm just right back into that cyclone of stress and despair.

2. How can I get back here?