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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?

I beleived that if my business succeeded I would have to work at it forever. No matter what.

This is the juicy turnaround.

Who says you can't change something that is successful?

Other people. Other people say that. Guess what? Those people aren't living my life. I am.

So I decided that I would remain in control of the amount of work I wanted to engage in at all times. How? Boundaries. My boundaries are that at all stages of the business I will:

- Work only Tuesday- Thursday

- I will charge a market rate from day one

- I will engage in some fun part time paid work now to take the pressure off of selling

Boundaries my friends.

Let's play devil's advocate though- what if it all fails? What if my hippie approach does not work out?

Then I change it. Simple. I weigh my options when I get there. Which could look like going back into the corporate workforce, working with start ups, or running a non profit, etc. Who knows?? There's so many fun and exciting things in the world. Why can't I have an open mind about all of them?

In that exercise what I realize is that I have an infinite ability to make money. I can expand and explore all things. The path need not be linear.

Oh one more thing-- taking risks may require you to not give a shit about what others think. But this is truly a blessing.

Thanks Tim Ferriss, I appreciate the mind shift.

If you want help working through a tough decision, I can help. I have many tools in the box that can help us get you where you want to be.

Schedule a free consultation call to learn more about coaching with me:

In Happiness & Health,


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