Fail Your Way to Freedom

Failure. I’m actually pretty good at it.

As I reflect on my life, there’s a respectable list of stuff I’ve failed at.

  • First marriage ended in divorce (first of the many grandchildren in my family to get divorced).
  • Been broke and deeply in debt several times.
  • Fired from a couple jobs.
  • Failed friends in the moments when they most needed me. One could have had tragic consequences and only didn’t by luck.
  • Two failed efforts at building my own businesses.
  • Declared sterile by a Doctor prior to having kids (this may not be a failure by some definitions, but it sure felt that way to me).
  • Lost every student body election I entered in high school and college
  • First job out of college was…wait for it…delivering pizzas.

The list goes on. These are just some of the more memorable ones. I don’t mean to start some sort of failures comparison game. Nobody wins that one.

I started reflecting on this list because of some recent article I stumbled across espousing the value of learning from failure. It was one of the thousand articles out there proclaiming that failure is all about learning.

I agree that failure is a great teacher (if you are paying attention). I feel better equipped to be both a husband and an entrepreneur today because of my past failures.

But I don’t think that the most valuable thing in failure is learning. It’s surviving.

People often marvel at the fact that I am “out on my own” in business (translated, this means without a steady paycheck and company-sponsored health insurance). And, then I blow their minds by sharing that my wife works with me. We (and by extension our whole family) are out on this limb together–no safety net.

This sounds terrifying to most people.

Not to us. What’s the worst that could happen?

The business could fail. Been there, done that. 

We could end up broke. Yep. Done that too. Made more money and dug out.

Our family could have to start over or make big changes in our lives.  Maybe so. Wouldn’t be the first time.  

When you survive failure and make it to the other side, you realize something almost magical. Failure isn’t fatal. In fact, it’s almost never as bad as you expect. And, there’s always more opportunity on the other side if you just keep going.

The gift in failure is realizing that failure is just part of the process. It’s about making risk feel, well, less risky. Sometimes, when you take a chance or make a moonshot, you are going to fail. Other times, you won’t. You will create or find something amazing. You will seize an opportunity you may have thought beyond your reach.

Fail enough to take the fear out of risk and a whole new world of opportunity reveals itself. No longer does walking away from a job you hate or leaving a dysfunctional relationship or speaking your uncomfortable truth out loud feel so scary.

Surviving failure sets you free.

Take more risks. Fail more often. Find your freedom.



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