Fail Successfully

There was a time when I thought I had life fairly well handled. Both my software and IT businesses were growing swimmingly. I was rapidly paying down my mortgage, and was funneling money into my retirement accounts. On paper, I was doing everything right, but by 2007 cracks started to appear in the IT business. Rather than letting it succeed or fail on its own merits, I drained my bank accounts and retirement savings to keep it alive. By the time the “Great Recession” hit at the end of 2008, clients stopped paying invoices, which brought my financial house to its knees. Despite my best efforts, I was forced to close the office that held both companies, shut down the IT business, and declare bankruptcy — which saw me surrender not only my house and vehicles, but also the majority of my belongings.

Many people over the years have been kind to say that the bankruptcy was not my fault; That, instead, I was just a causally of the recession. However, I could easily find reasons to shame myself: I expanded too quickly; I relied on people who were untrustworthy; I funneled my own money into a business that was not strong enough to stand on its own. Three big business mistakes that perhaps I could have avoided with a little foresight.

The four month period between when I filed Chapter 11 and when my bankruptcy was discharged was one of the most introspective times in my life. It was a struggle to accept the failure that I saw my life becoming. Would anyone want hire me for anything ever again? Would I ever be able to build back up my retirement? Would I qualify for financing again? This experience of failure had me feeling like the life I knew was at a dead end.

One week before my birthday in 2009, I found myself selling the remainder of my possessions in preparation for a move to California. A man walked into my garage sale, looking oddly familiar. He was an ex-bandmate whom I hadn’t seen in 15 years. He literally lived 5 houses away and, amazingly, we never ran across each other! That reunion was both uplifting and bittersweet, since I had already committed to moving. Rekindling our friendship, however, led to me to being introduced to several people on the West coast who are integral to my present success. Had I not gone bankrupt and chosen to move out of state, he and I may never had found each other again, and the life I have created would look dramatically different — and certainly not for the better.

What I learned through this experience is that the dead end I felt so powerfully really pertained only to the old life. In forcing me to let go of that life, my “failure” actually freed me up for something even better. Rather than despise this failure, I came to embrace it for the new opportunities that rose from the ashes.

This is just one of many stories in my life that taught me how a seeming failure can turn into one of our greatest gifts. Today I am immensely grateful for that experience. My perspective has shifted from failure being a foe to failure being a friend. While there are times when I rather it not show up, when it does I know it’s there to redirect me and open my world up to greater possibilities. Like an old friend you can trust to tell you the hard truths, I know it ultimately has my back.

In the past, you may have heard me discuss making things safe as a strategy for moving beyond them. Yet, our mind coding something as “safe” doesn’t always mean that it’s the best experience for us. Sometimes it means we’ve just grown accustomed to our present experience, blinding us to other exciting avenues our lives can take. I learned that there are a lot of ways a person can adjust (or “pivot,” as they love to overuse here in Silicon Valley), and sometimes struggling to avoid a failure is really struggling to avoid growing into some new possibility. With failure as our friend, we can be more free to enjoy life’s up and downs, rather than resenting the struggles and attempting to hold on too tightly to what we think are good times. When we can release the fears and limiting beliefs surrounding failure, we often discover the courage necessary to take the risks that are required to move up to the next level in life.

In what part of your life are you seeing failure as your enemy? What are you most afraid of losing by failing? What might you possibly gain?

“The greatest mistake you can make in life is to be continually fearing you will make one.” – Elbert Hubbard

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