top of page

The Reasons I Aim for Failure in Business

I have heard a lot of business experts echoing the statement, “Failure to plan is planning to fail.” While I can’t argue that planning is a vital (often overlooked) step in growing a business, I also know that the best-laid plans can fail horribly just as often. Failure is a pervasive force.

In my 25 years of owning and running small businesses, I have found that it is entirely possible to haphazardly trip into our success without planning, and just as possible to fail when our plans are meticulously designed and executed. That’s why I actually try to fail.

The Need for Failure

Failure is our greatest teacher. We are taught from childhood that failure is both painful and avoidable. We then spend the rest of our lives trying to avoid failure as if it were the Grim Reaper.

Regardless, we still fail. And we do so often. Some failures have major impact, such as business bankruptcy, divorce, incarceration and physical trauma. Others are mere blips, with the result of fees, scraped knees, or a lost opportunity.

The common thread in all these failures, both large and small, is that we are still alive, and as long as we are alive, we have the opportunity to change, learn and grow. Failures teach us valuable lessons about ourselves. We come to know our strength, our resiliency, our beliefs, our blind spots, and our true desires.

Failures teach us valuable lessons about ourselves, our strength, our resiliency, our beliefs, our blind spots, and our true desires.

I am eternally grateful for the failures I have experienced in business, such as learning that a particular business partnership was a terrible fit. Underneath the decision to enter into that relationship was the belief that I was not capable of what needed to be done. When the partnership dissolved, I was still standing tall. I realized then that I was absolutely capable after all. I would not have truly understood that lesson without having failed in the partnership.

I also am grateful for the lesson of failure from my staff bookkeeper and office manager. She stole my identity, racking up tens of thousands of dollars in forged credit card debt in a 30-day period. By the time that happened I had to spend a tremendous amount of time uncovering all the breaches, dealing with the police investigation, locking down my identity, and at the same time, running my business.

The reason I failed to secure my financial safety was because I felt I could not afford the time to stay informed. Misplaced trust was born out of a deep sense of overwhelm. As a result I spent even more time cleaning up the mess that never should have happened. I learned that when it is critical, I can make the time. Busy is its own brand of failure.

Looking for Opportunities to Fail

Failure hurts. Why would anyone go looking for it?

Because I know I must not fail to learn, I have learned it is necessary to fail. Otherwise I am coasting. If I’m not actively trying to fail, I am just playing it safe, and the irony is, failure will find me anyway – real failure. Real failure means to never quite live a deeply meaningful and satisfying life. Real failure is to hide, avoid and try to escape from life in order to escape from ever failing at anything.

I know I cannot manage failure. I cannot plan it away. I cannot save it away. I cannot love it away. I cannot do an affirmative prayer and stop myself from having the experience of failure. Failure will find me, if I don’t find it first. (Of course, we can discuss the semantics of whether what we call failure is really failure after all. But if it feels disappointing, painful and raw to us, then let’s just own that it feels like failure and move on. )

So what I have learned to do is to fail fast. I recently heard several people refer to the phrase, “If you’re not failing, you’re not moving fast enough.” Trusting in the intuitive idea enough to commit, and move 100% in the direction that commitment dictates requires full engagement. It also requires risk. I am not an adrenaline junkie, but I know how to put a full plan into action in days and weeks, where many businesses can take months or even years.

The longer and slower the climb, I believe, the faster and more painful the fall. Markets crash, economies implode, customer demographics and trends come and go. We can foresee some of it, but we cannot foresee all of it. Therefore, we must plan to fail.

What planning to fail looks like is an acceptance that there are going to be curve balls. We must always be already working on the next action even as we are rapidly engaging the first idea. This is what real juggling looks like.

As a practical example, I launched my new business last year with the intention to break onto the speaker circuit and build a career as an author. What I found was that while this plan is not unrealistic, it does take time to build a following and establish the credibility required for higher volume sales. My plan for immediate sales stalled. I failed.

But by this time, I had learned about failure. I was ready. I had the offering of business coaching and marketing consultancy in place. As a result, my entire business was not a failure, even though one component failed to launch as planned. I planned to fail, and as a result, my pain was not so great, even though my learning was keen.

I am still cultivating my speaking and writing, even while I am coaching and consulting. My entire launch, fail, learn, pivot timeframe was 90 days. I failed fast and kept moving. Think about all the wildly successful business people who have a trail of major failures in their wake! Thomas Edison, Elon Musk, Oprah Winfrey, Richard Branson, Walt Disney, Arthur Blank – the list goes on and on.

Why would anyone expect they would succeed on the first round? No bumps? No bruises? How unrealistic! The trick isn’t to succeed at first. The trick is to realize you must be in this for the long haul, and keep going.

The Failure Failsafe

There are two distinct meanings to the word “failsafe”. Most people prefer the definition “to prevent any malfunction whatsoever”. The definition I am using here is: “causing a mechanism to revert to a safe condition in the event of a malfunction.” I believe an open appreciation of the benefits of failure – including its miraculous ability to bring our businesses back to operating in a safe condition even in the event of a malfunction – is the most optimistic approach possible. Failure demands we adapt and transform. Why resist?

There is a dangerous idea being floated out there in some circles that if we experience failures it is because our mindset is somehow wrong. The belief behind this is that although we are optimistic on the surface, underneath, in our subconscious mind, we are holding sabotaging beliefs and creating our own failure subtly. For the individuals adopting this stance, failure becomes a rich opportunity for self-recrimination, deep soul searching, and many attempts to find out where they went wrong. What is they didn’t go wrong at all? What if failure is just part of the life affirming process itself?

I am a believer that how I choose to think does indeed create my personal experience. But my personal experience is my own attitudes and responses to what occurs around me. I delight in embracing failure as natural and normal, just like the change of seasons, the aging process, and chaos theory. I expect it. I don’t resist it. As a result, my business mechanism return to a safe condition quickly, so I can learn what needs to be learned and move on.


There’s a lot of good work to do. No need to let a little thing like failure stand in the way.

2 views0 comments


bottom of page