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Successfully Failing

The Paradox of Successfully Failing

A colleague of mine from many years ago affectionately referred to my work style as “fire, aim, repeat” – inferring that I didn’t spend much time in the “ready” phase of the sequence. It’s true. I don’t possess a whole lot of patience for preparation. I’d rather press forward on the best, most clear path forward and then learn from the approach, improving for the next step.

This sequence, which I practiced for more than 20 years, provided me with some wonderfully terrible experiences to draw from. Sometimes I took the hard way around solving a problem. At other times, I was so over prepared for challenges that the (very difficult) work that I did looked effortless. Mostly, however, it helped me to develop some pretty thick skin and a significantly higher risk tolerance than my peers. Not allowing failure to be feared is a freedom few enjoy.


It’s not every day that someone is encouraging the celebration of failure, but there is something to be said for those who have had the honor of a face plant. The more public the face plant, the more victory in eventually elevating after that nosedive. Many people are rooting for the underdog in this world, but that is usually only the case when the underdog demonstrates humility, teachability, and hunger for another opportunity. Understanding that the paradox of successfully failing might just be a pivotal lesson that spurs growth- it is just the thing that helps to build the thick skin required for risk taking.

Risk taking. Yes, risk taking. It’s impossible to talk about successfully failing without starting with an honest assessment of risk. What is there to lose, right? It depends on what a person values. If a person values the appearance of success, risk is scary as hell. If a person values experience, risk is exciting. If a person values financial security, some ventures are not in alignment with that value, and the risk outweighs the reward. Risk taking is dependent upon a clear articulation of values. When the risk is worth the effort, something difficult becomes something that pays off.

Working hard on anything from digging a ditch to training for a marathon undoubtedly brings about blisters. Blister enough, and the skin learns to protect itself by forming calluses. This skin shield may be rougher, tougher, and look a little different, but they sure make a difference in the ability to endure long periods of time in doing hard things. Effort and endurance makes for great calluses. In business, callus making provides the mental toughness to recover from a failure.

Is failure really a bad thing? Not necessarily. If failure is viewed as a deviation from the expected outcome, then it can be categorized in three different lanes: preventable failures, unavoidable failures, and learnable failures. Those preventable failures are great teachers. Preventable failures are also the most embarrassing. To be caught off guard with a preventable failure is usually not an ideal situation, but recovery from a preventable failure can result in new disciplines, innovations, and partnerships. Humility and self-awareness are prerequisites for effectively navigating the recovery from a preventable failure. Unavoidable failures are the least embarrassing…encountering an unavoidable deviation from an expected outcome for some is a badge of honor. When Plan A, Plan B, Plan C and so on are not working, the unavoidable failure is truly unavoidable. There’s no amount of preparation that can prevent this kind of failure. For the risk-averse, this is terrifying. For the entrepreneur, this is life. Navigating an unavoidable failure generates the most sympathy and often leads to innovation on the other side.

The learnable failures are exciting - sometimes the failure is so steep, the lesson learned is life changing. Other learnable failures lead to truly incredible outcomes. Think about all the attempts that Benjamin Franklin made along his inventor journey. The story of electrocuting a turkey for dinner is particularly amusing. Ben had an idea - get a live turkey, zap it with electricity to kill it, and barbeque the dead bird for dinner with the world’s first electric barbeque. Failed attempt after failed attempt, he was nearly ready to quit and had had enough. The sight of the not-yet-dead birds rising from the ashes was scary enough (apparently his shock only knocked the birds out for awhile until he mastered this party trick). Mr. Franklin persisted and he may be personally responsible for the airfryer craze that swept the nation. There aren’t many stories of his failure, because in his persistence, the failures provided him with learning opportunities. Learning failures are infinitely more valuable than any other kind of failure, but also require the most developed calluses.

The endurance of failure should lead to a steadfast and predictable recovery. Recovery, and the return to the risk arena, separates the sideline sitters from the serious goal getters. This is the essence of successfully failing. The real success in a failure is in stepping back after a fail and standing back up after a fall. The thicker the skin, the more reliable the recovery. Throughout my career, I failed more times than I care to count. The failures helped me to define my values more clearly. The failures provided me with proof that boundaries were essential, not superfluous. The failures gave proof that God forgives but nature doesn’t. This last one - it’s a tough one. Some failures are more significant, and require more than an intellectual or spiritual sturdiness. Restitution is sometimes required as part of the recovery process. Some failures must be set right. Restitution is VERY different from retaliation. There’s no success to be found in retaliation. It just perpetuates a failure and extends it. Restitution, however, begins to set right that which was broken by the failure. To swiftly identify when and how restitution is necessary in the wake of failure presents an indicator of a successful failure.

Successfully failing is an art. It is a discipline. It is a decision.

As a master of successfully failing, I have become nearly impenetrable to failure. For that, I have learned to be brave. These failures have provided me with a clarity of intent, a validation of values, and the brawn to defend boundaries. As a leader, a coach, and a human, one of the ways that I continue to fail successfully is through developing powerful partnerships with people who possess qualities that I admire and do not possess in the degree that I would like. As a student of everything and everyone I meet, I am constantly evaluating and categorizing what learning opportunities are in front of me.

Failure may be in the future. It’s certainly in the past.

Preparation presents a peace about Plan A, Plan B, and Plan C. If failure is unavoidable after as many pivots as a person can move through, then growth is already happening. When preventable failures are no longer a possibility, failure isn’t as scary as it used to be.

Bravely approaching the difficult things, especially when failure is unavoidable, is like taking off a pair of steel toed boots and attempting to walk on rocks, glass, or lava – hopeful that the calluses do their job, and ready to nurse the blisters. Innovation has to be around the corner. Don’t give up.

With eyes and ears wide open to learn through the teachable failures, the brave soul may effectively turn a personal difficulty into a professional strength. Demonstrating an excellence in failing is one of the qualities that separates the courageous leader from the safe manager.

Reframing the idea of failure is not easy - and it’s not for everyone. It’s hard work, and this kind of hard work builds a risk tolerance that fuels breakthroughs, innovation, creativity, and authenticity. Again, not for everyone. In order to reframe failures, an individual has to step back and recognize their own limitations. Reframing the idea of failure provides a much needed release of the pressure of perfection. Ask any recovering perfectionist about this release of pressure and the will have a few stories for you. The reframing and the recovery transform a blister into a callus, a bump in the road into a hill that allows a little view at what’s coming next.

Remember this, if nothing else, as the closing words from an exceptionally successful fail-er:
It’s not just about the failing. It’s about recovering from failure.
And becoming immune to the stink of it.

As the founder of a high-impact group for professional women, navigating and reframing life's unavoidable moments is a regular activity. If you are interested in joining Brave Women Project, begin your application process here. If you are looking for a speaker, coach, or consultant to help you navigate successfully failing, click here.

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