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Using Chaos & Failure to Cultivate Entrepreneurial Resilience

Face it, the road to entrepreneurial success is one filled with obstacles. From potholes to unexpected bridge closures, to bumper-to-bumper traffic... occasionally even the fuel gets low as you search for the metaphorical gas station for an energy and optimism refill. However, you are an entrepreneur, and you would not have started your business if you did not already have a resilient nature.

Image: Arrows pointing to image of human head with resilience written over the brain

Psychology Today says that resilience is the psychological quality that allows some people to be knocked down by the adversities of life and come back at least as strong as before. Rather than letting difficulties, traumatic events, or failure overcome them and drain their resolve, highly resilient people find a way to change course, emotionally heal, and continue moving toward their goals. (

Resilient entrepreneurs calibrate. They willingly and consciously take risks. They see answers and opportunities in problems. Their comfort zone is in embracing being uncomfortable. They know failure is a possibility, and even welcome the growth and lessons that come with it. They know fear is powerful, and they know it is intended to protect you. As leaders, they also know that the bubble of protection offered by fear, no matter how tempting, is built on the foundation of safe limitation. Ok, we have clearly established that being an entrepreneur requires resilience. So how can we, as entrepreneurs use chaos and failure to cultivate and strengthen our resilience?

Failing Forward

I have been accused of being a perpetual optimist, of wearing rose-colored glasses... yes, I have even been called Pollyanna. What may have been intended as mocking earlier in my career, turned out to be a cornerstone to building resilience. Even if I didn't know it at the time.

My thought was always that it was better to move forward than to stand still. Welcoming potential failure, and its accompanying lesson. Knowing that I could always calibrate. I only had to start.

According to data from the U.S. Bureau of Labor Statistics, about 20% of U.S. small businesses fail within the first year. By the end of their fifth year, roughly 50% have faltered. After 10 years, only around a third of businesses have survived. Lisa M. Amos noted, "Entrepreneurs average 3.8 failures before final success."

“Success is not final; Failure is not fatal; it’s the courage to continue that counts.” -Winston Churchill

Resilient people not only embrace failure, but also the accompanying vulnerability. Unbroken success does not test us, nor does it grow us. The required emotional intelligence for building resilience tells us that we must reach out and reach up, that vulnerability is as powerful as fear, and defeat is only momentary.

But how does failing build resilience, really? In the Art of War, Sun Tzu said that "Sometimes we need to lose the small battles in order to win the war." Face it, we can not always win. Business resilience, mental resilience, emotional fitness... whatever we want to call it, requires us to embrace the failure - not as defeat - defeat does not serve us. Instead, we must embrace it as training. As a key factor in exercising our problem-solving skills and as an opportunity to rest in and learn from. Even the uncomfortable emotions that come with failure, and the associated growth.

It is not the failure itself that builds resilience. It is the intentional decision to risk failure, accept failure, and walk in friendship with failure as your coach and trainer.

Cultivation through Chaos

Image: Sign that says Keep Moving Forward

The year 2020 has been an absolute tornado of chaos. With the current pandemic and associated challenging situations. It has been nothing but ongoing change and adaptation. Many have faced difficult experiences, from unemployment to juggling homeschooling with working from home, and for some, loss. The impacts on mental health are sure to be studied for many years to come. Even the most resilient individuals were forced to take a pause and evaluate what seemed to be an ever-changing landscape of what was once their “normal” and make adjustments.

“In the midst of chaos, there is also opportunity -Sun Tzu

As Sun Tsu noted in The Art of War, there is opportunity in chaos. This does not mean that one need be “opportunistic.” Opportunity can refer to new ways to serve clients. For example, I have reworked my strategic planning process to be fully functional, and even better remotely delivered service. It can mean leaning in or changing focus in your business. And yes, the “opportunity” can even be flexing and strengthening your resilience.

Stress and chaos go hand in hand. This stress is engaging the prefrontal cortex and strengthening our “neuroflexibility.” (