Chasing failure: A recipe for success

Andy Gold
5 min readDec 15, 2020

“It is hard to fail, but it is worse never to have tried to succeed.” — Theodore Roosevelt

Reflecting on her childhood, Sara recalled that her father had an unusual routine each week at the dinner table. Her dad would ask Sara and her brother to share a story about what they had failed at that week. Her father would then celebrate their failures, and would, in fact be disappointed if his children did not have a story of failure to share. Sara recalls that her dad would “high five” and congratulate her after sharing a failure story. This mindset in turn shaped the way Sara perceived failure. Over the years, Sara began to realize that what her dad had taught her was that failure is not a result, or an outcome. As such, she began to take more action on her imaginative ideas, knowing that if things didn’t turn out as planned, her father would applaud her failure. Because of this upbringing, Sara began to redefine the meaning of failure to simply be…not trying.

It was this mindset, a strong sense of perseverance, and a host of serendipitous events that led Sara Blakely to start Spanx, and became the youngest self-made female billionaire at the age of 41. (

Like Sara, many people have vivid imaginations, and a natural desire to make positive contributions to the world. However, unlike Sara, many people are fearful of acting on their ideas because of how they perceive failure. Entrepreneurship and the creative process associated with it, is one vehicle that allows a person to act on their imaginative ideas. Sir Ken Robinson, a creativity expert, defined creativity as being a form of “applied imagination”. I like this definition for creativity because imagination without a willingness to take action creates nothing, other than good conversation. One must wonder why so many people like talking about their ideas, but so few ever take next steps to further investigate their ideas. While there are many anecdotal explanations for this behavior, this article focuses on the fear of failure as being one of the potential drivers for not acting.

The problem begins in K-12 Education

Young children are wonderful at applied imagination. Societal pressures that shame those that try and fail do not apply to very young people. In fact, we encourage our children to open a lemonade stand, develop artistic skills, and to be imaginative and fanciful. Over time, society begins to change the game of what is expected from a young person. We learn that taking chances can cause embarrassment, and that in turn causes many people to begin learning that failure should be avoided. We learn that getting focused on an employable skill, like engineering, data analytics, science etc. is paramount to pursing creative passions. The result is, that we are creating a large group of young people that are highly educated and relatively unwilling to take chances.

The difficulty with this scenario is that not everyone can be an engineer, or a mathematician, or a scientist, but we are asking, in fact demanding this of many children. This creates a significant problem that may be contributing toward stifling innovation. As many young people track through their education careers, they are nudged from their natural talents and passions, toward academics deemed to be critical for professional success, and, academic disengagement ensues. The result is that many teenagers and young adults lose their creative spirit, become reticent to act, and develop a deep fear of failure. All of these elements stifle innovation and instills a general misunderstanding of what entrepreneurship and innovation actually mean.

Furthermore, many activities that once allowed a K-12 students to apply what they were learning in classes to practice (i.e. shop class, dance, art, music) have largely been stripped away from many schools, or at a minimum degraded. Affluent families are able to provide these activities as a supplement to school by paying for gymnastics, dance, music, and other activities. But what about less fortunate families that lack the financial means to provide this supplement? A recent study conducted by researchers at Stanford, Harvard, MIT, and the U.S. Treasury Department — finds that “children born into the top 1 percent of households by income are 10 times as likely to become inventors as those from below-median income families.” The result is that we are generating an extremely educated population of students that know an immense amount of facts, but hesitant to give things a go. Tony Wagner, an education thought leader, encapsulated the problem with this trend when he said, “Today, knowledge is free. It’s like air; it’s like water… There is no competitive advantage to knowing more than the person next to you. The world does not care what you know. What the world cares about is what you can do with what you know.”

Developing an Entrepreneurial Mindset May Be The First Step Forward

So, how do we train young people to apply what they know? Entrepreneurial activities are one vehicle that enables people to apply not only their imaginations, but also other critical academic skills and subjects, like critical thinking, writing, communicating, engineering, science, finance, and mathematics. The problem is that experiential learning is more difficult to measure on a standardized test. We can begin by saying that most people think of entrepreneurship as having something to do with starting a business. While this is partially true, this is a far too narrow framing for what entrepreneurship actually has become. Compounding this narrow definition is a further narrowing of entrepreneurship primarily among academics, some of which differentiate between a small business enterprise (local business) and an entrepreneurial venture (high growth, scalable venture). Of course, the high growth scalable startups are where most of the attention goes. Entrepreneurship above all else is a mindset; a way of thinking, or a certain set of conventions that promotes taking action. These actions are designed to promote learning and solution searching, coupled with innovations that can add value. This action-oriented mindset is accompanied by a series of intangible skills such having an internal locus of control, a growth mindset, strong sense of self-efficacy, perseverance, adaptability, ability to think big, creativity, resourcefulness, ability to understand and cope with failure in a different light, and problem finding, to name a few.

All these skills are certainly important for a person desiring to start a business, whether it is a small business or high growth entity. But these skills can also be applied to a person who wants to work for, and transform an existing business, or an educator who wants to shape the future for education, or a doctor that wants to develop innovative patient practices, and so on. In fact, developing an entrepreneurial way of thinking can help in so many varied ways. It can help a student excel in school, a municipal worker to develop efficiencies within their scope of work, assist a nonprofit to identify innovative revenue streams, and even change the way government operates. By limiting a young person from experiencing failure, we are blocking a person from learning how to deal with failing, which serves to stifle innovation over time. Share your ideas with me for creating pathways for young people and business leaders to develop cultures that reframe failure as learning, and begin to applaud failure as much as we applaud success.



Andy Gold

A social entrepreneur & community college educator. @profandygold —