Summer Series 3: In the spirit of meaning-making, let’s revise the meaning of failure.
June 29, 2023
It’s trendy in educational circles to talk about “embracing the learning experience of failure” or “teaching students to not fear failure,” but at the end of the day, it’s the same old story: we’re afraid. When we do a cost-benefit analysis, we tend to overload the cost side and assume it is not worth the risk. When we consider our shareholders, our customers, and our employees, we decide to play it safe and minimize damage. Playing it safe can certainly be appealing—especially in the independent school arena. When the school board looks at enrollment numbers and makes a direct comparison to customer satisfaction in the classroom, it can be enticing to continue to rely on tested methods of the past. It can be enticing to avoid failure at all costs. It can be enticing to stay comfortable.
But comfort is the enemy of progress. Consider one of the greatest “failures” in Greek mythology: the flight of Icarus. Joined by his father, Daedalus, Icarus donned feathered wings to escape the labyrinth. He was instructed to avoid flying too close to the sun lest the heat melts the wax adhering the feathers to his body. This advice was well and good, but Icarus, once aloft and under the intoxicating influence of flight, tests the boundaries and, inevitably, flies too close to the sun. The wax melts and he falls to the sea to meet his drowning fate.
Alas, we say, Icarus fell. Icarus disobeyed. Icarus failed.
Except we are forgetting one key fact—Icarus flew. Icarus soared above the clouds and touched the very fabric of the heavens. Who among us can say the same about ourselves? Who among us would have stayed in the labyrinth for fear of potential failure?
The speaker in Jack Gilbert’s poem, “Failing and Flying,” draws attention to this fact and then compares Icarus falling to a marriage failing. People focus on the pain of the divorce instead of the beauty of the love that preceded it. People focus on the fall and forget all about the flight. People say Icarus failed and ignore his reaching for glory. Of this, the speaker states, “But anything worth doing is worth doing badly . . . How can they say the marriage failed?” Indeed, how can anything be labeled a failure if it merely came at the end of an attempt at greatness? Gilbert’s poem concludes with the following lines: “I believe Icarus was not failing as he fell, but just coming to the end of his triumph.”
This sort of thinking requires an inherent redefining of the word “failure” itself. Consider the following: as children, we are instructed through both literal words and powerful actions that failure is bad. We are taught that to fail is to not succeed and that one does not want to fail, therefore one wants to ensure success. The best way to ensure success is not to try in the first place. This thinking is deeply ingrained in us and, over time, becomes the emotional response that unconsciously accompanies the very mention of the word “failure.” No matter how many times, later in life, we may be told that failure is, in fact, good and should be celebrated, we are unable to get past the emotional underpinning of “failure is bad.” If we dig down, we discover a logical syllogism:
Failure is not succeeding, and failure is bad; therefore, not succeeding is bad.
This is the state of things. Try as we might, we cannot overcome decades of indoctrination to convince ourselves that failure is actually good. Trust me, I’ve tried. No one wants to jump up and down in celebration of failure. It is, as it has always been asserted, bad. The easier approach, and the approach more likely to stick, is to redefine the word “failure” itself. Keep the negative emotional response with the word “failure” and change the definition to “not trying in the first place”:
Failure is not trying in the first place, and failure is bad; therefore, not trying in the first place is bad.
In the end, we’re not going to convince an entire population that failure is a good thing, and although it may be overly optimistic to think that we can convince them to redefine the word, redefining—an act that lives in the intellect—is easier than overhauling an emotional response—which lives in the heart and in the gut. It is especially possible if we begin the approach when our students are young.
Sara Blakely—American businesswoman, philanthropist, and founder of Spanx—shares in her Masterclass on Entrepreneurship how her father, around the dinner table, would regularly ask the family what they failed in that week. Did they try out for something that didn’t work? Did they make an attempt that turned into a disaster? If they had nothing to share, he would be visibly upset. What Blakely realized, years and years later, was that he had been reconditioning them to think of failure differently. He had been subtly altering the intrinsic definition of the word to mean “not trying in the first place.” He had been helping them realize that what she should avoid is the regret that comes from missed opportunities.
Armed with this definition, we now avoid failure by trying or attempting. We must avoid, at all costs, not trying in the first place. Not trying in the first place is the breeding ground of regret—a sentiment shared by journalist Sydney J. Harris who stated, “Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable.” Consider your own history—are the heartstrings of regret pulled more at the things you tried without success or at the things you never tried in the first place? By altering the very definition of failure, we are offering our teachers and our students the opportunity to live a life free from inconsolable regret.
We, as educators, have considerable power at our disposal. Ours is truly a noble calling—we are given the opportunity to influence the mindset of future generations. It is up to us to give them the tools they will need to succeed in an ever-changing world—as disruption strikes and industries collapse, our students will be at a severe disadvantage if they define failure traditionally and fear the concept itself. By altering one of these aspects, we give them not only hope but an ability to thrive in the uncertainty, an unshakeable willingness to make attempt after attempt after attempt on the path to success. This also means, however, that we become willing to release our hold on results and outcomes as the sole measures for success. Our focus must shift to the process—try, not succeed, try, not succeed, try, succeed—rather than a desired outcome based on a time restraint. This is, in short, a mindset shift within our entire educational culture–we get the results that we measure, and if we shift what we measure, the results will follow.
In 1993, David Bayles and Ted Orland published a book titled, Art and Fear: Observations on the Perils (And Rewards) of Artmaking. They told the story of an art teacher who wondered what would happen if he experimented with his assessment method. As a side note, consider the power (and it is powerful) of a teacher who wonders what would happen if. Imagine the potential of asking not only “What if?” but also “Why not?” This teacher divided the room in half and assigned the first half to a quantity assessment and the second half to a quality assessment. The quantity side had to turn in fifty ceramic pots (any quality pot, even an atrocious one, was acceptable) to get an A while the quality side had only to turn in one perfect pot to get an A. At the end of the semester, the best works were turned in by the quantity group. Turns out, in working at something over and over, making attempt after attempt, a sort of refining process happens that yields a better result. Turns out, true failure has nothing to do with success and is rather the refusal to make attempt after attempt after attempt.
The impacts of this style of thinking on education are endless. Redefining failure is a key attribute of what is referred to as the entrepreneurial mindset. In enabling our teachers, and our students, to think like entrepreneurs—to ask, “What if?” and “Why not?”—we are giving them a path to success. A bumpy and misshapen path, for sure, but a path nonetheless where the learning yields not only rewards but a life free of inconsolable regret.
Stephen Carter is the Director of Entrepreneurship and Sustainability at Cincinnati Hills Christian Academy where he has taught for 17 years. His forthcoming book, Teaching the Entrepreneurial Mindset, chronicles the ten-year journey of the entrepreneurship program and his own experience in learning to think like an entrepreneur. He is available for speaking and consulting and can be reached at [email protected].

