Have You Failed Yet This Month?

Have You Failed Yet This Month?

Stephen Carter
December 4, 2023
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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? Poet Jack Gilbert reflects on this concept when he states, “I believe Icarus was not failing as he fell, but just coming to the end of his triumph.”

This kind of thinking is in line with self-made billionaire entrepreneur Sara Blakely who explains that true failure is “not trying in the first place.”

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.

Want to Learn More About Redefining Failure? Listen to the Podcast for the Full Explanation


Icarus Also Flew - It’s Important that We Redefine Failure


Spaces are Filling Up for the CHCA Entrepreneurship Symposium

Register now for…

The CHCA Entrepreneurship Symposium, March 7-8, 2024, at Cincinnati Hills Christian Academy

Two Days of Value-Packed Content alongside Real-world Examples from our Ten Years of Entrepreneurship Programming.

Attendees will

  • -See multiple student-run businesses first-hand including a fully-equipped coffee bar, a greenhouse business, a wood-fired pizza oven, and a video production team
  • -Obtain curricular outlines and plans to start or enhance entrepreneurship programming
  • -Spend two days with Stephen Carter, program director, author, speaker, and consultant whose mission is to develop the entrepreneurial mindset in all learners.
  • -Learn the inner-workings of a nationally recognized entrepreneurship program complete with six student-run businesses, 15 elective courses, and a certificate track.
  • -Hear from highly influential speakers on entrepreneurship education
  • -Receive enormous value-add for your school

Who this is for:

  • -Schools who want to engage students in a meaningful, Christ-centered way with real-world practical skills for success
  • -Schools who want to begin to develop alternative revenue streams to become less tuition-dependent
  • -Schools who are focused on growth both internally and externally

Who should attend:

  • -Heads of school
  • -Upper school principals
  • -Curriculum directors
  • -Innovation directors
  • -Lead teachers of 7th-12th grade
  • -Passionate Educators

Pricing: $495 for one attendee, $1,200 for three attendees from the same school


Imagine your culture infused with growth mindset, grit, redefining failure, and opportunity seeking. Imagine your team acting and thinking like entrepreneurs.

Stephen Carter

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