“They Fail to Fail Enough Times”

Why So Many “A” Students Fail When it Comes to Success

Author

Stephen Carter
July 27, 2026

There is certainly a spectrum when it comes to reading about money and financial management. On one end, we have Dave Ramsey and the conservative approach to getting out of debt and living within one’s means. On the other hand, we have Robert Kiyosaki, who advocates leveraging debt to build assets.

I’ve always found the best approach to be somewhere in the middle of these two leading voices, but I still enjoy reading what each of them puts out. Recently, I’ve been re-reading some Robert Kiyosaki—specifically his work on Cashflow Quadrant, where he advocates for readers to step out of the “employee” quadrant and into the business owner and/or investor quadrant.

The book itself contains some great concepts, but I was especially drawn to his thoughts on failure.

Early in the book, he states, “so many ‘A’ students get stuck in ‘analysis paralysis,’ studying every little detail, but failing to do anything.” He goes on to explain that this “analysis paralysis” is “caused by our educational system punishing students for making mistakes” and argues that ‘A’ students “simply made the fewest mistakes.”

Truer words would be hard to find.

Our educational system is designed to keep students in line, following a rubric and a detailed map to a destination which, unfortunately, no longer brings the promise it once did. Students learn to search for the correct answer, avoid unnecessary risk, and protect their grades. Then we send them into a world where the path is unclear, the rubric is missing, and progress often depends on their willingness to act before they have every answer.

If we are not encouraging our students to make mistakes and to experience failure, we are not actually preparing them for the real world.

Kiyosaki goes on to say, “The reason so many people fail to achieve success is because they fail to fail enough times.”

That statement alone should be enough to warrant every school around the nation starting an entrepreneurship program and outright encouraging students to fail. To fail over and over and over—and then to fail again—until they understand the primary role that failure plays on the path to success.

Success is a poor teacher. We learn very little from it. Failure, on the other hand, is a wonderful teacher. Although the lesson is often painful, it can be highly instrumental in shaping our journey toward success.

John Maxwell touches on this in his work, Failing Forward. Toward the beginning of the book, Maxwell argues, “many people are training for success when they should be training for failure.”

Imagine that: training for failure.

If schools were to embrace this revolutionary concept, we would do a world of good for our students. No longer would students enter the world unprepared for the volatility and uncertainty that grow daily. Instead, they would go armed with a mindset of resilience, knowing that inevitable failure is not the end of the journey but a building block on the route to success.

That is one of the great powers of entrepreneurship education.

Your entrepreneurship program is essentially a failure laboratory. It gives students a place to take risks, test ideas, make mistakes, receive feedback, adjust, and try again while the stakes are still relatively low. It is in this laboratory that learning comes alive—and where students develop the resilience they will need long after they leave the classroom.

The goal is not to teach students to enjoy failure. The goal is to teach them not to fear it.

Because the students who eventually succeed may not be the ones who made the fewest mistakes; they may simply be the ones who were willing to fail enough times.

Interested in building this kind of learning environment for your students? Reach out to learn how Seed Tree Group can help your school develop an entrepreneurship program where students learn to take risks, create value, and fail forward.

Standing out as a Christian school while staying true to your values is more challenging than ever. At Seed Tree Group, we help schools implement a proven entrepreneurship program that empowers students to take ownership of their education, equipping them with life-ready skills and creating a distinguished school with engaged students, inspired parents, and energized donors.

❝

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

Stephen Carter