How I Teach My Students to Fail Forward

“The world comes into our consciousness in the form of a map already drawn, a story already told, a hypothesis, a construction of our own making.” –Rosamund Stone Zander and Benjamin Zander, The Art of Possibility

Last week in staff professional development, an amazing art teacher in my school leaned over during a transition and whispered to me, “You are writing a book, right? This needs to be in it.” He then slid a little yellow book stuffed with margin notes and post-its to me. Its cover read The Art of Possibility.

During the mid-morning break I opened it, and I was so instantly hooked that by the end of the day, I’d used every spare minute, break, and transition to devour nearly half of it. By the time the day ended, the book was done and my mind was already thinking about how to work it into my classroom this year.

When I reflect on why the book had such a hold on me, I think part of it was the intersection of its remarkably positive message with the optimist dawn of a fresh school year. The book is awash with anecdotes reminding us that while judgment and jealousy come easy, in general we find more success when we search for people’s strengths, not their failings, and find places to contribute instead of fixating on areas where we have been overlooked. But, as I think on it now, while those messages were nice, what really grabbed me about the book is that it offered a potential answer to a problem that I have been grappling for some time:

How can I help my students to view mistakes, missteps, and failures as potential positives that can teach them essential lessons?

If I’m being honest, even as an adult who has read more than a few pieces about “failing forward” and the importance of failure, I find myself regularly avoiding situations where failure is likely and brooding more often than I’d like when I make mistakes. And if I feel that way, how can I hope to convince my students–many of whom have been thoroughly trained that failure is not an option and mistakes in school are bad because they cost you points–that failure and mistakes can actually be positive way stations towards improving our understanding of the world?

But in this book, suddenly there was answer in the form of nine dots and simple task. It read as follows:

“Please join all nine dots with four straight lines, without ever taking the pen off of the paper.”  img2

And the answer (sorry for the spoiler), which almost no one can get, is…


The secret here is that to get it right we need to “break out of the box” by having our lines extend past the box made by the dots. Once seen, it feels so simple, yet I struggled with this for five solid minutes before I turned the page in a fit of frustration to find the answer. Benjamin and Rosamund Stone Zander explain that what makes this so tough is that, “The frames our mind creates define–and confine–what we perceive to be possible.” In the case of the dots, the mind sees the square as a box that confines where the line can go.

The solution they offer for both the dots and other problems in our lives is that we need to “create another frame around the data,” which will help “the problems vanish, while new opportunities appear.”

This line was a revelation for me because up until that point I mainly tried to help students deal with mistakes and failure by building up their motivation, mindsets, and sense of belonging–all of which have been proven to make kids more likely to persevere through adversity. And while that was effective in many cases, I realized that if I reframe how students view mistakes and failure in my classes, I can likely help even more students, and especially the most vulnerable ones, to not be knocked off course when they hit problems along the way.

The way I plan to approach this is to take inspiration from a study done by Gregory Walton and Geoffrey Cohen where they studied African American students at colleges with alarming drop out rates. In the study they found that a one hour session at the start of the year where current and former students discussed how it is normal to feel a lack of belonging at the start of college (which appeared to be a major culprit for the dropout rate) halved the achievement gap, dramatically slowed the rate of dropping out, and led to them being measurably happier and healthier at the end of college and even when they were 25! The thought is that this one session was so effective because it offered a “new frame” for the students to view social problems in those first months. While the problems the students faced likely didn’t change, what did change was the way they viewed them. Feelings of unease and outsiderness were normalized, which gave students the opportunity to view the feelings as normal and temporary and something they could eventually most past.

This is exactly what I want to do with mistakes for my students. Instead of just hardening students against failure ahead of time or downplaying any negative feelings (which is the norm in the many rose-colored stories about the “positives of failure” that one finds from a litany of famous and wildly successful people), I want to reframe failure as the study did. I want to acknowledge that mistakes and failure can make us feel frustrated, embarrassed, or guilty while also explaining how mistakes and failure can be one of our most valuable teachers if we let them. The idea here is to normalize the negative feelings, making them less paralyzingly scary, while also reminding students of the potential positives that failure can bring to act as a motivator to help them push through the missteps they encounter along the way!

Thanks as always for reading!

Yours in Teaching,


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3 responses to “How I Teach My Students to Fail Forward”

  1. The Art of Possibility is a GREAT book! I’m so glad you are doing the work you are doing in regards to reframing mindset with your students. We really need more of that — especially in regards to writing. (I suspect many teachers could use this advice too as they work to examine and overcome their own writing history.)


  2. Isn’t it such a wonderful read! The timing with the beginning of the year was perfect too! And I completely agree with you about the idea of needing more reframing for both students and adults. We instinctively swerve around obstacles, mistakes, and failure, so it is important to regularly check our mainframes concerning them. Thanks for reading!


  3. […] to be something more positive–a necessary way station on the path to learning. I wrote a whole post on that, but it is nicely summed up by this quote from Neil Gaiman that I start with on the first […]


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