Failing Forward

How to Prepare Schools for the Future One Mistake at a Time

“Failure is a gift. Successful risk-takers are often motivated by failure—it’s what tells them that they aren’t done preparing yet. It’s inspiration to work harder, to train better, and to learn more. They understand that mistakes have the potential to offer them as much, if not more, than success in the way of both data and experience. They don’t take failure as a sign to stop.” – Kayt Sukel, The Art of Risk  

Projections around life expectancy tell us that sooner rather than later, humans will regularly live to 115 years old . This rise in life expectancy will add an additional 35 years to the average American life. In many respects, an increase in life expectancy feels like progress; however, saving for what could be 35 additional years of retirement is not an option for many. In all likelihood, a majority of these additional 35 years will be spent working. By adding decades to one’s work life, it is perfectly plausible, even likely, that students who are in the 5th grade in 2022 will still be part of the workforce come the 22nd Century. 

In the midst of the Fourth Industrial Revolution, we are stuck in patterns and habits from the Second Industrial Revolution. We are seeking to prepare students for the 22nd century using systems that are still largely indistinguishable from the early 20th century. If schools do not change, we only continue to stifle our capacity to truly help students prepare to navigate complexity, adapt to uncertainty, and thrive in a future of their own design. Schools must be in a constant quest to identify and equip students with the skills they need to successfully navigate the unknowns of the emerging future. Of course, it’s daunting to decide on the directional vectors that are going to spur the sort of change that actually prepares 5th graders to live on the moon. 

Fortunately, success isn’t predicated on big, fundamental changes. As Robert Slavin wrote, “No one ever built a cathedral by waving a wand. Instead, magnificent cathedrals are built one stone at a time.” Change is accomplished through an accumulation of small, iterative shifts – shifts that are the byproduct of expertise and dedication, of course. But also the result of purposeful risk-taking and measured experimentation. 

We must admit, however, that risk-taking and experimentation can be in short supply in our classrooms. Even teachers cognizant of the dreaded acronym TTWWADI can sometimes find themselves in a rut, subconsciously avoiding change. This is no surprise as risk-taking and experimentation require us to do something incredibly difficult – to accept failure. It’s one thing to intellectually understand that not every risk will bring reward. But it’s another to actually take that risk and then fail. No teacher wants to feel they are “failing” their students. 

And so, as school leaders, it is incumbent upon us to help our teachers to become confident risk-takers by fostering a culture that embraces, even celebrates, the most atomic building block of innovation – failure! 


Here are a few talking points you can use to help compel them to be the sort of confident mistake-makers that will drive your school forward:

You Set the Tone

At some point during Thomas Watson’s tenure at IBM, a promising junior executive was involved in a risky venture for the company and managed to lose over $10 million in the gamble. It was a disaster. When Watson called the nervous executive into his office, the young man blurted out, “I guess you want my resignation,” to which Watson replied, “You can’t be serious. We’ve just spent $10 million educating you.” Most people have been socialized to avoid failure. We also know that this response is exacerbated in the workplace when we, as school leaders, display aggravation, annoyance, or antipathy in the face of it. As school leaders, we can change the way our faculty perceive failure by taking a page out of Thomas Watson’s leadership playbook. By responding to failure with a future-facing orientation, we incentivize the pursuit of future learning. 

Don’t Forget to Laugh

Research has found that humor can positively influence learning after a mistake. Humor, it turns out, is a dispositional hinge point that can defuse the self-admonishment that may naturally arise following failure. When you respond to failure with a magnanimous chuckle or genial grin, it can translate into your faculty doing the same. Humor has a much more leveling and comforting effect than many might admit, so when we approach failure with a sense of humor, it can translate into those around us doing the same -- chuckling at their own absent-mindedness before embarking on the serious work of learning from the mistake. 

To Err is Human (but don’t take it personally)

In 1985, President Ronald Reagan visited a German military cemetery in Bitburg, Germany to commemorate the 40th anniversary of the end of World War II. This visit, soon became a lightining rod of controversy as it was revealed that some of those buried in this cemetery were Nazi SS officers. Shimon Peres, the Israeli prime minister at the time, responded to a reporter's question about the brewing controversy by saying, “When a friend makes a mistake, the friend remains a friend and the mistake remains a mistake.” If we are to remain open to learning from our mistakes, Peres provides our roadmap. ‘When I, a decent, well meaning person make a mistake, I remain a decent, well meaning person and the mistake remains a mistake.” When a decent, well meaning teacher makes a mistake, they remain a decent, well meaning teacher – no mistake can change that. If we want teachers to be confident risk-takers, we need to remind them that their failures do not define them. By helping our teachers to disentangle themselves from their failures, our teachers are more likely to focus on remembering what went wrong and learn from it, as opposed to harping on it.