With AI, are we losing the courage to fail?
In a world of AI, human imagination still matters
Come to Dance My Joy by Moe Brooker. Photo by Libby Rosof.
Before studying psychology, I had studied fine arts—specializing in painting and drawing. I had the great privilege to be advised by the brilliant painter Moe Brooker, who sadly passed away in 2022. His work was extraordinary, like nothing I had ever seen: large life-size drawings made with pastels and acrylics that brought to mind jazz-- improvisational, rhythmic, colorful, and utterly original. Oh, we students all wanted to be as innovative as he was.
As an African American artist, Moe faced many obstacles. As a teacher, he taught us to explore, to experiment, and to push conventional boundaries. Looking back, he taught me far more than art technique—he taught me a way of thinking.
One day in a drawing class, we did an exercise making abstract drawings, to experiment with principles of harmony, rhythm and color in design. Then, we hung our pieces on the wall for a critique--there were maybe 25 drawings. Moe carefully examined all of them walking down the line. He had a commanding presence. He stopped at one, hung at the very bottom.
He then turned to face the class and asked loudly: “Who did this?”
The picture was frankly terrible. It violated every principle we were taught. But no one spoke up. It wasn’t my picture, but like everyone else, I was terrified for the person who would be outed. We stood frozen. Moe repeated, even louder: “Who did this?” Still, no one said a word. No one wanted to get shamed in front of the whole class. Moe stared us down, and finally we heard a timid voice: “I did.”
To our complete surprise, Moe then beamed and said “Congratulations, you had the courage to fail.” Then he gestured to the whole lot of drawings and said: “These others are too safe. They’re not taking any chances. This drawing is the best because this person took a risk. And risks lead to discovery.”
That moment stayed with me. Moe had named something essential—not just to art, but to thinking, and to life: the necessity of failure, and more precisely, the value of daring to fail. History is full of wild ideas that seemed destined to fail. A heavier-than-air flying machine? That was the Wright brothers. Having strangers sleep in your home? That became Airbnb. Creating radio dramas to sell soap? Those became soap operas. Audio shows made by amateurs? Who would listen? Those became podcasts. A reusable adhesive? What would you do with that? It was used to create post-it notes. Most crazy ideas don’t work. But some do.
Learning to have the courage to take risks and fail is about developing a mindset: a willingness to take bold conceptual leaps and to let oneself plummet. As a student, and later an educator myself, Moe Brooker’s teaching made me see how schools typically don’t teach this kind of thinking. Students are rather taught to not make mistakes, to not stumble. In a competitive climate, where college slots and jobs are at stake, there is no room for risky thinking that can lead to failure.
Children are punished for mistakes in school with lower grades. So they play it safe. But what if we flipped that around? What if children were taught how to think boldly, and even encouraged to fail? What if we rewarded unconventional ideas because they reflect daring, creative thinking?
There are schools that do this. High Tech High in San Diego and NuVu Studios in Cambridge, MA are nontraditional learning environments where students are encouraged to take risks and experiment with ideas. Graduates have gone on to top colleges like Brown. Montessori and International Baccalaureate programs also emphasize risk-taking as part of learning. But these schools are exceptions.
In traditional learning environments, failure is still seen as a setback. But failure is information, it’s feedback, it’s data that one can utilize. Rather than traumatizing a student for failing, schools should help students see failing as a necessary step in the path toward learning.
As AI use becomes more commonplace by students and workers, the willingness to take risks and fail may fade entirely. Yes, AI hallucinates still, but these errors will decrease as the technology improves. AI saves effort, and produces flawless, polished outputs.
Students now use it widely. A study last year by the Digital Education Council reported that 86% of students use AI in their studies. Many schools are working hard to formulate policy for use of AI but restricting its use outside of the classroom is nearly impossible. Educational institutions are grappling with how regulation can keep pace with AI development and use but it’s like trying to write the rules for a game that keeps reinventing itself.
With AI, students won’t have to put in the work to think hard and ideate. Rather, they just need to learn how to refine prompts. The result is low effort and safe thinking on the part of the user. Even in a subject like history, innovative thinking deepens understanding and retention of the information.
So then why should we care about teaching students to have the courage to fail?
The reason is that failure is what sparks learning. We can fail and feel defeated and miserable. Or we can fail, and view it as an opportunity, a freeing experience, to explore and do something greater than imagined.
My dream of education is that young people would be rewarded for failure and for failing boldly. Failure would be recognized as the evidence of thinking big. My hope is that students’ fulfillment in thinking creatively would overshadow their desire to use AI to think for them.
What if schools awarded prizes for the craziest ideas that shouldn’t work? I’d call it the Moe Brooker Prize. What if students worked in teams not to come up with successful solutions, but to generate the most outrageous, imaginative ideas that couldn’t possibly work? Not only would it be fun, but it would teach teamwork, cultivate divergent thinking skills, develop resilience, and would also reduce the stigma of failure.
Failure is human, and it leads to growth. It’s the opposite of perfectionism. Striving for perfectionism masks a fear of failure. Young people are still developing their minds, and when young it’s a chance for them to stretch their imagination and to have the freedom to think in ways without experiencing repercussion for failure. Relying on AI will only lead them to circumvent the chance to think big.
In our conversations about AI, we’re generally focused on the efficiency and the conservation of our human energy. But we rarely ask what users lose by not engaging deeply or daring to think big. Relying too heavily on AI can short-circuit the creative process and rob young minds of the opportunity to dream wildly. Thinking safe stifles discovery.
After all, it’s often the bold, uncertain leaps that lead to truly transformative ideas.
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You can learn more about how technology is affecting our minds and behavior in my book Attention Span, now in paperback with new exercises.