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In 2016, I was running six schools I had founded in six years. And I was completely spent. I started getting alarming signals from the people in my life. Friends would pull me aside and ask if I was ok. My clothes weren’t fitting quite like they used to. I was irritable with the people around me. I gave my board notice that February, and after a nearly yearlong search and selection process, I left the network and moved back to New York City. 

The cliché to describe my condition was burnout, and I had all the textbook physical signs. But something else had happened too: I’d lost my curiosity. 

Like many educators, I got into the work of schools because I loved learning. Somewhere along the way, though, I became so consumed with everyone else’s learning — students, teachers, principals — that I stopped paying attention to my own. The best educators somehow manage to remain students themselves. I hadn’t. I was increasingly skilled at organizing other people’s intellectual growth while neglecting my own. I was at risk of becoming one of life’s most depressing archetypes: a competent bureaucrat. 

I thought leaving schools meant I was taking a break from education. Instead, the next several years taught me more about learning than almost anything I had done as a superintendent. 

My turning point came about a year after leaving school work. I was at a wedding watching the DJ spin salsa music as a few intrepid guests hit the dance floor. It reminded me of all the times I’d started to learn salsa dancing and quit. 

Then came the flood of memories of other abandoned ambitions: the novel I had started and stopped many times, never getting much beyond a few pages; my repeated attempts to become fluent in Italian; the many sports I’d wanted to learn. When I got home, I took out a notebook and wrote them all down. The list included some relatively simple items, like playing guitar, and some much more ambitious ones, like flying airplanes. 

I decided I would tackle one item each year. Without realizing it, I had recreated school for myself. Every year would be devoted to a single subject, with a curriculum, benchmarks and a final exam. This time, the only student was me. That experiment became the basis of my new book, . The book is geared toward people from all walks of life, but it’s particularly salient to educators. 

During my first year, I took on powerlifting because I wanted to reclaim my strength and overall physical health. I wound up entering a powerlifting competition and taking home the top deadlift in my weight class. During the next year, I learned screenwriting and signed with CAA, Hollywood’s most powerful agency. Then, during the height of the pandemic, I learned to surf. After that came tennis, novel writing, biochemistry, and Italian cooking. 

I’d be lying if I said external validation and achievement didn’t matter. But the most lasting benefits were what those experiences taught me about learning. I couldn’t help approaching each pursuit like a school leader. 

At the beginning of every year, I built a scope and sequence. I identified the component knowledge and subskills, put them in a logical order and established benchmarks along the way. The same process we had once used to break a seventh-grade math standard into teachable steps now became a way to deconstruct a deadlift, a tennis stroke or the metabolism of glucose.

Every year also ended with a final exam, though not necessarily a written one. In powerlifting and tennis, I entered competitions. During my biochemistry year, I took the MCAT. During my Italian cooking year, I hosted a pop-up restaurant for friends and invited a food critic from New York magazine.

I now believe every educator should deliberately become a beginner at something on a regular basis. You can fool yourself into thinking the books you read or the pedagogy workshops are enough to make you an expert. Those can add value. But they cannot reproduce the cognitive and emotional experiences our students face every day. The fear, embarrassment, bewilderment, failure, and, of course the joy of finally getting it right. 

To put it somewhat harshly, if you haven’t been truly bad at something lately and climbed your way to proficiency or mastery, then you are out of touch. I certainly was. I thought I was an expert on learning when I was a superintendent. Yet every step of my personal learning journey deepened or expanded my practice. Sometimes, it even exploded my orthodoxy.

For example, I’ve long been a skeptic of group work. Too often in classrooms, “collaboration” means one student doing the assignment while everyone else free rides. Then I spent two months in a Tuscan kitchen and watched how tacit knowledge got transmitted sideways  from watching, imitating and being corrected by my teammates. 

I was also a bit of a personalized-learning skeptic because I’d witnessed countless schools oversell their technology in service of getting funding and attention. But during my biochemistry year, I was blown away by the quality of online content. 

This was worlds away from when I was in college. Back then, we got exactly one explanation of the citric acid cycle from our professor and maybe another from the one textbook we were assigned (which often was written by the exact same professor). Now with the push of a button I could access thousands of high quality videos from experts competing against each other to offer the best explanation. 

This challenged my view of the role of teacher. Explanation of content is simply less important now than it was when I ran schools. And with the advent of AI tutoring, we also have new and powerful avenues for differentiation. 

Other lessons were less about changing my mind than about turning theory into practice. I’d long had a superficial understanding of educational concepts like cognitive load theory, the Feynman technique and spaced repetition. But preparing to take the MCAT forced me to use those practices every day, sometimes under extreme pressure. 

And sometimes, being a student gave me a newfound appreciation for methods I already believed in. When I ran schools, we were fanatics about videos. We filmed teachers constantly and broke down classroom instructional tape like NFL coaches. We’d tag and save examples of excellent teaching (inspired by the work of Doug Lemov) and we’d watch our mistakes on repeat until we could decode what went wrong. 

I was almost always the one behind the lens, but years later, learning to surf, I was on the other side of the camera. My coach would film me taking all kinds of undignified falls. We’d watch the tape together, drill on land, then try again the next morning. For the first time, I understood how vulnerable it feels to watch yourself screw up. And I also gained a deeper understanding of how to pair the video with immediate practice. 

It’s easy, after years of evaluating others, to become an expert observer of learning. The harder — and more important — task is to remain a learner yourself. Which is why, after all of these years, my one-room school is still open. And my list keeps growing. I haven’t yet crossed off flying airplanes or salsa dancing, but I know I’ll get there someday. 

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