Educator Argues Hobbies Are Essential for School Leaders
A former school superintendent writes that educators must regularly become beginners at new skills to stay connected to the student experience.

A former school network leader says educators risk becoming out-of-touch bureaucrats if they do not regularly experience being a beginner. Ankur Gupta, who founded and ran six schools, writes that reclaiming his own curiosity through serious hobbies taught him more about learning than his time as a superintendent.
Gupta left his school network in 2017 after experiencing burnout and a loss of personal curiosity. He realized he had become skilled at organizing learning for others while neglecting his own. About a year after leaving, he decided to tackle a list of abandoned personal ambitions, devoting one year to each. He called this experiment his 'one-student school,' which became the basis for his new book, The Invisible List.
The Personal Curriculum
Gupta approached each annual hobby with the methodology of a school leader. He built a scope and sequence, breaking each skill into component knowledge and subskills. He established benchmarks and ended each year with a 'final exam.' This often took the form of a public test of his new ability.
| Year | Pursuit | Final Exam |
|---|---|---|
| 1 | Powerlifting | Entered a competition, won top deadlift in his weight class |
| 2 | Screenwriting | Signed with Hollywood agency CAA |
| 3 | Surfing | Learned during the height of the pandemic |
| 4 | Tennis | Entered competitions |
| 5 | Novel Writing | Worked on a manuscript |
| 6 | Biochemistry | Took the MCAT exam |
| 7 | Italian Cooking | Hosted a pop-up restaurant for friends, invited a food critic |
Transforming Educational Practice
Gupta states that the cognitive and emotional experiences of being a beginner deepened his educational practice. He says, 'if you haven’t been truly bad at something lately and climbed your way to proficiency or mastery, then you are out of touch.' His hobbies challenged long-held beliefs about teaching methods.
For instance, he was a skeptic of group work, often seeing it as one student working while others free-ride. However, spending two months in a Tuscan kitchen showed him how tacit knowledge is transmitted through watching and imitating teammates. He also gained a new appreciation for online personalized learning while studying biochemistry, finding thousands of high-quality videos from competing experts.
This changed his view of a teacher's role. 'Explanation of content is simply less important now than it was when I ran schools,' he writes. He also notes the potential of AI tutoring for differentiation.
Turning Theory into Vulnerability
Other lessons involved applying educational theory under pressure. Preparing for the MCAT forced him to use practices like cognitive load theory and spaced repetition daily. He also gained a new perspective on a method he already believed in: instructional video.
While leading schools, Gupta's team filmed teachers constantly to analyze instruction. Learning to surf, he was filmed by his coach taking repeated falls. Watching those tapes gave him a firsthand understanding of the vulnerability students feel. He learned how to better pair video feedback with immediate practice.
Gupta argues that the harder task for experienced educators is to remain a learner, not just an observer of learning. His personal one-room school remains open, with flying airplanes and salsa dancing still on his list to master.





