Why Teachers Make Great Entrepreneurs

Teaching How to Catch a Crab. Photo by Mason New

The best teachers I knew were entrepreneurs. No, not in the sense of leaving the classroom to start a business and somehow becoming wildly financially successful. Sure, you can find those examples published in all sorts of media. Rather, I mean entrepreneurs in the sense of people obsessed with solving problems, delivering clear and effective communication, and understanding the basis of our entire society: human relationships.

Teaching is damn hard work. It requires long hours, low salaries, constant conflict of one sort or another with all kinds of stakeholders, and dealing with younger people. At the same time, it provides “psychic income” in excess of almost all other professions. The teachers who care most about their students get paid in treasure everyday.

So, who are those who care so much? The ones I knew organized every moment in order to achieve the maximum amount of learning for the maximum number of students. They held themselves to the same rigorous standards they asked of their students. They executed on their personal mission: learning first, content second, conveyed in multiple ways and diverse formats. Not an easy task because human beings, in case you didn’t know, don’t absorb information just because they hear it. As one of my wise colleagues advised me early in my career, “Just because you say it doesn’t mean they learn it.”


Entrepreneur: a word today batted around like a July 4th shuttlecock. Until recently, however, I didn’t know its origins.

The word comes from the French “entre,” which means “between” or “up,” and “prendre”, which means “to take.” So, one might literally say, the word means “to take up” or “to undertake.” Seems simple. An entrepreneur is someone who takes up something.

A few weeks ago the Wall Street Journal published an article citing that during COVID19 shutdowns, people in the United States are launching businesses at a rate never before seen and for myriad reasons: losing a job, focusing at home on problems to solve, scratching the entrepreneurial itch, searching for additional income, and so on. I believe people are gaining new perspectives, no longer saddled with inefficiencies — commutes, purposeless meetings, people in the office stopping by to “chat” about random topics. A shutdown has taught many people to take charge of their destiny and lend their time and talents in meaningful ways. I know many people who want to “take up” the endeavor and contribute.

For these reasons, great teachers can make excellent entrepreneurs. Of course, academic skills and business skills differ entirely, and creating a business enterprise and securing customers in a competitive market have zero similarities to teaching a class to a captive audience. The market demands financial risk and uncertainty, profit/ loss statements, and revenue projections, not words commonly associated with teaching. However, like the entrepreneurs so often lionized in the media, great teachers are great problem solvers, committed at their core to delivering what is useful and valuable to their customers, the students.


In my work, I have had the great fortune to speak with numerous entrepreneurs who started their careers in teaching. Many of them launched tutoring businesses. In fact, I interviewed several and wrote these success stories for my client, Trilogy Mentors. In every single case, the entrepreneur at the heart of the business unequivocally stated she or he wanted most to help students. Yes, they operated a commercial enterprise, but at its core, each business served first the mission to help solve learning problems for kids.

COVID19 has exposed many of our most pressing problems in education. Right now, millions of children attend school in dozens of different formats: online, hybrid, in person, or most problematically, not at all. Pods. Homeschool. Different regions with different instructional delivery. However, as with most powerful forces, the destruction of old ways creates new opportunities and new methods. For the teacher/ entrepreneur, conditions are perfect to effect meaningful and lasting change.

So, amidst this pandemic, if you feel the need to help kids, earn some income, and share your knowledge and expertise, launch your tutoring business now. Millions of students await you.

Thank you for reading.

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