From Entrepreneur to Educator: A Conversation with Second-Career Teacher Ben Coleman

Ben Coleman dropped out of college to start a computer business.

“I was making so much money in computers that I didn’t see the point in college,” says Coleman, who abandoned his engineering studies to operate a series of computer stores.  His decision seemed to be a sound one — until the Internet transformed the industry.

“In 1999, I was offered $2.4 million for my computer business,” Coleman says. “I sold it in 2001 for $30,000.”

Coleman headed back to school. Instead of completing his engineering program, he decided to pursue a career in math education. “One of the reasons I dropped out of engineering in the first place was because my math was so weak,” Coleman explains. “I realized that the math I’d learned in school wasn’t enough to support that trajectory and felt cheated.” Today, Coleman is an eighth-grade math teacher at Talbott Innovation Middle School in Fall River, Massachusetts.

We recently asked Coleman to reflect on his experiences as a second-career teacher.

What’s the connection between business and education?

One of the things that’s great about teaching is that your job tends to be very secure. There’s a huge shortage of math and science teachers right now, so my job is very secure.

The other thing that’s cool — and almost entrepreneurial — is applying for grants. I teach in a struggling, urban inner-city district, so we’re a prime candidate for grants. This year, I wrote a grant proposal, and we received a grant to send an experiment to the International Space Station. I’ve also worked on grants that helped us secure funding for our after-school program.

This entrepreneurial aspect of teaching is widely misunderstood.

Tell us a little bit about the first time you were in a classroom as a teacher. What was that like?

Terrifying. To be honest, the first three months were terrifying.

I’ve learned that new teachers go through a predictable cycle. There’s this initial enthusiasm, and then about a month into teaching, depression sets in as you realize that you’re not going to be able to do all of the things you thought you could. You confront all of the fantasies you had about the job. But if you keep going, you eventually start reflecting on everything the kids have learned in the course of your time together. That’s something that is very powerful, and if you can cling to that, you will stay in teaching forever.

What advice would you give to someone who is considering transitioning to a career in education?

Be careful what state you locate yourself in. Some states are liberal about granting initial licensure, and other states have really rigorous requirements.

Also, the first year is really tough. The key to a healthy relationship with your class is to admit mistakes; kids can tell if you’re being truthful.

One of the worst things you can do is to get all excited about a lesson you’re going to teach, thinking it will be the greatest lesson in the world. Then if some kids start misbehaving during your lesson and your lesson bombs, you’ll start blaming those kids for the lesson bombing. Before you know it, you’ve got a resentment against those kids, and they build a resentment against you, and it all gets messy. So the key is not to over-plan things. Admit mistakes, don’t over-plan and concentrate on positives.

For you, what was the most difficult part of transitioning to a career in education?

Not being in charge of everything. In my former career, I was the boss, and I was in charge of everybody and everything. Today, I’m only in charge of what happens behind my door. As soon as I get in the hallway, somebody else is boss.

Do you think your previous career experience has been an asset?

What I see in a lot of people who come into teaching as a second career is a refreshing approach. You’ll see teachers who haven’t come through traditional licensing programs doing all sorts of unconventional things with their classes — things like taking students outside, having them experience things firsthand rather than through books. We have a science teacher here who’s constantly taking his kids outside, to the consternation of our principal.

I’m teaching kids math, science and problem-solving through our International Space Station experiment. We’re going to send tadpoles to the International Space Station, so we have multiple experiments going on right now. We’re trying to figure out how long tadpoles can survive without food, because if we can send up an experiment where they don’t need to be fed much, it’ll be much, much easier than trying to rig up a feeding system. We have other students designing aquariums that are capable of handling 2.5 g-forces.

One of the really cool things is that I spent nearly three years studying engineering, and now all of that is suddenly relevant again.

Do you think enough support and resources are provided to those who come to teaching as a second career?

Districts have to have a mentoring program in place for new teachers. They need to allot extra time for teaching teachers. If the district doesn’t have a mentoring program (sometimes called an induction program), I’d avoid that district.

If you could change one thing about the current educational system, what would it be?

Every school in the United States is about 15 to 20 years behind every business in the United States in terms of computerization. We are wasting vast resources on old systems that don’t work and are totally capable of being computerized.

In my school, students need passes to be in the hallways during class time, so we have to write out all these passes for students. If a student wants to go to the bathroom, I have to stop my lesson and fill out a pass. That student already has an ID card with a barcode. There should be a scanner at my door, and if a student needs to use the bathroom, they could simply scan their card, press the bathroom button and go.

Jennifer L.W. Fink is a freelance writer who frequently writes about education, health and parenting. See her work at and