How I Got Started Tutoring

Professional tutor and guest blogger Josh Sohn's story about why and how he found success in the tutoring industry.

It was July 2001 and I needed a job. A real job. I’d graduated from Wesleyan University a year earlier and, somewhat incredibly, managed to land an apartment on St. Marks Place a few doors down from Grassroots Tavern. That was before Chipotle. And Bubble Tea. And Vapes. (Even cell phones were something of an oddity then.) It wasn’t as though I’d spent a whole year doing nothing. I had a job working in the Writing Workshop at Cooper Union where I tried to coach uninterested engineers through James Joyce and Amy Tan. I’d even taught ESL at CUNY, though strictly part-time. But it wasn’t enough. I needed a real job that paid real money so I could do real things. Like pay for the trip to Europe I’d just taken.

Twenty-three is a particularly evolved age for whining and I was brimming with recent postgrad entitlement. I’d written my thesis on the Gothic Novel — I was certain I knew everything. My sister, five years older and immeasurably more practical, suggested I try tutoring. I was skeptical. The idea that parents would pay me to tutor their sons and daughters (over whom I held a perilously small age advantage) struck me as both incredible and unlikely. But, when your older sister tells you to do something in the name of landing a real job which, if a) real and b) attainable, would allow you to live on your own in NY, you do it.

A few weeks later, the same friend I’d gone to Europe with, Reggie, and I were stapling flyers to telephone poles in and around New York City. Our big innovation? Pull most of the phone number tags from the flyers to suggest existing interest in the product. We reasoned it’d be easier for parents to give us a try if they felt other people already had.

Reggie was considering medical school at the time (he’s now a neurosurgeon) and we mused about being a two-headed monster: he’d handle the science and math tutoring and I’d cover the humanities. But the phone would need to ring before either of us could handle anything. That was early August. A week passed. Nothing. Another week: a wrong number. Finally, we got something. A woman was looking for a tutor for her son, a rising 9th grader at a school on the Upper East Side. She was just starting her search and had seen our flyer near a ferry in Long Island. She’d noticed most of the phone tags were gone, so she figured we must’ve already attracted some interest. (!) Would we be willing to come to her office in midtown for an interview? Yes. We would be willing to do that.

A few days later we were sitting before her, explaining ourselves. What sort of tutoring experience did we have? None really. How about existing clients she could speak to? Working on it. Curriculum? Sorry. Pedagogical principles? That one we could answer. We both loved learning and always had. Especially interdisciplinary learning. And we would bring that enthusiasm to our students, starting with her son. If she’d let us. All we really had to offer was enthusiasm — there was no way she’d hire us.

But she did hire us.

And then someone else hired us. And then someone else after that. And sixteen years and thousands of students later, I’m still tutoring. Because I genuinely love it. Because it’s challenging and new with each student. Because I get to connect ideas across disciplines. Because who doesn’t love to learn.

Recently, I reconnected with that original student. He’s 30 now. He couldn’t believe I was still tutoring all these years later. Then his eyes lit up. There was an opening at his design firm that he could recommend me for. What would I say to finally having a real job?! I told him I’d think about it.

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