Pro Tips for Full-time Tutors and After-School Moonlighters

As a tutor, Josh Sohn doesn’t simply help students complete their homework or ace their SATs. He tries to make learning profound, “lift and support” the kids he works with, and demonstrate an engagement some parents just can’t provide; he even helped persuade one student not to drop out of school.

Passionate about education but unsure if a traditional teaching path was for him, the Brooklyn native was uncertain of his next step after graduating with an English degree from Wesleyan University in 2001. At his sister’s urging, he launched a tutoring business as a way of testing the education waters. Before long, he was a full-fledged—and busy—entrepreneur.

Since taking that leap 17 years ago, Sohn has come to learn that a tutor can have immense significance in a student’s life. He talks to EdSurge about the joys and challenges of creating a full-time tutoring career and shares advice for other tutors as well as educators considering the profession.

EdSurge: When did you first start thinking of yourself as an entrepreneur?

Josh Sohn: Honestly, I didn't really think it was going to work. I was pessimistic. But I got supremely lucky. I put up thousands of flyers all over New York City, and a couple people responded. But one of the people who responded needed a lot of support for her son. That was game changing for me because for most tutors, you build your business one student at a time. And the first student I got needed 10, 15 hours of support each week.

All of a sudden, it became a viable career, and I thought, ‘Oh, this is totally easy.’ Of course, it was a long time before I was able to tack on other meaningful clients. So, it was a great lesson in being neither vain nor overly humble.

How does tutoring mesh with your creative life?

Tutoring gives me room for both. I have creative pursuits, most notably playwriting, but even continuing to write fiction.

I’m also trying to build a successful business, and be a full-time tutor. It's always been fulfilling and satisfying.

What are the most common headaches in tutoring?

Honestly, parental engagement can lift or completely sink work that's being done. I've walked into households where I'm working at a kitchen table with a student, and family members and parents are watching television at high volume right next to us. That's a difficult spot to be in as an educator, feeling like you have to convince both the kid and the parent that the work you're doing is important.

The more mundane challenge is certainly just getting kids to do the homework, particularly when it comes to test prep.

How have you overcome these challenges? Does technology help?

There are occasions when I've suggested a venue change. Usually meeting in a student's home is preferable for clients, but in some cases, I haven’t presented that as an option. When a student to comes to me, I have a much greater degree of control over what the learning environment looks like.

I also see about a quarter to a third of my students via Skype or FaceTime—that way what's happening in my home over my shoulder is quiet and rigorous.

We have the tools at our disposal now where kids should not need to wait days, weeks, months to find out how they did on something or whether they're on the right track. Not only is that inefficient, but it's not necessary. I’m a big fan of using Quizlet and IXL in my test prep to encourage students and get them feedback right away. They are available to kids 24/7 and allow students to get instant feedback—and feedback is how people learn.

I think that's why Clark—the software I use to manage my business—is so exciting. They're trying to bring some systems to a really disorganized and pretty high-risk and high-stakes community, and succeeding at it. They're becoming not just tutor-facing, but more parent-facing as well. I'm hopeful that my relationship with them and my presence online with them will help generate future work.

Can you share a success story?

I try to make learning as profound for as many of my kids as I can, and I think there's an opportunity to really, really lift and support kids who aren't getting that support elsewhere.

I had a college student I was working with who was going through some profound stuff with his parents and was very much thinking about leaving school. He ended up staying in school. And while I won't pretend that it was solely because of me, I do think it's undeniable that a tutor has an ability to talk to a student in a way that a parent doesn't. It's just a different relationship. Of course, some of that depends on the age of the tutor and the age of the kid, and the type of work you're doing.

How has technology changed the business side of tutoring?

Right now, I'm seeing 30 or so students. I used to deal with a lot of accounting, invoicing, PDFs, and just keeping track of who's paid me. So every time someone was delayed in payment, every time someone wanted to change something last minute, that really took a toll. But Clark, which is basically a virtual assistant for tutors, has been an amazing help to me.

We live in an age of data. Do parents have expectations from you around data tracking and analysis?

Absolutely, it’s not exactly new information that data makes the world move. In the 15 years I’ve been tutoring I’ve seen a shift in my clients’ expectations about what I can bring them as a specialist—they expect a data-driven approach. And if I don’t tell parents and prospective clients what they want to hear, it’s easier now than it’s ever been for them to go find someone else.

When it comes to testing, it really is about the numbers. We hate to say it that way. But if you’re really helping someone prepare for a test, yes there’s value in the process and yes there’s growth that happens that’s independent of the final score, but the top objective is to deliver. I wholeheartedly believe data is the key to that.

Clark helps me communicate that data efficiently and clearly to parents. The feature that I use more than anything else is the session report functionality. It’s something that I have often thought I should be doing, but until this tool arrived in my life I was only doing it very informally and infrequently. The ability to capture what happened in the session—and have it packaged and delivered to clients—has absolutely been a boom to efficacy. Parents feeling looped in isn’t just good for generating business, it’s crucially important for delivering good outcomes.

What do you say to teacher friends who are considering moonlighting as tutors?

It's a great source of pride to me that this is my full-time occupation. But I think there are a lot of tutors who just don't think of tutoring as a real craft. That makes me sad.

This is serious business. You're talking about test prep and college applications and grades, to say nothing of kids who are contemplating leaving school or dropping out. These are real people with major challenges—in many cases with really tumultuous relationships with the adults in their lives.

I feel like even if you're just doing it part-time, it's important to understand the gravity. Of course, it can be fun and revelatory, but it's also serious work.

What’s the most rewarding part of tutoring?

The most rewarding moment I experience as a tutor is often the most wrenching. It's when students and I close our work together, and I do my best to take stock of the changes we've both undergone. Sometimes that's connected to a specific exam or application, but more frequently, my work with students concludes when they're accepted to college.

I've worked with about 1500 students over my career, so I've said goodbye to quite a few young adults. Come to think of it, many of those individuals are full-fledged grown-ups by now.