This as-told-to essay is based on a conversation with Carter Osborne, founder of Carter Osborne Tutoring. It has been edited for length and clarity.
My business started for very pragmatic reasons: I needed to pay for graduate school. I went to Stanford for undergrad, and then enrolled at the University of Washington for my master’s degree. I was funding grad school almost entirely with student loans, and I thought tutoring could help me pay them off quickly.
I started by tutoring high schoolers in general academics, standardized test-prep (including for the SAT), and college essays. I quickly realized I didn’t enjoy the academics or test prep, but I loved working on college essays. I’ve always been interested in creative writing, and helping high schoolers tell personal, authentic, profound stories about their lives was so fulfilling.
I decided to become an essay specialist. That cut down my potential market, but also helped me establish myself as an expert. The business grew: in the first two years I generated a total of about $30,000 — almost what I needed to pay off my student loans.
I intended to quit tutoring, but the pandemic created opportunity
I graduated and got a job in public relations at a global firm. I had always been interested in government, and my job involved working on policy campaigns, so I really enjoyed it.
I always assumed I’d stop tutoring after grad school. After all, driving through Seattle traffic to meet each student in person as I had been doing would be nearly impossible with a full-time job. Then, the pandemic happened and everything pivoted to Zoom and video meetings. I hate to say it, but COVID was a lucky break for my business, because it meant I could layer tutoring on top of my full-time job.
I was working PR in the mornings, and tutoring teens working on their college essays on nights and weekends. I thought 2020 would be my last year of tutoring, but in 2021 new families who were referred by previous clients reached out. I thought I would be crazy to tell them no. Plus, I wanted to help.
Working both jobs became unsustainable
Every year I would say it was my last year of tutoring, but the business continued to grow through referrals. By 2022, I earned more tutoring than I did working in PR. By 2023, I was working with about 50 clients for 6 to 8 weeks at a time, usually for an hour each week.
All in all, I was sometimes working more than 80 hours a week. I would often start PR work at 6:30 a.m.; when that work day ended, I transitioned to tutoring until about 9:30 p.m. It was totally unsustainable. I barely saw my now-fiancee, my family, or my friends.
I wanted to copy myself, but since that’s impossible I knew I would need to choose between the jobs. I enjoyed them both, but ultimately tutoring was more fulfilling and more lucrative. I quit my PR job and started tutoring full-time in 2024.
I have three months off every year
Last year— my first full year of just tutoring — I made about $220,000. That’s a little more than double what I was making at my PR job. I’m currently charging $250 an hour for my services.
My busy season begins in May and peaks in November with early-decision deadlines. Those months, I can work up to 50 hours some weeks. I meet with students online, and my clients are now located all over the country, and I even have a few abroad.
The busy season ends in January, when most admission deadlines pass. After that, I have about three months completely off. The first month is spent hibernating and recovering — I’m exhausted by that point.
Then, I spend two months doing everything I can’t do during the busy season, like traveling with my fiancé and hosting friends. People keep asking what I do during the slow season, as if I should take on more work. For now, I’m very happy having that time off.
I feel incredibly lucky to have stumbled upon a way to turn my creative passion for writing into a lucrative career. Very few people get that opportunity, and I’m able to do it while also helping high school students learn more about themselves and their stories.
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