This as-told-to story is based on an interview with Seattle, Washington-based tutor Carter Osborne, who owns college essay consulting business Carter Osborne Tutoring. Osborne started tutoring as a side hustle in 2017 to help with tuition payments while in graduate school. In 2024, Osborne quit his job as a PR director to take the business full-time. The conversation has been edited for length and clarity.
Image Credit: Courtesy of Carter Osborne
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I turned my tutoring side hustle into a full-time business in January 2024.
There was a push and pull for me in this direction: The push was that it became challenging to balance both my full-time PR job and my college essays, which I considered a side hustle at the time, although it had grown to the point that it took up as much time as my PR job. During the busy college application season, I was essentially working two full-time jobs, and it just didn’t work anymore.
Then the pull was that I love the artistic and creative aspect of working on college application essays. I find it so personal and enriching in a way that PR just didn’t quite match. So I was like, Okay, I have a connection to something here that is generating a lot of revenue, as much revenue as my PR job, but it’s more enjoyable day-to-day. I like working with the kids. I like working on storytelling. By the time I made the choice, it had become fairly obvious which one was right.
Related: This Graduate Student Started a Side Hustle to Help Pay Tuition. It Earned Over $115,000 Last Year — More Than His Full-Time Job.
I had a vague idea that I wanted to increase my revenue by about double, thinking, Okay, I’ll have twice as much time and should be able to dedicate that to my business. I’d love to double my revenue. So I raised my rates, knowing that that was a stretch goal going in. Just because I’d freed up an hour didn’t mean I’d have that much more business. I had to go out and earn more clients and spend more time with them.
Between 2020, a few years into the side hustle, and 2023, I grew revenue from $58,000 a year to $114,250 a year. I had 37 clients in 2020 and 54 clients in 2023. When I took the side business full-time in 2024, I hit $222,000 in revenue with 66 clients. My business is highly seasonal. College application deadlines typically fall between November and January, so the second half of the year is the busiest. I made roughly 80% of my revenue last year between July and December.
During the busy season, I work 50 to 70 hours per week, depending on the month. October is typically the busiest as we approach the first major deadlines of the year, which fall on October 15 and November 1. During the off-season, I work roughly 10 to 15 hours per week, and I often step away entirely for vacations that aren’t possible during the busy season.
This industry runs on referrals; they’re the golden ticket. When parents want to hire someone to work with their kid on something as high-stakes as the college admissions process, frontline advertisements, social media marketing or other click-and-learn campaigns aren’t the way in for people because it feels a little too high-stakes and is often a multi-thousand-dollar commitment. Parents want to hear from their friend that they had a really good experience, and then rely on that barometer of trust to select a consultant.
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So, the more clients I work with, the more referrals I get for the following year. It’s an exponential increase, so often in this industry, starting out is quite slow, which is why I ran the business as a side hustle for a long time. As word got out, my name got around at different schools and communities, and because I went full-time last year, I had a lot more time to put into actively working my network to generate more referrals. And I generated enough referrals to meet my revenue goals. I was actually more excited about the number of clients I worked with than the revenue that I saw last year, because I knew it would set me up for even bigger years this year and then the following year.
Additionally, referrals from other consultants play an important role in the business’s growth. Currently, there is far more demand for services within the college admissions industry than there are professionals to provide them, so that means folks like me typically are fully booked every year. Nearly everyone in my network has filled up for this year; I’ve almost filled up. So that means we don’t have to be cutthroat and competitive with each other. I’ll receive referrals from other consultants whom I know and who trust me to do high-quality work.
I’ve also found that sharing my story with media outlets has helped my business get some attention, but interestingly, those pieces more often lead to messages from people who want to start a tutoring side hustle themselves, versus paying clients. I’ve been able to have a lot of great conversations with aspiring tutors.
Since I’ve taken the side hustle full-time, one of the biggest challenges has been staying on top of the administrative workflow. Now that I work with a lot more clients, I’m answering a lot more emails and addressing small questions that a student or a parent might have after our meeting is over. I do a lot more scheduling and onboarding calls with people. Even the time I spend billing and invoicing has gone up. So there’s a lot around the margins that I’m trying to make as efficient as possible.
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Down the line, I’d consider hiring someone to help with the administrative side, and by next year, I’d definitely like to hire tutors to work with me. I’d like to bring someone on to help with editing and a little bit of the at-home essay work that I spend a lot of my time doing. But I like to be hands-on with that and am hesitant to hand that off to anybody else whom I haven’t thoroughly trained, so it’ll be a long process to get the person I hire up to speed.
I’m looking forward to building a team around this business. Obviously, I worked for a large company during my PR days, but I’ve never built my own team before. You hear entrepreneurs talk all the time about how motivating and inspirational it is to build something yourself, and while I don’t necessarily know if I would call myself an entrepreneur so much as just a tutor who’s managed to find some success, the idea of building a team and expanding my services is really exciting for me.
I now work with students all around the U.S. and from around the world. Over half of my clients come from outside of Washington state. That is fundamentally motivating for me, to think I’m able to meet these people from all over, learn all these stories and help students who are in other countries work through the international application system. That is exciting in a way that I haven’t felt in another job before.
I genuinely love working with these students on their personal statements. Most people are very stressed out by college essays. I am not at all. To be fair, it’s easier when you’re not the one writing it. But I love working with the kids on these essays. I never cease to be amazed by the thoughtfulness and insight that high school students can bring to these essays. We often think of them as people in development, but that’s not true at all. When you read these personal statements, you realize that they see the world in a different way than we do, and often it’s in a very rich and constructive way. The more students I get to work with, the more creative and inspiring stories I get to come across in the future, which I find to be enriching in my own life as well.
Related: I Turned My Side Hustle Into a Passive Income Stream That’s Earned More Than $1 Million — But Making Money Isn’t Even the Best Part
For anyone considering taking a tutoring side hustle full-time, my first piece of advice is pragmatic: Map out the finances. Use constructive negative thinking and assume that it won’t work, then ask yourself, What would happen if this totally crashed and burned? Do I have a backup option? Can I handle it financially for 10 to 12 months? Try to give yourself a cushion just in case.
I was part-time for six years before I transitioned to full-time, so when I made the leap, I was fairly confident I had enough support to make it happen. You have to suss out the environment to know if going full-time is really right for you.
Also, think critically about what working independently means. Often, we glorify independent work as a sense of freedom. You don’t have a boss. You don’t have performance reviews. You don’t have any externally imposed deadlines. The flip side of that is that everything is on you. If I’m going to generate a dollar of revenue, I have to go out and find it myself. If I make a mistake, there’s no one to shift blame onto, and I need to take responsibility. The safety rails are taken away, and for a lot of people, that doesn’t work. That’s not a commentary on their work ethic; it’s just not the style of work that they enjoy. For me, it is — I like that independence.
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