29-year-old's side hustle made $114,000 a year, so he quit his full-time job: I'm more successful and I work less

Carter Osborne left his full-time public relations job for his tutoring side hustle

Carter Osborne spent two months agonizing over whether to leave his full-time job for his tutoring side hustle.

He did both jobs simultaneously for five years. But in August 2023, he was promoted to director at his public relations firm, giving him more responsibility. At the same time, his side hustle — editing high school seniors’ college admissions essays — had grown large enough that between the two gigs, he was working 70 hours per week, he says.

The side gig netted him more than $114,000 last year, according to documents reviewed by CNBC Make It — effectively doubling his salary, he says. By that November, he was looking for a new full-time job — and realized none of his options had “that deep, passionate, resonate feeling that education has,'” says Osborne, 29.

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Then, one of his tutoring students was accepted to his first-choice school: Pitzer College, a private liberal arts college in Claremont, California. Osborne was so elated that he paced around his living room for several minutes, frantically texting the student his congratulations, he says.

Decision made: Tutoring would become his full-time job. Osborne left the PR firm in January, and is already finding that with more availability, he can take on more clients. Despite spring being a slow season for college admission tutoring, he already has 24 clients on his roster, he says. This time last year, he had just nine.

“I’ve found more success, and frankly, more love for the craft,” says Osborne.

Transitioning a side hustle into a full-time business

Osborne started his side hustle as a graduate student in 2017, hoping to make a little extra money. He had a mentor — someone he’d consulted when applying to schools himself, four years prior — who referred him some clients.

The business “snowballed” from there, growing almost exclusively by word of mouth, Osborne told Make It in August.

Currently, he’s working three hours per week, he says — researching essay trends, admissions stats and developing new tutoring services. That could ramp up to at least 40 hours per week by the end of the summer, and possibly more this coming fall.

That’s because demand for tutors is high: Last year, Osborne worked with 52 clients and had to turn others away, he says. More people are applying to college than ever before, and students are struggling with their essays more post-Covid than they used to.

Even for the most well-equipped applicants, applying for college is an “extraordinary workload,” Osborne says. When he applied for college in 2013, he wrote five or six essays. Now, many students applying to multiple schools are required to write upwards of 20, he says.

If demand rises enough, Osborne might hire another tutor — possibly a part-time contractor — to help with the workload, he says. He could also expand his business’ services: Other types of students also write admissions essays, from transfers and graduate school applicants to children hoping to get into their middle school or high school of choice.

Navigating financial unknowns

Osborne doesn’t quite know how to project a full year’s earnings yet, since the bulk of his business’ revenue comes in the second half of each year.

Before leaving his full-time job, he calculated his next six months of his household expenses — including his mortgage, business insurance and average weekly spending — and found enough of a “financial cushion” in his savings to cover it, he says.

In the meantime, Osborne is mostly using his offseason free time to exercise more, walk his dog and visit his parents more often, he says. Simply having the freedom to unplug makes him feel less stressed about taking his side hustle full time, he adds.

“I had the money for [vacation and travel last year], but no time to do it,” says Osborne. “So, what good was it? … It’s been very freeing to me to be able to control the scope and the growth of my business.”

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