A Tough Decision: Leaving a Full-Time Job for Passion

Carter Osborne spent two months agonizing over whether to leave his full-time job and fully commit to his tutoring side hustle. For five years, he balanced both roles, dedicating evenings and weekends to editing college admissions essays for high school seniors.

In August 2023, Osborne faced a turning point. He was promoted to director at his public relations firm, a role that came with increased responsibilities. At the same time, his side hustle had grown so significantly that he was working a grueling 70 hours per week between the two jobs. His tutoring business alone earned him more than $114,000 in 2022, effectively doubling his PR salary.

By November, Osborne began exploring new full-time opportunities but found himself uninspired. None of the roles he considered matched the passion and fulfillment he experienced in tutoring.

Then, one of his students achieved acceptance into their dream school: Pitzer College, a private liberal arts institution in California. The moment solidified Osborne’s decision. “Tutoring would become my full-time job,” says Osborne, 29.

In January 2024, Osborne left the PR firm, and the results were immediate. With increased availability, he quickly ramped up his client list. While the spring season is typically slower for college admissions tutoring, Osborne already boasts 24 clients, compared to just nine during the same time last year.

From Side Hustle to Thriving Business

Osborne began his tutoring journey in 2017 as a graduate student looking to earn a little extra money. With a mentor’s guidance and referrals, his business grew steadily through word-of-mouth recommendations.

By 2023, demand for his services had skyrocketed. The lingering effects of the pandemic left many students struggling with the increased demands of college essays. More students are applying to college than ever, and many now face writing upwards of 20 essays when applying to multiple schools.

Osborne worked with 52 clients in 2022 but had to turn some away due to overwhelming demand. To manage his workload, he’s already considering expanding his business by hiring another tutor or broadening his services to assist graduate school applicants, transfer students, and even younger students applying to middle and high schools.

Currently, Osborne spends about three hours per week refining his approach, researching essay trends, and developing new services. By summer’s end, he anticipates ramping up to 40 hours per week — or even more during the busy fall season.

Navigating the Financial Leap

Taking a side hustle full-time comes with financial uncertainties, but Osborne approached the transition with careful planning. Before quitting his PR job, he calculated six months’ worth of expenses, covering his mortgage, business insurance, and average spending. With a solid financial cushion in place, he felt confident moving forward.

Now, with more flexibility, Osborne uses his extra time to focus on self-care. He’s exercising more, walking his dog, and spending time with family. The freedom to step back and relax has made the leap into entrepreneurship even more rewarding.

“I had the money for vacations and travel last year, but no time to do it,” says Osborne. “What good was it? Now, I can control the scope and growth of my business, and that’s been incredibly freeing.”

Thinking of taking your side hustle full-time? Osborne’s story is a testament to the power of planning, passion, and perseverance.