Carter Osborne

Carter Osborne started a college essay tutoring side hustle in 2017 and grew it from $58,000 to $114,250 annually before taking it full-time in 2024. In his first year as a full-time tutor, he earned $222,000 working with 66 clients, nearly doubling his previous annual earnings.

Carter runs a college essay consulting business helping high school students with their college application essays. The business is highly seasonal, with 80% of revenue generated between July and December during college application season. He works with students from around the U.S. and internationally, charging premium rates for personalized essay coaching and editing services.

• The business grew exponentially from 37 clients and $58,000 revenue in 2020 to 66 clients and $222,000 in 2024
• Revenue is highly seasonal with 80% earned between July-December during college application deadlines
• Work schedule varies dramatically from 10-15 hours per week in off-season to 50-70 hours during busy months
• The transition from side hustle to full-time nearly doubled annual earnings in the first year

• Referrals are the primary growth driver - parents rely on word-of-mouth recommendations for high-stakes college admissions consulting
• Industry demand exceeds supply of qualified professionals, leading to consistent bookings
• Building relationships with other consultants who refer overflow clients
• Raising rates when transitioning to full-time to maximize revenue potential

• Balancing two full-time jobs during busy season before making the transition
• Managing increased administrative workflow including emails, scheduling, billing, and client onboarding
• Building systems to handle larger client volume efficiently
• Taking on all responsibility for revenue generation and business operations without safety nets

• Map out finances carefully and use constructive negative thinking - assume it won't work and plan for 10-12 months of cushion
• Assess the environment to determine if going full-time is right for your specific situation
• Think critically about what independent work means - everything is on you including revenue generation and taking responsibility for mistakes
• Understand that independent work requires self-motivation and isn't suitable for everyone's work style