Teen Bosses: How Young Entrepreneurs Are Balancing Business and High School

By Jay Jacobson, LUTCF, CPC, CFSP

In a quiet Iowa town, the owner of a local funeral home made an unconventional hiring decision that would quietly reshape the business. Instead of seeking out traditional applicants, he intentionally recruited the busiest, most active student-athletes in the community—young people juggling school, sports, clubs, and part-time jobs.

Why? Because experience had taught him that these were the individuals who thrived under pressure, needed little supervision, and understood time management better than most adults. They showed up, followed through, and brought energy into a workplace where sensitivity and professionalism were non-negotiable.

But the strategy did more than keep things running smoothly. These young hires became informal ambassadors for the business—sparking interest among their peers, increasing visibility among their families, and ultimately deepening community trust. Some even went on to pursue careers in funeral service themselves, creating a ripple effect that helped address a looming industry need: the recruitment of future professionals.

What began as a local hiring decision evolved into a long-term growth and succession strategy—and a model worth examining for other small business owners facing workforce challenges.

Now, years later, I’m observing that across the country, a growing number of teenagers are diving into entrepreneurship—launching lawn care companies, detailing cars, washing windows, repairing phones, offering tutoring, and even developing apps. These ambitious young people aren’t just picking up part-time jobs. They’re building businesses—and learning lessons that will last a lifetime.

Much like the hiring practice I utilized early in my career, these young entrepreneurs provide a tremendous stream of qualified, experienced business leaders for your organization.

“Whether it's mowing grass, detailing cars, washing windows, or providing IT support, young people are learning lifelong lessons and becoming their own boss.”  

Getting Started: The Spark Behind the Hustle

For many teen entrepreneurs, the journey starts with a simple idea and a willingness to try. Some see a neighborhood need—like unkempt lawns or dusty driveways—and turn it into an opportunity. Others follow their passions: a love for tech, a knack for design, or a desire to help others. What unites them is the decision to take action instead of waiting for permission.

“I started out mowing one neighbor’s yard,” said 16-year-old Miguel, who now manages a weekly schedule of ten clients. “Then word spread. I made a flyer, got some referrals, and it just kept growing.”

Obstacles and Growing Pains

Of course, starting a business as a teen isn’t without its challenges. Limited time, lack of transportation, and juggling schoolwork can all complicate operations.

“When I started offering computer support, I didn’t even have a car,” said Emily, 17. “I had to bike to clients’ homes with my laptop in my backpack. It wasn’t easy, but I wanted to prove I could do it.”

Many also mention the struggle of being taken seriously. “Some adults look at you like, ‘What do you know?’” Miguel said. “But once they see how professional you are, they come around.”

Balancing School, Work, and Life

Time management quickly becomes a critical skill. Teen entrepreneurs must navigate homework, sports, family expectations, and the demands of running a business.

“I work after school and on weekends,” said Jasmine, a 15-year-old who runs a window-washing service. “I also set limits. I won’t take new jobs during finals week, and I always leave time for my friends.”

Peer Reactions: Cheers and Challenges

While some teens get full support from their friends, others find that not everyone understands the hustle.

“Most of my friends think it’s cool,” said Evan, who designs websites for small businesses. “But a few think I’m missing out by not hanging out as much. I tell them this is my version of fun.”

Future Plans and Big Dreams

So, where do they go from here?

Some hope to turn their businesses into full-time careers. Others see their ventures as stepping stones—early experiments that teach them how to lead, communicate, and innovate.

“I’d love to major in business and scale what I’m doing now,” Emily said. “But even if I don’t stick with tech support forever, I know I’ve learned skills that will help me in anything.”

Support Systems: Behind Every Young Entrepreneur

Behind nearly every young business owner is a strong support system. Parents often provide transportation, encouragement, and even seed money for supplies or equipment.

“My parents were hesitant at first,” Jasmine admitted. “But once they saw how committed I was, they helped me get insured and even co-signed for some of my gear.”

Friends, mentors, and even school staff can also play a role. Some teens have leaned on business teachers, coaches, or community leaders for advice and motivation.

Responsibility Starts at Home

Interestingly, many of these teens still juggle typical household responsibilities—chores, caring for siblings, or part-time jobs — to help support their families.

“My parents always said, ‘Business is fine, but your room still needs to be clean,’” Evan laughed. “So yeah, I’ve learned balance.”

Hiring Others: A New Level of Leadership

A few teen entrepreneurs have grown large enough to hire friends or classmates, learning firsthand about leadership, payroll, and accountability.

“I have two friends who help me on big jobs,” Miguel said. “It’s weird being the boss, but I try to treat them like equals. We’re all learning.”

Conclusion: Young Minds, Big Impact

Today’s young entrepreneurs are proving that age is no barrier to ambition. With creativity, grit, and support, they’re shaping their futures and inspiring others to do the same. Whether they continue their current businesses or pursue new paths, one thing is certain: these teens are already ahead of the game.