You’re sitting at your desk, scrolling through job listings again. The familiar weight of wanting something more, but uncertain if your skills could translate into something bigger.
Kerry Komarov knows this feeling well. After a decade of teaching middle school reading, she found herself wondering if her classroom expertise could transform into a business. Like many considering this leap, the path wasn’t immediately clear—until her maternity leave with her second son opened new possibilities.
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The Turning Point
The Peppa Pig theme song plays in the background as Kerry manages her virtual services business. Three-quarters of her clients live in different states, while she works surrounded by toys and two energetic boys who love to wrestle. “I run my business out of my house! And specifically, I usually run a business on the floor of my kids’ playroom… Honestly, I wouldn’t want it any other way! They are my ‘why,'” she shares.

This wasn’t where she pictured herself during her ten years teaching English and Language Arts. Each day, she managed 130 students, created multiple presentations, graded assignments, and handled parent communications. These tasks seemed specific to education—until she looked closer.
When Kerry welcomed her second son on September 3, 2023, she didn’t realize he would become the catalyst for her career transformation. She made a strategic decision to extend her maternity leave as long as her teaching contract would allow—a full school year—keeping her options open while exploring new possibilities.
“I started this whole freelance gig when my second son was just two months old,” Kerry explains. This period gave her the space to give entrepreneurship her “absolute best effort” while maintaining the security of potentially returning to teaching if needed.
Building Something New
Kerry approached her business launch with a unique perspective: while she might have been new to entrepreneurship, she wasn’t new to the skills she’d be offering. “When I first started, I knew that I was a ‘beginner’ in the business world, but I was NOT a beginner in terms of the tasks that I was doing for people. In fact, I had 10 professional years of doing these things.”
This confidence helped her price her services appropriately from the start, positioning herself above entry-level rates to reflect her decade of professional experience. Her teaching background equipped her with both tangible and intangible skills that proved invaluable in her new role as a business owner.
Kerry’s approach to business has been refreshingly straightforward. She keeps operations lean, utilizing free versions of essential tools like Google Suite, Canva, Calendly, and social media platforms. This zero-overhead strategy allows her to focus on growth without financial pressure.
Her marketing strategy centers on maintaining what she calls a “stalkable” presence on Facebook, posting at least weekly to showcase her capabilities and share client testimonials. “This way I stay in the mix,” she explains, “and when I apply to job postings, or when I send a cold pitch, and people inevitably look me up, they have things to look at.”
This approach paid off with her very first client. “Looking back, I think our first call was actually an onboarding call,” she recalls. “By the time we got on a call, I think we just clicked in terms of personality, and she liked the experience I brought to the table. Just goes to show that all my personal promoting and consistency in posting paid off.”
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Finding Balance
Today, Kerry’s schedule revolves around her family’s needs. She concentrates her work on Tuesdays and Fridays when her mother helps with childcare, fitting other tasks around preschool schedules, park visits, and library trips. This flexibility stands in stark contrast to her teaching days of rigid schedules.
To combat the potential isolation of working from home, she maintains an active social life, organizing playdates with other local moms and scheduling gatherings with friends who are in similar life stages. “I am very much okay with the peace of not being surrounded by hundreds of middle schoolers a day,” she jokes, “though there is nothing really peaceful about 2 little boys, but it’s different when they are yours.”
One of the most valuable pieces of advice came from her husband early in her journey: “You make the rules.” This simple reminder helped shape her approach to business ownership, allowing her to create a structure that works for her family’s unique needs.
Your Path Forward
Kerry’s journey demonstrates how existing professional skills can open unexpected doors. Whether you’re a teacher, like Kerry, or working in another field, your daily tasks and experiences are building blocks for potential entrepreneurship.
The floor of a playroom might not seem like a typical business headquarters, but Kerry’s story shows that success doesn’t require a conventional setup. What matters most is recognizing the value in your existing expertise and being willing to take that first step from a place of strength rather than uncertainty.
Got an awesome startup story? We’d love to hear how you turned your big idea into reality! StartUp101 is all about sharing real stories from founders like you to inspire others who are just getting started.