How Working Moms Are Discovering They Can Homeschool

Kerry McDonald | December 11, 2018

How Working Moms Are Discovering They Can Homeschool

"I would love to homeschool my kids, but I have to work.” Homeschooling parents hear this statement all the time, sometimes during casual conversations about various education options, or more often, when a friend or stranger confides that schooling isn’t working so well.

I’m not going to lie, homeschooling requires a lot of effort, presence, time, and vigilance. But with more parents able to work flexible schedules, share childrearing responsibilities, take advantage of the growing gig economy, and utilize various alternatives to school, homeschooling is becoming a more realistic option for many families.

The three moms spotlighted below have found that entrepreneurship is a particularly powerful tool for combining homeschooling, career fulfillment, and financial prosperity. They are strategic and savvy multi-taskers—just like most parents juggling work and family. But as entrepreneurs and homeschoolers, these moms show that it is possible to fully nurture your kids and your company at the same time.

Samantha Barnes has long celebrated the intersection of food, family, and education. After college, she worked as a public school teacher in Massachusetts and as a private school teacher in California and began on a whim to teach cooking classes to her middle school students. She gradually added other offerings on the side, like cooking-themed birthday parties and after-school classes. Samantha eventually left her teaching job to devote her full-time energies to her budding business, adding preschool programs and writing cooking curriculum for public and private schools throughout Los Angeles.

Samantha Barnes


Her business was booming but was logistically constrained to her immediate geographic area. She wondered how to grow. It was 2013, and subscription delivery boxes were gaining popularity. “This is it!” she said, realizing that mailing her recipes, culinary tools, activities, and lesson plans to interested families around the country would be the ideal way to scale her business offerings. Five years later, her company, Raddish, has over 20,000 monthly subscribers—about one-quarter of whom are homeschooling families. “We discovered early on that Raddish really appealed to homeschoolers,” says Samantha. In 2014, she attended her first homeschool conference as a vendor. “I didn’t know much about homeschooling,” she recalls. But a few years later when school wasn’t working out for her own child, homeschooling seemed like a reasonable path. “My daughter went to a Montessori school first,” says Samantha, “but then she went to first grade in a public school and had a terrible year. We knew we had to make a change.”

Samantha discovered an innovative charter school near her home that would be the perfect fit for her daughter, followed by her younger son. The children attend the school two days a week, where they focus on project-based learning, and they are at home for the remaining three days. Samantha’s kids are in a Da Vinci school, a hybrid homeschool/public charter school model rapidly expanding across California. A recent article at Forbes describes Da Vinci’s appeal to parents, many of whom never expected to homeschool: “Despite what one might consider a common homeschool family unit (two parents and one who is able to not work and stay at home), many Da Vinci Connect families do not fit that mold and are finding unique ways to make the homeschool option work for them.”

This hybrid charter school, combined with an array of classes for homeschoolers throughout the week, enables Samantha to build her business and practice what she preaches: making space for family and cultivating a nourishing home. “I think so much of the journey for us has been unlearning everything we ever learned about education up to this point in our lives,” says Samantha. “In my heart, I believe that there will be a dramatic shift in education in our country in the next 20 years, and we are just at the beginning of it.”

Shaylanna Graham is a lifelong entrepreneur. She fell in love with business at an early age, majored in it at college, and launched several successful companies. Soon after her son was born, she decided to scale back her work and focus on him and, later, his younger sister, gravitating early on to homeschooling. “My husband and I believe in the inherent right to freedom and free will for all humans, including children. Freedom is the main reason why we chose to homeschool. We passionately believe that children should be free to follow their own passions and interests. They should have the freedom to direct their own learning,” says Shaylanna, who gravitates toward unschooling, or a self-directed style of education for her children.

Freedom is also the primary inspiration for her business. Despite being a busy homeschooling mom, she felt the entrepreneurial itch and wanted to feed her passion for business. Now, Shaylanna runs a coaching business to help women achieve financial independence and maximize their creative potential through entrepreneurship. “I started my business because I managed to create a lifestyle of freedom for myself, but I witnessed other moms—especially homeschooling moms—struggling financially, feeling overwhelmed, wanting to travel with their children, and wanting to have more freedom in their own lives,” she says. “I am passionate about helping women to realize their financial goals through entrepreneurship.”

Shaylanna Graham


The flexibility of homeschooling and entrepreneurship allows Shaylanna and her family to travel frequently from their Boston home, immerse the children in new cultures and experiences, and let them follow their interests. Organization is the top priority, she says, in successfully managing homeschooling and growing a business. A support system is also key. Shaylanna cites the support of her husband and family and the resources of two local self-directed learning centers that her older son attends part-time.

Much of Shaylanna’s satisfaction comes from watching women discover that they really have skills and talents to share with others and can showcase these qualities through entrepreneurship. “It feels so rewarding to watch my clients go through such life transformations and create a lifestyle of freedom for themselves and their families,” she says.

Working in a conventional corporate job, Nina Litovsky dreamed of starting her own business. In 2008, pregnant with her first child, she decided it was the right time to give up the 9-to-5 job and devote her energy to parenting and entrepreneurship. Ten years and four children later, Nina’s high-end custom web design business for medical professionals is flourishing. Nina Interactive grew from a small side business as a new mom to a company that now employs several web developers and serves a multitude of clients. “Entrepreneurship is one of my core values,” says Nina. “To me, it’s all about taking control of your life. It’s about empowerment and financial independence. It’s about helping others.”

While running her Florida-based business, Nina also homeschools her four young children. She and her husband, who is also an entrepreneur, wanted to give them the freedom to pursue their own passions and develop their talents outside of a conventional classroom. Nina explains:

We unschool. I don’t think we would have had the time and ability to run a business and do parent-directed homeschooling (school-at-home where the parent is the teacher). But even if I didn’t run a business I would have unschooled, anyway. Unschooling/self-directed learning is the homeschooling option that aligns with my values.

Her children learn from the people, places, and things around them, in pursuit of their own interests and supported by their parents. The flexibility of entrepreneurship allows Nina to take her children to interesting activities and events, engage in lengthy discussions on a variety of topics, read books and watch movies and YouTube videos together, and visit museums and the ocean often.

Nina Litovsky


The ability to adapt to changing work demands and family needs has been an important factor in Nina’s success, as have the skills of multi-tasking and maximizing those quiet moments when the baby sleeps or the kids are playing. Her husband is also a supportive partner, and she delegates tasks where she can. “For a long time, we didn’t have any ongoing external help with the kids,” says Nina. “Only recently have we hired a part-time babysitter, which of course makes it easier for me. We also recently started hiring cleaning help almost every day, which frees up more of my time.”

For Nina, unschooling and entrepreneurship are a good match. They offer freedom and flexibility for both the adults and children, and they also encourage a self-directed, self-reliant mindset. “I want to inspire my kids to be entrepreneurs,” says Nina, “so I hope they learn by observing me.”

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This article has been republished with permission from Foundation for Economic Education.