For years, Jenna Dee showed up every day for her students with everything she had to give. She loved helping kids who were on the edge of dropping out find a path forward, but the demands of teaching eventually caught up with her. Between long commutes, endless grading, and the emotional weight of the job, she found herself coming home drained and missing the moments she most wanted with her husband and kids.
After her daughter was born during COVID, the burnout hit hard—and Jenna knew something had to change. That decision led her down a new path, one that would take her from the classroom to home with her family where she replaced her income with freelancing in just six months.
And the best part? She’s traded burnout for balance and created a business that works for her life—not the other way around.
The Leap Into Freelancing
At first, Jenna thought she would just take a short unpaid leave when her daughter started school. But during her summer break, she stumbled across the Live Free Academy (thank you, Instagram algorithms!) and decided to give freelancing a shot.
Even though investing in the program felt scary, Jenna had support from her husband (an entrepreneur himself) and her parents, who believed in her.
Within weeks, she had completed her portfolio and landed her very first client—a wedding makeup artist she’d known for years—before she even finished the course.
From there, things snowballed:
She found her second client through the LFA job leads board.
She picked up her third client at a local networking event.
She signed her biggest client—a social media management package—just a few months later.
By the end of six months, Jenna had six clients and was close to hitting her monthly income goals.
Life Now as a Freelancer
The biggest win for Jenna hasn’t just been the money (although she’s proud of that too!). It’s the freedom and presence she has now with her family.
She no longer spends her evenings grading papers or collapsing on the couch exhausted. Instead, her afternoons are spent at the park, helping with homework, or just being present without the constant stress of the classroom hanging over her head.
Jenna sets her own hours, works with clients she truly enjoys, and has the space to say “yes” to the things that matter most—whether that’s volunteering at her son’s school, taking a midweek trip with her daughter, or simply having dinner together as a family every night.
And perhaps the sweetest part? Her kids notice the difference. Her son no longer associates “mom with her hair up in a bun” as being stressed and unavailable. Instead, he sees a mom who is smiling, calm, and there for him.
Jenna says, “This business has given me back my joy. I get to use my skills, provide for my family, and actually enjoy life again.”
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What We Can Learn from Jenna’s Story
Jenna’s journey is a reminder that change is possible—even when it feels scary. She didn’t have it all figured out when she stepped away from teaching, but she took one small step at a time and trusted the process. By leaning into her transferable skills, seeking out support, and staying consistent, she built a business that gives her both freedom and stability. Whether you’re feeling stuck in a job that drains you or simply longing for more time with your family, Jenna’s story shows that with courage, commitment, and the right resources, you can create a life and business you love too.
Start today by identifying one skill you already have that could be the foundation for a freelance business, and take one small step toward putting it into action—whether that’s reaching out to a potential client, setting up a portfolio, or signing up for a course that will guide you.
You got this.
The Live Free Academy
If you have read Jenna’s story and feel inspired to learn more about freelancing and how it can help you make a flexible, stable income from home. Please reach out, and ask me any questions about getting started or what it could look like for you to become a freelancer!
Send me a message on Instagram @micala.quinn, I’m happy to chat through that with you!
As always, if you want to become a freelancer and are ready to get started, the most hands-on way I can help you is through my program, The Live Free Academy!
LFA will walk you through the exact steps to build your business and land clients. There are templates and tools to help you implement every step of the process. Plus, it comes with my trifecta of support–weekly coaching calls with me, monthly challenges to help you land clients, and the student community to connect with and build relationships with other women building their businesses!
There are job leads and skills training in the top freelance services businesses are hiring for as well. Sign up for The Live Free Academy course here!
