The Homeschool How To

I’m re-releasing this episode because it’s still one of my all-time favorites—and honestly, one of the conversations that stayed with me long after we hit stop on the recording. 

In this episode, I’m joined by Kiri Jorgensen, a former public school teacher in rural Montana and mom of four. Kiri shares what she saw changing inside the school system—from Common Core and high-stakes testing to increasing bureaucracy—and why her family ...

A former public school teacher never planned to homeschool — until COVID forced a hard reset. In this episode, Cheryl talks with Janae Daniels from the School to Homeschool Podcast about the moment everything changed: the “magical” 2020 shutdown, the surprising nudge to homeschool, and the first day that completely fell apart… until a piano tuner accidentally delivered the best real-life science lesson her kids had ever experienced...

You’ve heard it a thousand times: “But what about socialization?” “What if my kid falls behind?” “What if they only want screens?”
In this episode, I’m joined by Courtney (former teacher + school psychologist, now a private evaluator/advocate) to break down what unschooling actually is — and what it looks like in real life.

We talk about the fear parents carry when they step outside the school system, and why so many families n...

What happens when you stop accepting the “official story” and start asking better questions—about education, parenting, freedom, and the systems we’ve all been told to trust?

In this week’s episode of The Homeschool How To Podcast, I’m joined by Tim (ANCAPTim)—a homeschooling dad, songwriter, and outspoken advocate of voluntary exchange, individual responsibility, and a truly free market. We talk about what anarcho-capitalism means ...

What happens when a homeschooled kid grows up, skips the “missing out” narrative, and builds a real community of motivated teens who want to create, lead, and launch?

In this episode of The Homeschool How To Podcast, I’m joined by Malcolm—a homeschooled graduate who spent years in Classical Conversations (CC) and is now the founder of Teen Mastermind, a fast-growing entrepreneurship community for teens that’s already reaching beyond...

You know your child better than any teacher, curriculum, or system ever could — but trusting that instinct can feel scary.

In this episode of The Homeschool How To Podcast, I’m joined by Leanne, a former classroom teacher, homeschool mom of two grown kids, and Unfold History co-creator, to talk honestly about what homeschooling really looks like over the long haul.

We dive into:

• How to know when a curriculum isn’t working — and wh...

What if one of the biggest homeschooling wins isn’t curriculum… but protecting your kids from modern pressures and modern “food”?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Patrick & Ashley—homeschool-connected entrepreneurs and the team behind Jigsaw Health—to talk about:

• Patrick’s experience being homeschooled in 7th–9th grade (and why it mattered)
• The myth of “socialization” vs. what homeschool ...

Homeschooling isn’t just about math lessons and reading charts—it’s about who gets to shape how your kids see the world.

In this episode, I’m joined by Dr. Jonathan Newman from the Mises Institute, a homeschooling dad, economist, and libertarian who breaks down why he and his wife chose to keep their kids out of government schools, how they approach reading and “adulting” skills at home, and why there’s really no such thing as a “ne...

What happens when vaccine mandates, school regulations, and a mama’s intuition collide? In this episode, I sit down with Tiffany, a homeschool mom of almost-seven-year-old twin boys in West Virginia and an occupational therapist who now serves the homeschool community.

Tiffany shares how COVID, vaccine requirements, and a strong Christian conviction opened the door to homeschooling—not just for her twin boys, but for her stepkids to...

In this episode, I’m joined by Jem from Australia, a homeschooling mom of four navigating autism, ADHD, sensory needs, school refusal, and neurodivergent learning—and doing it all with honesty, humor, and so much heart.

Jem shares why her family left the traditional school system, how her kids went from daily meltdowns and sensory overwhelm to peaceful mornings and learning at their own pace, and why unschooling naturally became the...

In this powerful episode, Cheryl sits down with Anya, a seasoned mom who made the courageous choice to pull her son out of school during a season of deep grief — and discovered that unschooling was the unexpected key to his healing, growth, and confidence.

Anya shares how losing her son’s father, navigating the chaos of COVID schooling, and tuning into her child’s emotional needs led her to take full ownership of her family’s educat...

Discover how one family's challenging school experience became a powerful homeschooling journey. What starts as a two-week trial becomes a wake-up call that changes everything. This raw, honest conversation reveals why traditional school wasn't working and how unschooling created the freedom their family desperately needed.

In this episode, we explore:

• The wake-up call that changed everything about their education appro...

Is your child struggling with ADHD, allergies, or chronic illness? Wondering why childhood health is declining despite modern medicine?

In this episode, functional medicine doctor Dr. Dusty Hess explains the root causes behind rising rates of ADHD, autism, and infertility—and shares practical solutions every family can implement today.

What You'll Learn: ✅ Functional medicine vs. conventional healthcare (firefighters vs. builder...

What happens when you ditch the American Dream, move onto a boat with five kids, and homeschool while traveling the Caribbean? In this inspiring episode, former public school teacher Tanya shares her family's extraordinary journey of "boat schooling" for nearly a decade.

From their catamaran "Take Two" in Florida's 10,000 Islands, Tanya opens up about:

Why They Left Conventional Life Behind

• The "...

Nicole Goff was homeschooled by "hippie" parents, tried public school for two years (8th-9th grade), excelled academically but faced bullying, and chose to return home. Now she's homeschooled five kids for 20+ years and runs Four Corners Community School—a 32-family cooperative in Florida.

What we cover:

• Florida's PEP scholarship: $8,000 per homeschool child for tutoring, curriculum, sports, music lessons, and...

Discover how former UK teacher Kate transformed 24 years of mainstream education experience into "The Hive Adventure" - a revolutionary barefoot unschool in the Dominican Republic. In this inspiring episode, Kate shares her journey from French grammar teacher to creating a human-centered learning environment where students grow their own food, tackle global sustainability challenges, and learn emotional regulation from th...

Ready to see what homeschooling looks like from kindergarten through 12th grade? In this episode, Cheryl interviews CJ, a veteran homeschool mom who's been teaching her three kids at home for over 12 years and is now preparing for her first graduation!

In this episode, you'll discover:

• How to transition from elementary to high school homeschooling with confidence
• Creating transcripts and meeting college requirements with...

Discover how one mom transformed her family's life by leaving traditional school behind for homeschooling on a 30-acre farm. In this inspiring episode, Brooke shares her journey from suburban Long Island to rural farm life, and why she chose to pull all five of her kids from conventional school.

What You'll Learn:

• How COVID sparked a complete lifestyle change and homeschool journey
• Why common core curriculum pushed one f...

Join us for an inspiring conversation with Jessica Waldock, Florida homeschooling mom and founder of The Waldock Way, as she shares her 8-year journey homeschooling her only child.

In this episode, we explore:

• How to successfully homeschool an only child without feeling isolated
• Overcoming the "socialization" question and finding community
• Creating flexible daily routines that work for one child
• Interest-led learning and u...