The Homeschool How To

Are you constantly wondering...

"Am I doing enough?"

It's one of the biggest fears homeschool parents carry—and after nearly 30 years homeschooling seven children, Jennifer Pepito has a very different perspective.

In this episode, Jennifer shares why perfect homeschool days aren't the goal, why family connection matters more than checking every academic box, and how her oldest daughter—despite what she describes as an "imp...

Two former public school teachers — and twin sisters — pull back the curtain on what really happens in a classroom of 25+ kids, including the one statistic that will change how you think about homeschooling forever. Kathy and Melissa share why they left teaching to homeschool their own children, why neither of them ever finished a curriculum in 30 years in the classroom, and how they turned the science of reading into a...

Rapkat was born in northwest China, fled to Malaysia at five, landed in Brooklyn, bounced through public, private, and charter school, married at seventeen, attended a coding bootcamp, got a remote software engineering job — and has been homeschooling and world schooling his five kids across Europe and Asia ever since.

In this episode we talk about why he thinks getting straight A's is actually not a good sign, what "learning ...

What happens when two parents with a 70-acre property, a wedding venue, and a 2% chance of having children decide the local school system just isn't good enough for their girls? They build something better from scratch.

In this episode, Cheryl sits down with Sarah and Greg Holland of Jericho Valley Co-op in Berkshire County, Massachusetts — a homeschool support organization they built on their own property, with a licensed tea...

What if the problems in public school weren't accidents? What if low literacy rates, changing math standards, social emotional learning, and ideological curriculum were all part of a plan that started over a hundred years ago?

This week Cheryl sits down with Nicki Truesdell — a second generation homeschooler who has been in the homeschool world since 1983 and has been homeschooling her own five kids since the year 2000. Nicki ...

What does it actually look like to homeschool five kids across wildly different ages — while running a business, managing a rambunctious toddler, and doing it all on one income?

This week I'm joined by Amanda, a homeschool mom of five from St. Augustine, Florida. Amanda started homeschooling when her family left Germany in 2020 — one week before the world shut down. What felt like a leap of faith turned out to be...

Elyse Scheeler spent years inside the public school system as a speech language pathologist. She had a classroom full of kids making real, measurable progress. The district shut it down — not because anything was wrong, but because her program made their compliance numbers look bad.

That's when she knew she had to leave.

In this episode Elyse pulls back the curtain on what school staff see every single day but a...

What happens when someone who hated being homeschooled grows up and chooses to homeschool his own children anyway?

In this deeply honest conversation, Logan Hufford shares what homeschooling looked like growing up in a large family in the 90s, why he resented parts of it for years, and what he’s doing differently with his own kids today.

We also talk about something many parents are afraid to discuss openly: what children are b...

What happens when life completely falls apart — and you still have to show up for your kids? This week Cheryl sits down with Barbara, a former special education teacher turned homeschool mom of four, who opens up about one of the hardest questions in homeschooling: what do you do when you're grieving?

After years of fighting the school system for resources her students deserved, Barbara knew she didn't want that for her own ki...

What happens when a single mom in the Foreign Service gets the double whammy — "your child might have dyslexia" AND profound hearing loss? She figures it out. Katharyn Havens joins Cheryl from outside Nairobi, Kenya, where she's running a multi-age homeschool pod, teaching kids AI ethics, and building her own AI co-pilot for homeschool parents.

In this episode:

• How cochlear implant surgery changed everything — and bou...

Most parents ask, “Can I homeschool if I still need to work?”

Laresia and her family didn’t just ask that question—they built a life that answers it.

In this episode, we talk about what happens when you choose homeschooling before you even become a parent, and how that decision shaped everything—from family connection to raising a child who is already thinking like an entrepreneur.

Their 9-year-old son is...

Last week, we heard why teachers are leaving the system. This week, meet one who did — and what she built instead.

Jen Delle Fave spent 8 years as a public school English teacher in upstate New York before walking away to raise her kids, homeschool, and build a real estate portfolio — without ever going to a bank. Now living in Florida with her husband and two kids (11 and 13), Jen runs multiple businesses, travels const...

What happens when a former public school teacher decides she won’t send her own kids to school?

In this episode of the Homeschool How To Podcast, Cheryl sits down with Ashley Martinez—a former teacher turned homeschooling mom of two—who shares what she saw inside the classroom, why she chose a different path, and how her family makes homeschooling and working actually work.

This conversation goes beyond curriculum a...

In this episode, we step outside the traditional conversation around education and take a deeper look at something bigger—how we’re raising our kids in today’s world.

Cheryl sits down with Doug Evans, founder of The Sprouting Company, to talk about self-sufficiency, food, environment, and why more families are questioning the systems we’ve always relied on—from school to the food we eat.

They explore:

What if the biggest problem with education isn’t your child… but the school system itself?

In this episode of the Homeschool How To Podcast, Cheryl sits down with Dr. Peter Gray, author of Free to Learn, to talk about what schools get fundamentally wrong about how children actually learn.

They discuss the hidden history of schooling, why shame and obedience are still built into the system, how kids learn to read and do m...

What if the problem isn’t your child—but the environment they’re expected to learn in?

In this episode, Cheryl talks with Corianda “Corey,” a homeschooling mom of six living in Spain, about raising neurodivergent kids and what happened when traditional school stopped working for her family. With three sons on the autism spectrum and experiences with ADHD, Corey began questioning whether the system was a...

In this episode of The Homeschool HowTo Podcast, Cheryl sits down with Stephany Rios — a homeschooling mom of five — to talk about building a business from home, navigating dyslexia, and learning to let go of school timelines.

Stephany shares:
 • The preschool bus moment that made homeschooling non-negotiable
 • Running a jewelry business while homeschooling
 • What to do when curriculum isn&rsquo...

What if the biggest education question isn’t “public vs. private”… but who is shaping your child’s worldview?

This week on The Homeschool How To Podcast, I’m joined by documentary filmmaker Spencer Taylor, creator of The Death of Recess (streaming on Angel Studios). Spencer shares what sparked the film—when his school eliminated recess—and how that change connected to a bigger story: ...

What happens when you stop measuring “success” by convenience—and start building your family life around your deepest values?

In this episode of The Homeschool How To Podcast, Cheryl sits down with homeschool dad Todd Marchand, founder of Be Whole Do Good, to talk about what it really looks like to raise kids with resilience, emotional tools, and a strong sense of identity—without turning your home into a lec...