The Homeschool How To

What do you do when the school waits until the night before the last day of school to tell you your child is failing — and it turns out they broke his own IEP to do it? 

Dr. Amy Moore joins Cheryl this week. She's a cognitive psychologist and former teacher who left the classroom to research why struggling kids kept getting missed. She's also raised three sons — now 27, 25, and 21 — all neurodivergent, all hom...

What if the best thing you could do for your homeschool is put the worksheet down?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Kaitlin Zara, former public school teacher, homeschool mom of two boys, and host of the Homeschool Connections podcast, to talk about what she saw from the inside of a classroom that changed how she teaches her own kids now.

In this episode, you'll learn:

• Why Kaitlin had to unle...

What if the biggest thing standing between you and homeschooling isn't your ability...it's your belief that you have to get everything right?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Chad Hufford, homeschool graduate, father of six, biochemist, financial advisor, and speaker, to talk about what homeschooling looked like in the 1980s versus today—and why parents don't need to have all the answers ...

When Ali Johnson’s teenage daughter started saying she didn’t want to go to school, Ali initially thought she was dealing with normal middle school conflict.

Then everything changed.

After a serious accusation from two students, the school required Ali’s daughter to undergo an outside evaluation before returning to class. Even after she was cleared to return, administrators continued pushing the family toward additi...

What happens when you've built everything you thought you wanted... and realize it's no longer the life you want?

In this episode, I sit down with Ceci Washington, entrepreneur, business mentor, and homeschooling mom, to talk about the decision to walk away from a thriving business, leave behind financial security, and choose a completely different path for her family.

We discuss the fears that stop parents from homeschooling, why so...

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: