The Homeschool How To

What makes someone with a doctorate in education decide to homeschool her own children? And why would an education researcher who understands the concerns around screen time choose online curriculum for her kids?

Those are just two of the questions I get into with Dr. Kelly Cagle, former high school teacher, education researcher, homeschooling mom of three boys, and host of the Parenting IQ podcast.

Kelly didn't originally set out to homeschool. Four years ago, her oldest son's soccer training schedule made their previous school arrangement impossible. What started as a practical decision turned into...

What if the reason your homeschool days feel chaotic isn’t your curriculum, your kids, or you, but the belief that because you’re home, you should be able to do it all?

This week I sat down with Luke and Liss Hammond, parents of four who homeschool on a farm in rural southeast Missouri. Liss was homeschooled in the ’90s, one of eight kids, and she’ll be the first to tell you she resented her parents for it as a teenager. Then she went to college on a volleyball scholarship, earned a master’s degree, worked as...

What if your kid's math class was the stock market?

Robert Grego pulled his 15-year-old son out of public school three days before 9th grade. He had no plan. So he asked his son what he actually liked, and built the year around it: Latin because he loves the Roman Empire, American and military history because he's obsessed with World War I, and no Shakespeare.

This year, his son's math is a YouTube channel the two of them run together called The Hostile Takeover. They break down stocks, read charts and solve for X with...

Her son could recite Goodnight Moon word for word at two years old, but he couldn't learn his letter names. He couldn't rhyme. He could read "redeemer" in scripture but not "an."

Liz from Idaho never planned to homeschool. Her husband wasn't sold on it either, so they made a deal: try kindergarten at home for a year, and if it didn't work, he'd go to school. After that year, her husband became the biggest homeschool advocate in the house.

Then came the reading. Five reading curriculums. Every Orton-Gillingham program she could find. Speech therapy...

What if you're homeschooling your child and you're constantly wondering, Am I doing enough?

What if they're not reading yet? What if you didn't get through all five subjects this week? What if your child spent most of the day playing, helping around the house, going outside, asking questions—and you still feel like you didn't “do school”?

That's exactly the kind of pressure we talk about in this episode.

My guest, Kiely Modiri, spent 10 years working in public education. She earned a master's in educational leadership, was on the path toward...

What if your child isn't reading when you thought they would? What if they're not keeping up with the curriculum? What if you're starting to wonder whether you're actually doing enough?

That's exactly where this conversation goes.

Becky from Homeschooling Olympians homeschooled her five sons for more than 25 years. And one of those sons didn't learn to read until he was 10.

Instead of giving up on homeschooling, Becky learned to look at education very differently.

In this episode, we talk about the pressure homeschool parents feel to follow grade levels, check...

My guests this week, Owen and Christina, have five kids—and their family's answer to that question took them much farther than they ever expected.

It started with something surprisingly simple: their son wanted another thing.. "to be happy."

Around the same time, Christina watched a video about families who didn't have access to clean water.

So Owen and Christina did something most of us would probably never consider.

They shut off the water in their house.

For 10 days, their family walked to collect water, carried it home, washed cl...

What does your child actually need to learn—and how much formal homeschooling do they really need?

When I started The Homeschool How To Podcast, I wasn't even sure I was going to homeschool my own kids. I had a lot of the same fears so many parents have: Would my kids miss out? Would they have friends? Would they fall behind? Would I actually be capable of educating them?

More than 200 homeschool family interviews later, I've changed my mind about a LOT.

In this episode, I'm sharing what I've learned about homeschooling, so...

Her son was all set to graduate from her homeschool and become a master mechanic — and then he enlisted in the Marines a month before he turned 18.

Christina Franco from Rooted Home Life joins Cheryl this week. She's a former public and private school teacher turned homeschool mom of five, and she gets real about the moment she realized it wasn't public school she had a problem with — it was school itself. They talk about her oldest son's surprise decision to join the Marines, the "mother's intuition" story from speaker Amber O'Neill Johnston that changed how Christina pare...

What happens when a former public school teacher sells everything to homeschool from a bus?

Three years after her first appearance on the podcast, Jennifer Gossett is back with an incredible update.

Since we last spoke, her family has traveled to 47 states, sold the bus, bought a home, and discovered that homeschooling doesn't have to fit inside one box.

In this episode we discuss:

• Why she left public education
 • What roadschooling really looked like day to day
 • Why they decided to stop living on the bus
...

Can you really homeschool while traveling the world? What if homeschooling was actually illegal where you lived?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Stacy, a homeschooling mom, worldschooler, and resilience coach whose family made the life-changing decision to leave Germany after discovering homeschooling wasn't legally allowed there.

Today, their family travels throughout Europe while homeschooling their three children through a blend of worldschooling, roadschooling, self-directed learning, and unschooling. They share what daily life really looks like, how they afford long-term travel, why they chose this lifestyle, and what...

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 homeschooled differently based on what they actually needed. 

They get into the real story behind pulling her oldest out of school in 6th grade af...

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:

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 before they begin. 

Chad shares how his mom openly admitted she was figuring homeschooling out as she went, yet still raised chi...

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 additional outside services and requested permission to communicate directly with those providers.

Meanwhile, the bullying that started the entire situation continued.

In this episode of The Homesc...

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 many families feel pulled toward a different way of raising their children, the grief that can come with leaving your old life behind, and why...

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 "imperfect" homeschool experience—graduated summa cum laude, earned her law degree, and was preparing to take the bar exam.

We also discuss:

• Why many chi...

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 play-based system any parent can teach — no degree required. We cover special needs reading struggles, when to pull kids out (and when to put them back in), navigating SEL and ge...

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 to learn" means and why it matters more than any subject, how he intentionally teaches his kids to let go of possessions every time they move, and wh...

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 teacher who walked away from 25 years in the public school system because she believed in what they were building.

Sarah and Greg share how they went from ne...

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 is the author of Anyone Can Homeschool and Home Sweet Homeschool, and runs Knowledge Keeper's Bookstore where she reprints rare out-of-print American history books to get the real story ba...

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 the best thing she ever did.

We talk about:
→ Why Amanda and her husband felt called to homeschool even before COVID
→ What it's rea...

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 aren't allowed to say out loud. She couldn't tell parents what she suspected. She couldn't refer kids to outside specialists. The system had a rule fo...

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 being exposed to online at shockingly young ages — and how silence, shame, and lack of conversation can impact kids long-term.

Insi...

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 kids. She pulled them out, ditched the rigid curriculum, and built something that actually works for her spicy, high-energy family.

In this ep...

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:

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 isn’t just learning at home…
 He’s writing and publishing books, learning stock trading, and building real-world skills most adults were never...

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 constantly, and fits homeschooling right into the middle of all of it.

Cheryl and Jen get into the real stuff: the mom guilt, the...

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 and schedules. Ashley opens up about:

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 math when they’re actually ready, and why self-directed learning may be far more effective than most parent...

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 actually designed to help children like hers thrive.

She shares how her family transitioned from the UK school system to homeschooling, how environment and freedom dramatically changed her children’s confidence...

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’t working
 • Discovering her daughter’s dyslexia
 • Practical tools that helped
 • Why being “behind” isn’t failure
 • Creating a morning rhythm that works
 • How real-life learning beats rigid schedules

If you’ve ever wondered whether you’...

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: the erosion of childhood, creativity, and parental authority in modern education.

We talk about:

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 lecture hall.

Todd shares how their family found a hybrid homeschool rhythm, why “a good education” often just means “what we’ve always k...

Cheryl sits down with Katie Vieira — a former 4th grade teacher turned homeschool mom — to talk about what surprised her most when she stepped outside the traditional school system. They unpack how early academic pressure has changed, why many kids feel burnout younger than ever, and how standardized testing and school accountability can shape what happens in the classroom (and the stress teachers carry).

They also dive into the real-life side of homeschooling: finding community, handling seasons where screens sneak in more than you planned, keeping reading and learning positive when kids resist “lesson...

What does homeschooling look like after the kids are grown — and what advice actually holds up over 25 years? This week, I bring back a favorite episode of mine to help remind me what's really important while taking this homeschooling journey. 

In this episode of The Homeschool How To Podcast, I talk with Rosemary, a New Jersey mom of four who homeschooled all the way through high school and is now on the other side: kids launched, college decisions made, careers started, and the long view finally clear.

Rosemary shares the...

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 chose to homeschool their youngest child after experiencing both public school and homeschooling.

We also get practical...

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.

Janae shares what deschooling actually looks like (and why it’s harder for parents than kids), how she stopped trying to replicate school at home, and what h...

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 need to deschool themselves first. Courtney shares what she’s seen from inside education and why forcing kids...