The Homeschool How To

Cheryl - Host

I don't claim to know anything about homeschooling, so I set out on a journey to ask the people who do! Join me as I chat with homeschoolers to discuss; "why are people homeschooling," "what are all the ways people are using to homeschool today," and ultimately, "should I homeschool my kids?"

  1. #171: Homeschool Mom of 5 Gets Real About the Chaos — Multiple Ages, One Income, and Starting a Business

    3D AGO

    #171: Homeschool Mom of 5 Gets Real About the Chaos — Multiple Ages, One Income, and Starting a Business

    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 really like managing school with multiple ages under one roof (spoiler: it's not always pretty) → How Florida's PEP Scholarship is a total game-changer for families homeschooling on one income → The year-round model that actually relieved her stress → How she built Giplings — her small business inspired entirely by her homeschool journey → The car conversations, the lizard hunts, and the little moments that are the real education Whether you're just starting out or years in, Amanda's honesty about the chaos — and why she wouldn't trade it — will leave you feeling seen. Find Amanda + Giplings: Website: https://giplings.com/  Instagram: https://www.instagram.com/giplings/ Facebook: https://www.facebook.com/giplings YouTube: https://youtube.com/@giplings Wholesale: giplings.faire.com Resources from Cheryl: 🎓  New to homeschooling? Grab the free 30-Day Quick Start Guide   📚 Figure out exactly what to teach and how — What Do I Actually Teach? ($17)  💻 Homeschooling AND working? Check out the How to Work and Homeschool course  Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    49 min
  2. #170: They Shut Down Her Classroom Because Kids Were Getting Too Much Help

    MAY 16

    #170: They Shut Down Her Classroom Because Kids Were Getting Too Much Help

    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 for that too. We also get into the airway health connection to ADHD and behavior that nobody in a school can mention, how COVID masking quietly set back an entire generation of language development, and how Elyse now helps families with kids who have additional needs homeschool successfully — without doing it alone. In this episode: — Why your child's school limits services even when kids need more — The data vs. children problem hiding inside every IEP meeting — Airway health, sleep, and the hidden root causes of ADHD and behavior issues — How COVID masking impacted language development — Using AI to build a custom curriculum for any learning style — How to homeschool a child with additional needs Links: → Free 30-Day Homeschool Quick Start Guide → What Do I Actually Teach? ($17): thehomeschoolhowto.com/what-do-i-actually-teach CONNECT WITH ELYSE 🌐 Website:  speakinglife.co 🎙️ Podcast:  Speaking Life Into Motherhood 📱 Instagram:  @Speaking_life_into_motherhood 👥 Group Coaching Program: speakinglife.co/homeschoolplan 👉 Wisconsin Homeschool Expo: speakinglife.co/homeschool 📧 Email:  hello@speakinglife.co 🎁 Free Resource:  speakinglife.co/advocacy Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    44 min
  3. #169: Homeschooled, Sheltered & Addicted Young: A Conversation Every Parent Needs to Hear

    MAY 9

    #169: Homeschooled, Sheltered & Addicted Young: A Conversation Every Parent Needs to Hear

    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. Inside this episode: • what Logan wishes his parents had done differently • how over-sheltering can backfire • pornography addiction and dopamine-driven behavior • why vulnerable conversations matter more than perfect parenting • how to talk to kids without creating shame • the reality of parenting in the internet era • resources parents can use to start age-appropriate conversations This is a sensitive but incredibly important discussion for both homeschooling and non-homeschooling families alike. Listener discretion advised for younger ears. Resources: Good Pictures Bad Pictures https://www.conquerseries.com- For a man who might be struggling or a woman who is close to a man who struggles, the best single resource to gain an education of how sexual addiction works is the Conquer Series Follow Logan on Instagram 🎯 Ready to learn how families are actually working + homeschooling?  Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out!👉 How to Work & Homeschool (Without Burning Out) Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    38 min
  4. #168: Homeschooling Through Grief: A Former Teacher's Raw and Honest Story

    MAY 2

    #168: Homeschooling Through Grief: A Former Teacher's Raw and Honest Story

    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 episode: Why connection over perfection changed everything for her familyHow she homeschools four kids aged 5–12 using interest-led unit studiesWhat homeschooling through the loss of her mother actually looked likeSouth Carolina's homeschool options and fundingWhy socialization was never actually a problemBarbara also shares her memoir and upcoming Bible study guide for homeschooling through grief — because sometimes life takes the rug out from under you, and you still have to be there for your family. Connect with Barbara here:  https://a.co/d/0bMqCMiq Barbara's Instagram 🎯 Ready to learn how families are actually working + homeschooling? Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out!👉 How to Work & Homeschool (Without Burning Out) Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    31 min
  5. #167: When the School Said 'Behind' — One Mom Said 'Watch Me'

    APR 25

    #167: When the School Said 'Behind' — One Mom Said 'Watch Me'

    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 bought them timeWhy Katherine walked away from a 14-year Foreign Service careerThe year they moved to Florida, ditched the diagnosis, and just learned to liveHow her son went from nonverbal to reading Green Eggs and Ham — on his own timelineBuilding a homeschool pod in Kenya with kids of all agesHer AI code of ethics for kids (yes, they have written rules)What "symphonic thinking" is and why it's the most future-proof skill you can teachWhether you're just starting out or deep in the homeschool journey, Katherine's story will remind you: you know your kid best. Trust that. Connect with Katharyn:  Substack: https://substack.com/@kairoslearninglifestyle?utm_campaign=profile&utm_medium=profile-page Instagram: https://www.instagram.com/radicallyresetting/?hl=en YouTube: https://www.youtube.com/@KairosRiseHomeschool www.KairosRise.com 🎯 Ready to learn how families are actually working + homeschooling? Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out!👉 How to Work & Homeschool (Even as a Single Parent!) Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    43 min
  6. #166: How Homeschooling Her Only Child Turned Him Into a 9-Year-Old Author & Stock Trader

    APR 18

    #166: How Homeschooling Her Only Child Turned Him Into a 9-Year-Old Author & Stock Trader

    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 taught. We also get into:  What homeschooling an only child actually looks like (social life + community)  How Classical Conversations works in real life  Why creativity and imagination often get shut down in traditional school  How they approach raising a child without a fixed path The mindset shift that allows families to “level up” without pressure And if you’ve ever wondered how families actually make working + homeschooling work… I break down the patterns I’ve seen from interviewing 200+ families and how you can apply them. If you’re thinking about homeschooling—but feel stuck on the how—this episode will open your mind to what’s possible. Find Laresia & Family: https://kidpreneurconnection.com/ - https://www.youtube.com/@areeson2love - https://corelife365.com/ 🎯 Ready to learn how families are actually working + homeschooling? Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out below! 👉 How to Work & Homeschool (Even as a Single Parent!) Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    33 min
  7. #165: She Left Teaching, Bought Houses Without a Bank, and Homeschools 2 Kids

    APR 11

    #165: She Left Teaching, Bought Houses Without a Bank, and Homeschools 2 Kids

    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 chaotic seasons, the creative finance deals, and why letting your 13-year-old message sellers counts as school. This one's for the homeschool moms who are also building something — and the ones wondering if they even can. In this episode: How COVID pushed Jen from virtual school to full homeschoolWhat homeschooling looks like in Florida vs. New York (spoiler: way less paperwork)How Jen buys real estate without bank loans — and what that actually meansUnit studies, Teaching Textbooks, and letting learning stay fluidWhy your kids calling restaurants and understanding credit matters more than memorizing formulasHow to work, invest, and homeschool without burning out"Hustle should be a season, not a lifestyle." Find Jen: Instagram: @jenDelleFave Website: CreativeFinancePlaybook.com 🎯 Ready to learn how families are actually working + homeschooling? Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out below! 👉 How to Work & Homeschool (Even as a Single Parent!) Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    46 min
  8. #164: Teachers Are Leaving the System—Here’s Why (Homeschool + Work Reality)

    APR 4

    #164: Teachers Are Leaving the System—Here’s Why (Homeschool + Work Reality)

    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:  What teachers see inside schools that most parents don’t  Why more educators are choosing to homeschool their own kids  How to balance working from home while homeschooling  The truth about socialization, co-ops, and hybrid homeschool models  Why homeschooling gives families more freedom, flexibility, and connection  Letting go of “balance” and embracing seasons of life If you’ve ever thought:  “Can I homeschool if I still need to work?”  or  “I feel called to homeschool but don’t know how to make it work…” This episode will give you clarity, encouragement, and a real-life look at what’s possible. 🎯 Ready to learn how families are actually doing this? Cheryl has interviewed 200+ homeschool families—and put a step by step process together for how to work and homeschool (even as a single parent!) Check it out below! 👉 How to Work & Homeschool (Even as a Single Parent!) Find Ashley at: https://linktr.ee/mrsashleymartinez Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    55 min
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4.8
out of 5
100 Ratings

About

I don't claim to know anything about homeschooling, so I set out on a journey to ask the people who do! Join me as I chat with homeschoolers to discuss; "why are people homeschooling," "what are all the ways people are using to homeschool today," and ultimately, "should I homeschool my kids?"

Information

  • Creator
    Cheryl - Host
  • Years Active
    2023 - 2026
  • Episodes
    180
  • Rating
    Clean
  • Copyright
    © 2026 The Homeschool How To
  • Show Website
    The Homeschool How To

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