The Homeschool How To

Cheryl - Host
  • 4.8 (99)
  • EDUCATION
  • UPDATED WEEKLY

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

    4D AGO

    #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
  2. #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
  3. #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
  4. #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
  5. #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
  6. #163: The More Self-Sufficient You Are, the Less You Need School

    MAR 28

    #163: The More Self-Sufficient You Are, the Less You Need School

    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:  Why play-based learning may be more powerful than structured classrooms  How environment (indoor vs outdoor living) impacts children’s development  The connection between food, health, and independence  Simple ways families can become more self-sufficient (even if you’re busy)  What it looks like to raise kids outside the traditional system While this conversation isn’t just about homeschooling, it touches on a core idea many parents are starting to realize: We have more control over our children’s lives—and learning—than we’ve been led to believe. If you’ve ever questioned the way things are “supposed” to be done, this episode will give you a lot to think about. Episode Resources: The Sprouting Company Instagram- The Sprouting Company https://www.youtube.com/@TheSproutingCompany Cheryl’s eBook- The Homeschool How To: Complete Starter GuideSupport the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    41 min
  7. #162 Dr. Peter Gray: What Schools Get Wrong About Learning

    MAR 21

    #162 Dr. Peter Gray: What Schools Get Wrong About Learning

    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 parents have been led to believe. If you’ve ever wondered whether your child is really “behind,” whether school is preparing kids for life, or whether there’s a better way to learn, this conversation will challenge the way you think about education. In this episode, we discuss:  what schools were originally designed to do  why forced learning often backfires  reading without a rigid timeline  math anxiety and real-life math  why motivation changes everything  how children learn when they’re trusted About Dr. Peter Gray: Dr. Peter Gray is a research professor, psychologist, and author of Free to Learn. His work focuses on self-directed education, play, and the ways modern schooling conflicts with children’s natural development. Resources mentioned: Free to Learn by Dr. Peter Gray Dr. Gray's website: https://www.petergray.org/Check out Dr. Gray's SubstackCheryl’s eBook- The Homeschool How To: Complete Starter GuideIf this episode encouraged you, be sure to follow the show, leave a review, and share it with a parent who needs to hear this. Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    59 min
  8. #161: When School Failed Her Neurodivergent Kids, She Built a Worldschooling Life in Spain

    MAR 14

    #161: When School Failed Her Neurodivergent Kids, She Built a Worldschooling Life in Spain

    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, and why self-directed learning can be especially powerful for neurodivergent kids. Cheryl and Corey also discuss worldschooling, socialization outside the classroom, learning to read when children are truly ready, and why giving kids agency over their time can unlock creativity and real-life skills. Today Corey runs a worldschooling community in Spain where homeschooling families gather to learn, explore, and grow together. If you’re a homeschooling parent—or considering home education for a neurodivergent child—this conversation will open your mind to what’s possible. Find Corey here: www.shepherdsrest.org   Facebook: www.facebook.com/shepsrest  Instagram: www.instagram.com/shepsrest  📌 New here? Grab my free 30-day homeschool quick-start guide  🎹 Looking for a fun, simple way to introduce piano at home? We’ve loved using Simply Piano. It turns lessons into interactive challenges so kids can start playing real songs right away — without pressure or frustration. 👉 Click here to check it out! 📘 Feeling overwhelmed about where to start with homeschooling? After three years of interviewing homeschooling families, I compiled the best advice, practical tips, key questions, and trusted resources into one clear, actionable e-book: The Homeschool How To Complete Starter Guide. 👉 Grab it here! Support the show Instagram: TheHomeschoolHowToPodcast Facebook: The Homeschool How To Podcast

    44 min
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4.8
out of 5
99 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
    177
  • Rating
    Clean
  • Copyright
    © 2026 The Homeschool How To
  • Show Website
    The Homeschool How To

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