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 approach that shaped her homeschool—part structure, part freedom—with a few non-negotiables (like math facts and early reading), plus a powerful reminder: you’re replaceable at work… but irreplaceable in your child’s life.

You’ll also hear:

• Why agency is one of the biggest gifts homeschooling can give
• How she balanced academics + interests + sports as kids got older
• When and why she started testing (and what she learned)
• How her kids handled the culture shock of college environments
• A practical framework every family can use: Dojo • Cafeteria • Library
• A “well-kept secret” resource: Learning Unlimited (Saturday classes taught by graduate students)

If you’re new to homeschooling—or you’re deep in the weeds—this conversation will help you zoom out and build a homeschool that’s less about checklists and more about raising capable, grounded kids who know how to learn.

 🎹  Have your kiddos learn piano from this amazing resource, check out: Simply Piano. We love it!  🎶 

Cheryl's ebook: The Homeschool How To: Complete Starter Guide

🎁 Free resource: Grab my free 30-day homeschool quick start guide at thehomeschoolhowto.com

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

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: Kiri explains a simple framework that helps parents homeschool with confidence—separating “learning” (reading, writing, math) from “learning about” (curiosity-led unit studies). She shares her favorite strategy (the “curiosity jar”) to turn your child’s questions into meaningful learning without recreating school at home.

Finally, Kiri talks about her work as the founder of Chicken Scratch Books, a publisher creating clean, traditional middle grade fiction for families who want books they can trust.

In this episode, we cover:

• Why Kiri left teaching and what she noticed shifting in schools
• Common Core, testing pressure, and how it affects classrooms
• Why homeschooling can take less time and lead to deeper learning
• The “curiosity jar” method for interest-led homeschooling
• Building lifelong learners and confident, capable kids
• Chicken Scratch Books and choosing better middle grade reads

Guest: Kiri Jorgensen
Website: chickenscratchbooks.com

Follow the show, leave a review, and share this episode with a parent who needs reassurance today.

Mentioned in today’s episode:

 🎹  Have your kiddos learn piano from this amazing resource, check out: Simply Piano. We love it!  🎶 

Cheryl's ebook: The Homeschool How To: Complete Starter Guide

🎁 Free resource: Grab my free 30-day homeschool quick start guide at thehomeschoolhowto.com

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

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 happened when her children finally had room for boredom, curiosity, and real learning: guitar skills built through YouTube lessons, reading for meaning (not grades), embroidery that turned into paid work, early jobs, business books, conferences, and a senior year centered on debate, confidence, and entrepreneurship.

If you’re thinking, “I’m not smart enough,” “My kids will fight me,” or “Is it too late to start homeschooling — especially for middle and high school?” this conversation will give you clarity, encouragement, and a new definition of education.

Connect with Janae:
Instagram
Facebook
YouTube
Website

Follow the show, leave a review, and share this episode with a parent who needs reassurance today.

Mentioned in today’s episode:

 🎹  Have your kiddos learn piano from this amazing resource, check out: Simply Piano. We love it!  🎶 

• Cheryl's ebook: https://thehomeschoolhowto.com/ebook
  
  

🎁 Free resource: Grab my free 30-day homeschool quick start guide at thehomeschoolhowto.com

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

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 to meet grade-level standards can backfire — especially when kids develop at different rates.

We also get into:

• What unschooling really means (and why it’s not “kids watching TV all day”)
• Why school “socialization” can be toxic and what healthy socialization looks like
• How to handle screen time without power struggles (and why curiosity matters)
• The link between anxiety, nervous system regulation, and learning
• Why many kids are labeled too early — and what parents can do instead
• How to spark learning naturally through real life, nature, conversation, and connection
• A fascinating look at Human Design as a tool for understanding how your child learns

If you’re a parent who’s trying to homeschool without recreating school at home — and you want your child to grow in confidence, curiosity, and love of learning — this episode will help you breathe again.

 📌 Links to Courtney’s work: https://linktr.ee/courtney_shakti

Follow the show, leave a review, and share this episode with a parent who needs reassurance today.

Mentioned in today’s episode:

• My ebook: https://thehomeschoolhowto.com/ebook
  
  
• My children’s safety book Let’s Talk, Emergencies!: grab it on Amazon!

🎁 Free resource: Grab my free 30-day homeschool quick start guide at thehomeschoolhowto.com

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

What happens when you stop accepting the “official story” and start asking better questions—about education, parenting, freedom, and the systems we’ve all been told to trust?

In this week’s episode of The Homeschool How To Podcast, I’m joined by Tim (ANCAPTim)—a homeschooling dad, songwriter, and outspoken advocate of voluntary exchange, individual responsibility, and a truly free market. We talk about what anarcho-capitalism means in plain language, how his worldview shaped his decision to homeschool, and how to raise curious, grounded kids without turning them into “the weird kid on the playground.”

We also get into:

• Why “both sides” can feel like two wings of the same bird
• Homeschooling as a custom fit for individual kids (not a one-size box)
• Unschooling explained without the stereotypes
• Consumer responsibility, ethics, and “voting with your wallet”
• AI, creativity, and what tech might change (and what it won’t)

Connect with Tim + his music:
 ANCAPTIM.com 

Mentioned in today’s episode:

• My ebook: https://thehomeschoolhowto.com/ebook
  
  
• My children’s safety book Let’s Talk, Emergencies!: https://CherylDaley.com or grab it on Amazon!
  
  

If you enjoyed this conversation, please follow the show and leave a review—it helps more homeschool families find the podcast.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

What happens when a homeschooled kid grows up, skips the “missing out” narrative, and builds a real community of motivated teens who want to create, lead, and launch?

In this episode of The Homeschool How To Podcast, I’m joined by Malcolm—a homeschooled graduate who spent years in Classical Conversations (CC) and is now the founder of Teen Mastermind, a fast-growing entrepreneurship community for teens that’s already reaching beyond the U.S.

We talk about what homeschooling was actually like from the student perspective—socialization, friendships, motivation, prom/homecoming alternatives, and why Malcolm says he didn’t miss out… he dodged a bullet. You’ll also hear a clear, simple breakdown of the classical education model (grammar, dialectic/logic, rhetoric) and how CC works week-to-week for families considering it.

Then we go deeper into the part parents don’t always know how to teach: entrepreneurship. Malcolm shares what he learned from attending business events with his family, why masterminds matter, and how being around the right people can change a teen’s trajectory.

If you’ve ever wondered:

• “Will my kids resent homeschooling?”
• “How do homeschoolers actually make friends?”
• “Is Classical Conversations worth it?”
• “How do I raise a motivated teen with real-world skills?”

…this episode is for you.

Resources mentioned:

• theteenmastermind.com
• teenmastermindlive.com

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

You know your child better than any teacher, curriculum, or system ever could — but trusting that instinct can feel scary.

In this episode of The Homeschool How To Podcast, I’m joined by Leanne, a former classroom teacher, homeschool mom of two grown kids, and Unfold History co-creator, to talk honestly about what homeschooling really looks like over the long haul.

We dive into:

• How to know when a curriculum isn’t working — and when to switch
• Why learning should be engaging, exciting, and sometimes messy
• The freedom homeschooling gives families beyond academics
• The impact of screens, dopamine, and constant stimulation on developing brains
• Why college doesn’t have to be the end goal — and what success can actually look like
• How homeschooling can strengthen family bonds well into adulthood

🎬 Unfold History

Leanne is also one of the creators behind Unfold History, a live-action, story-based history program for kids designed to make history meaningful, visual, and relatable. The program uses short, kid-centered videos paired with flexible curriculum to help children understand why history matters — not just memorize facts.

Whether you’re homeschooling, exploring alternative education, or simply questioning the traditional school system, this episode will remind you that there is no single “right” path — only the one that works for your family.

🎧 Listen in and be encouraged: you can do this.

Check out: www.unfoldhistory.org

Follow Unfold History on Instagram and Facebook

The documentary mentioned is actually called : The Social Dilemma (not The Social Experiment!) 

📘 The Homeschool How To Complete Starter Guide
Thinking about homeschooling but don’t know where to start? Cheryl created this comprehensive guide, compiling insights from interviews with over 120 homeschooling families across the country. From navigating state laws to balancing work and home life — this eBook covers it all. Stop feeling overwhelmed and start feeling confident on your homeschooling journey.

👉 15% off Tuttle Twins books with code Cheryl15

Let's Talk, Emergencies!- Grab it on Amazon!
What is the most important thing we can teach our kids?
HOW TO HANDLE AN EMERGENCY!

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

What if one of the biggest homeschooling wins isn’t curriculum… but protecting your kids from modern pressures and modern “food”?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Patrick & Ashley—homeschool-connected entrepreneurs and the team behind Jigsaw Health—to talk about:

• Patrick’s experience being homeschooled in 7th–9th grade (and why it mattered)
• The myth of “socialization” vs. what homeschool kids actually gain
• Why food choices have become a parenting issue (and a homeschooling advantage)
• Their documentary Breaking Big Food: How the American Food System Went Rotten and How It’s Being Revived
• Practical, realistic “one step at a time” swaps (without turning your life upside down)
• Why “pay the farmer now or pharma later” keeps showing up in this conversation

You’ll also hear how families are building local alternatives—farmers markets, seed-oil-free restaurants, community markets—and how you can start making changes without getting overwhelmed.

🎥 Watch the documentary: BreakingBigFood.com 

Ashley & Patrick's supplement brand: JigsawHealth.com and their organic coffee shop: FireflyScottsdale.com

If you’re homeschooling (or considering it) and you care about kids’ health, behavior, focus, food dyes, ultra-processed foods, and raising well-adjusted humans, this episode will give you both encouragement and next steps.

Follow/subscribe for weekly interviews with homeschooling families and experts—and share this episode with a friend who’s trying to “do better” but doesn’t know where to start.

Learn more about Green Ember: Helmer in the Dragon Tomb—the new prequel book from S. D. Smith—and explore the companion video game now available on Steam: sdsmith.com/helmer 

Perfect for parents seeking meaningful, courage-building stories for kids ages 8–12.

📘 The Homeschool How To Complete Starter Guide
Thinking about homeschooling but don’t know where to start? Cheryl created this comprehensive guide, compiling insights from interviews with over 120 homeschooling families across the country. From navigating state laws to balancing work and home life — this eBook covers it all. Stop feeling overwhelmed and start feeling confident on your homeschooling journey.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

Homeschooling isn’t just about math lessons and reading charts—it’s about who gets to shape how your kids see the world.

In this episode, I’m joined by Dr. Jonathan Newman from the Mises Institute, a homeschooling dad, economist, and libertarian who breaks down why he and his wife chose to keep their kids out of government schools, how they approach reading and “adulting” skills at home, and why there’s really no such thing as a “neutral” education.

We talk about:

• Teaching kids to read with Teach Your Child to Read in 100 Easy Lessons—and why it works for some kids and not others
• The big differences between boys and girls when it comes to focus, readiness, and timelines
• Why homeschooling is so much more efficient than public school (and what to do with all that extra time together)
• The “adulting crisis” and how kids actually learn real-life skills like changing a tire, paying bills, and mailing a letter
• What Austrian economics is, why the Mises Institute exists, and how Jonathan teaches multiple perspectives instead of one government-approved narrative
• Capitalism vs. socialism, and why socialist systems struggle to get food, prices, and production right
• Indoctrination, values, and why parents—not the state—should decide which ideas get center stage in their child’s education

If you’re a Christian, liberty-minded, or simply skeptical of the one-size-fits-all system and the stories your kids are being told about history, money, and government, this conversation will give you a lot to think about.

Follow Dr. Jonathan Newman on X - @NewmanJ_R

Discover free books, articles, and lectures on economics and liberty at Mises.org

Learn more about Green Ember: Helmer in the Dragon Tomb—the new prequel book from S. D. Smith—and explore the companion video game now available on Steam: sdsmith.com/helmer 

Perfect for parents seeking meaningful, courage-building stories for kids ages 8–12.

📘 The Homeschool How To Complete Starter Guide
Thinking about homeschooling but don’t know where to start? Cheryl created this comprehensive guide, compiling insights from interviews with over 120 homeschooling families across the country. From navigating state laws to balancing work and home life — this eBook covers it all. Stop feeling overwhelmed and start feeling confident on your homeschooling journey.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

What happens when vaccine mandates, school regulations, and a mama’s intuition collide? In this episode, I sit down with Tiffany, a homeschool mom of almost-seven-year-old twin boys in West Virginia and an occupational therapist who now serves the homeschool community.

Tiffany shares how COVID, vaccine requirements, and a strong Christian conviction opened the door to homeschooling—not just for her twin boys, but for her stepkids too. We talk about co-ops, jujitsu, piano lessons, state requirements, and why “freedom” is the first word that comes to mind when she thinks of home education.

As an OT, Tiffany also dives into reflex integration—how primitive reflexes can affect things like handwriting, reading, attention, picky eating, emotional regulation, and why some kids “can’t sit still” no matter how hard they try. If you’ve ever wondered, “Is this just a phase, or does my child actually need help?” this conversation is for you.

In this episode, we cover:

• Homeschooling energetic twin boys with totally different strengths
• Navigating co-ops, church life, and daily rhythms in West Virginia
• How vaccine mandates and religious convictions pushed some families toward homeschooling
• The difference between classical education and programs like Classical Conversations
• West Virginia vs. New York homeschool requirements (portfolio reviews, testing, paperwork)
• What pediatric occupational therapy actually is for homeschoolers
• Reflex integration 101 and how unintegrated reflexes can show up as
  • Poor handwriting
  • Trouble sitting still
  • Visual scanning issues when reading
  • Picky eating, chewing on clothes/pencils
  • Big emotions and meltdowns
• Why it’s okay to ask for help and build your “village” as a homeschool parent

Connect with Tiffany:

Www.agapelove.com

Facebook: The Homeschool OT, Tiffany Parsons

Other therapy resources: 

Www.HomeschoolOT.com 

Facebook: The Homeschool OT, Sarah Collins

Harkla (parent trainings): https://harkla.co/?rfsn=8716597.365cfae

Learn more about Green Ember: Helmer in the Dragon Tomb—the new prequel book from S. D. Smith—and explore the companion video game now available on Steam: sdsmith.com/helmer 

Perfect for parents seeking meaningful, courage-building stories for kids ages 8–12.

📘 The Homeschool How To Complete Starter Guide
Thinking about homeschooling but don’t know where to start? Cheryl created this comprehensive guide, compiling insights from interviews with over 120 homeschooling families across the country. From navigating state laws to balancing work and home life — this eBook covers it all. Stop feeling overwhelmed and start feeling confident on your homeschooling journey.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast