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 homeschool
• What homeschooling looks like in Florida vs. New York (spoiler: way less paperwork)
• How Jen buys real estate without bank loans — and what that actually means
• Unit studies, Teaching Textbooks, and letting learning stay fluid
• Why your kids calling restaurants and understanding credit matters more than memorizing formulas
• How 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

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

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 Guide

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast

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 Substack
• Cheryl’s eBook- The Homeschool How To: Complete Starter Guide

If 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

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

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’re doing enough…
If your child struggles with reading…
If you’re juggling work and homeschooling…

This conversation will remind you that you have time — and that love of learning matters more than checklists.

Find Stephany:

IG @ivianaandco; @stephriosblog

www.stephriosblog.com (Blog)

www.ivianaandco.com (Jewelry)

Home(school) with Steph Podcast

📌 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

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:

• Why removing recess impacts behavior, mental health, and learning
• The rise of standardized testing (and what it’s costing kids)
• How education funding and influence shape curriculum decisions
• Why school choice and homeschooling are growing fast after COVID
• What Spencer discovered when he went undercover at an NEA leadership summit
• How parents can reclaim their role without fear

If you’re homeschooling, considering homeschooling, or trying to get your spouse on board, this episode will challenge your assumptions—and give you language for the conversations that matter.

🎥 Watch The Death of Recess on Angel Studios - click here!

📌 New here? Grab my free 30-day homeschool quick-start guide

Night Zookeeper is a gamified online language arts program with a parent dashboard for assigning work and tracking progress. Click here to check it out 🎮📚
👉 Click here for a free 7-day trial and 50% off your yearly subscription.

📘 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

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 known,” and how he made the leap from software sales to entrepreneurship so his work could align with his family’s mission.

You’ll also hear about the new text-message-based program Todd is launching—designed to help parents teach skills like emotional regulation, gratitude, growth mindset, and resilience in tiny daily moments (without adding more to your plate).

In this episode, we cover:

• Why “good schooling” isn’t always the same as a meaningful education
• Hybrid homeschooling: how it works and why it fits some families best
• Values over convenience (and why that changes everything)
• Teaching emotional skills before the meltdown happens
• Simple gratitude practices that actually rewire perspective
• From corporate ladder to calling: building a life with autonomy
• What Todd wants his kids to know by age 18 (hint: it’s not just academics)

Resources & Links

• Be Whole Do Good: bewholedogood.com (spelled: be whole do good)
• Night Zookeeper (free trial + 50% off yearly subscription)
• Cheryl’s eBook- The Homeschool How To: Complete Starter Guide- a compilation of everything she's learned from interviewing 150+ homeschool families
• Cheryl’s FREE 30-Day Homeschool Quick Start Guide: thehomeschoolhowto.com

If this episode encouraged you, follow the show and leave a review—it’s the best way to support the podcast.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast