The Smiling Homeschooler Podcast

Latest Episodes:

Episode 385 - You Don’t Have to Do It All: Letting Go of Homeschooling Pressure Dec 31, 2025

Show notes

Welcome to The Smiling Homeschooler Podcast! This week we’re taking a short break to celebrate the New Year. But don’t worry—we’ve got a fantastic episode from our archives for you!

Today we’re talking about the pressure so many homeschooling moms feel to teach it all… to hit every subject… and to start earlier and earlier with their kids. Our hope is to take some of that pressure off and remind you that it’s okay to let a few things slide.

Before we get started, we want to thank Teaching Textbooks for making The Smiling Homeschooler possible. They’re an amazing math curriculum, and we encourage you to check them out at teachingtextbooks.com.

We’d also like to thank Samaritan Ministries—a community of Christians who help one another with medical bills. They make it possible for families to take steps of faith, whether that’s a career change, ministry opportunity, or bringing mom home. You can learn more and support us through this link https://hubs.ly/Q03VZKNS0.

Episode 384 - The Moments Our Kids Will Remember Dec 24, 2025

Show notes

Welcome back to The Smiling Homeschooler. We’re really glad you’re here with us today!

We’re talking about memories. Not just big moments or picture-perfect days, but the kinds of memories our kids will carry with them when they’re grown—the feeling of being safe, known, and loved; the traditions we repeat year after year; and the time we choose to simply be together. We also want to talk honestly about how our minds often let the hard parts fade, while connection and relationship seem to last.
If you’ve ever worried that you’re not doing enough, or that the difficult seasons might overshadow everything else, this conversation is meant to be encouraging. Because choosing relationship, presence, and togetherness—especially in the ordinary moments—has a way of paying off in the long run.

We want to thank Teaching Textbooks for making the Smiling Homeschooler possible. They are an amazing math curriculum, and we would encourage you to check them out over at teachingtextbooks.com

Lastly, Thank you to Samaritan Ministries, a community of Christians that pay one another’s medical bills…helping families take a safe step of faith as they feel God’s Leading in career or ministry changes or in bringing mom home. You can learn more and support us by clicking the link https://hubs.ly/Q03VZKNS0

Have a great week and don't forget to smile!

Episode 383 - When Friendship Is Hard (For Moms and Kids) Dec 17, 2025

Show notes

Hey everybody, welcome back to The Smiling Homeschooler podcast. Today we’re spending some time talking about friendships—for moms and for kids. This conversation was prompted by a message we got from a mom whose son is really struggling to find meaningful connection, even though they’re involved in church, homeschooling, and community. So we want to talk honestly about why friendships can be harder than we expect, the fears that drive us as parents, and what we can—and can’t—control when it comes to helping us and our kids build real relationships.

We want to thank Teaching Textbooks for making the Smiling Homeschooler possible. They are an amazing math curriculum and we would encourage you to check them out over at teachingtextbooks.com

Lastly, thank you to Samaritan Ministries, a community of Christians that pay one another’s
medical bills…helping families take a safe step of faith as they feel God’s Leading in career or ministry changes or in bringing mom home. You can learn more and support us by clicking this link https://hubs.ly/Q03VZKNS0

Have a great week and don't forget to smile!

Episode 382 - Simple Ways to Encourage a Mom This Christmas Dec 10, 2025

Show notes

Hey everybody, welcome back to The Smiling Homeschooler podcast. Christmas is coming fast, and today we’re spending some time talking about something super practical—what to actually get your husband for Christmas. Not the gimmicky stuff, but the quality gifts dads really appreciate, the things that last and feel meaningful.

We’re also talking about gifts you can give other homeschooling moms, and not the things you buy from a store. Christmas can be overwhelming for a lot of homeschool moms, so we’re sharing some simple, thoughtful ways you can encourage another mom right now. Nothing big or perfect—just real reminders that she’s doing a good job and she’s not alone.

We want to thank Teaching Textbooks for making the smiling homeschooler possible. They are an amazing math curriculum and we would encourage you to check them out over at teachingtextbooks.com

Thank you to Samaritan Ministries, a community of Christians that pay one another’s medical bills…helping families take a safe step of faith as they feel God’s Leading in career or ministry changes or in bringing mom home. You can learn more and support us by clicking the link

https://hubs.ly/Q03VZKNS0

Episode 381 - Breaking Free From the Lies of Fear Dec 03, 2025

Show notes

Welcome to the Smiling Homeschooler Podcast. This week we’re focusing on something every homeschooling mom faces but isn’t always willing to talk about: fear. The fear of not measuring up, the fear of failing our kids, the fear that we aren’t enough for our children, and so many more. We walk through the most common fears parents carry, how those fears shape our decisions, and how to replace the lies with the truth, hope, and confidence that God provides. It’s a great conversation, and we hope you enjoy it!

We want to thank teaching textbooks for making the smiling homeschooler possible. They are an amazing math curriclulm and we would encourage you to check them out over at teachingtextbooks.com

Also, thank you to Samaritan Ministries, a community of Christians that pay one another’s medical bills…helping families take a safe step of faith as they feel God’s Leading in career or ministry changes or in bringing mom home. You can learn more and support us by clicking this link https://hubs.ly/Q03VZKNS0

Have a great week and don't forget to smile!

Episode 380 - Guarding Their Hearts: What Should Our Kids Watch? - With Sam Wilson Nov 26, 2025

Show notes

Welcome to the Smiling Homeschooler Podcast! This week, we’re diving into a topic every homeschooling family wrestles with: deciding what content, movies, and shows we allow into our homes. We talk through how we make those decisions, what standards guide us, and share a few recommendations that have worked well for our families.

We are also joined by a very special guest — Todd's son, Sam Wilson, lead animator for Season 3 of The Wingfeather Saga. He gives us an inside look at the new season and why this series stands out as a great option for families.
It’s an encouraging and practical conversation about media, discernment, and enjoying thanksgiving together as a family

We also want to thank teaching textbooks for making the smiling homeschooler possible. They are an amazing math curriculum and we would encourage you to check them out over at teachingtextbooks.com

Lastly, we want to thank Samaritan Ministries, a community of Christians that pay one another’s
medical bills…helping families take a safe step of faith as they feel God’s
Leading in career or ministry changes or in bringing mom home. You can learn more at https://hubs.ly/Q03CR00H0

Have a great week and don't forget to smile!

Episode 379 - The Lessons That Stick Aren't From a Textbook Nov 19, 2025

Show notes

Hey everyone, welcome to The Smiling Homeschooler Podcast. Todd flies solo this week and he shares an honest look at homeschool basketball season — the joys, the exhaustion, and the commitment to showing up for our kids. He encourages parents not to feel guilty about what they aren’t doing, but to celebrate the memories they are making.

Todd then dives into the idea of “electives” in homeschooling — and why in a homeschool environment, everything can be an elective! From animation to hair styling to basketball, the things your children love can be just as valuable (or more valuable) than the so-called “core” subjects.

As the holidays approach, remember that enjoying the season is school. Holiday crafts, traditions, decorating, and serving together are the real-life lessons your children will carry into adulthood.

We want to thank Teaching Textbooks for making The Smiling Homeschooler possible. Their match curriculum helps thousands of homeschoolers smile each and every day, and we would encourage you to check it out for next school year over at teachingtextbooks.com.

Also, today’s show is being underwritten by Samaritan Ministries, a community of Christians who pay one another’s medical bills, helping families take a safe step of faith as they feel God’s leading in career or ministry changes, or in bringing moms home. You can learn more at SamaritanMinistries.org/familyman

Episode 378 - Homeschooling During a Hard Season of Life - With Rissa Wilson Nov 12, 2025

Show notes

Welcome to The Smiling Homeschooler Podcast. We are really glad you’re here today, because this week’s episode is going to be a little different. Ben's wife, Rissa, is joining him, and she’s opening up about some of the struggles she’s been walking through over the past few months. She’s going to share honestly about what homeschooling can look like when life feels heavy, and offer encouragement to any mom who’s in a tough season right now.

So if you’ve been feeling worn out or like you’re not doing enough — you’re not alone. This episode is full of grace and hope, and we think it’s going to really encourage you.

Have a great week and don't forget to smile!

Episode 377 - Making Math Less Miserable Nov 05, 2025

Show notes

Welcome back to The Smiling Homeschooler Podcast!
We’re glad you’re here. This week, we’re talking all about math—what really matters, how we actually use it in everyday life, and how you can help your kids (and maybe yourself) smile a little more while doing it.

Have a great week and don't forget to smile!

Episode 376 - Investing in Family: Why Vacations and Breaks Matter Oct 29, 2025

Show notes

Welcome back to The Smiling Homeschooler Podcast!
This week on The Smiling Homeschooler Podcast, we’re back from vacation and talking about why family trips are worth every penny.
Vacations can be expensive and a lot of work — especially with kids — but we believe they’re an incredible investment in your family’s relationships and memories. We also chat a bit about taking breaks during the homeschooling year and share a few thoughts about Halloween.

Have a great week and don't forget to smile!

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