Homeschooling Multiple Children at Different Stages | From Diapers to Division
Release Date: 01/06/2026
Everyday Educator
Does homeschooling have you ready to quit? You're not alone — and you're not failing. In this episode of the Everyday Educator podcast, host Lisa Bailey and 7-year Classical Conversations mom DeDe Adetutu get real about the winter doldrums, talk about why finishing strong actually matters, and share the practical strategies — and a little Yoruba wisdom — that have helped their families push through to the finish line. This one is equal parts encouragement and action plan. Lisa Bailey opens by naming what so many homeschool moms feel but rarely say out loud: February is hard. The holidays...
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You may already recognize his voice. For thousands of Classical Conversations families, Charles Hall — known simply as "Internet Grandpa" — has become one of the most beloved figures in the homeschool community, reading rich living books aloud on YouTube and blessing families he has never met. In this episode of the Everyday Educator, host Kelli Wiltsits down with Mr. Hall to talk about how it all started, what it means to hear a human voice read a story, and what happens when faithful work runs into unexpected obstacles. Charles Hall never set out to become Internet Grandpa. It started...
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What if the most important thing you teach your child has nothing to do with curriculum? In this episode of the Everyday Educator podcast, host Emma Bortins sits down with her mother-in-law and Classical Conversations founder Leigh Bortins to discuss the ideas behind her new book, The Habits: Practicing the Art of Grammar. Together they explore how naming, attending, memorizing, expressing, and storytelling build the foundational habits that help children — and homeschool families — truly flourish. If you're a homeschool mom looking for a classical Christian approach to raising lifelong...
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Is pushing for Memory Master worth it — and what happens if your child doesn't make it? In this episode of the Everyday Educator podcast, host Amy Jones sits down with veteran CC moms Courtney Bradshaw and Tunrade Schumann to talk about how to challenge your kids with Classical Conversations memory work without overwhelming them or pushing too hard. Whether you're aiming for Memory Master, Subject Master, or just want your child to engage more deeply with the Foundations curriculum, this conversation is full of warm, practical wisdom for every homeschool family. Tunrade shares how her family...
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Is progressive Christianity coming for your kids — and would you even recognize it if it was? In this episode of the Everyday Educator podcast, host Amy Jones and co-host Emma Bortins sit down with author and apologist Alisa Childers to unpack what progressive Christianity actually is, why it appeals to young people, and how Christian homeschool parents can equip their children to stand firm in biblical truth. If you're raising kids in today's cultural climate, this conversation is one you can't afford to miss. Alisa shares her own story of encountering progressive Christianity through a...
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In this episode of Everyday Educator, host Lisa Bailey is joined by Amy Jones and Ginny Tran to explore why memorizing matters — for your children and for you. From scripture memory to poetry and classical memory work, discover how memorization builds wisdom, shapes character, and hides beauty in your heart for life. Amy and Ginny share their earliest memories of memorizing — from singing the books of the Bible at church to reciting Twas the Night Before Christmas by the warmth of a mother's voice — and what those moments reveal about how our brains and hearts learn together. Lisa adds...
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What does it really mean to pass on virtue to your children—and how do you do it in the midst of everyday homeschool life? Join host Amy Jones and veteran homeschooler Chelly Barnard for a rich conversation about cultivating moral goodness in your home. Discover how Classical Conversations' Common Topics can help you define and teach virtue, why reading aloud to your kids well into high school matters more than you think, and practical ways to weave biblical truth into daily conversations without being "preachy." Chelly shares wisdom from 25 years of homeschooling experience, emphasizing...
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Wondering if your child is ready to start Foundations? Join Delise Germond and Lisa Bailey in this episode of Everyday Educator as they discuss practical signs of school readiness for preschoolers and early learners. Discover how to prepare your child for Classical Conversations Foundations, navigate emotional development milestones, and build essential skills like following directions, fine motor development, and independent play. Learn when to start formal learning, how to give constructive feedback as a homeschool parent, and why emotional intelligence matters as much as academic...
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What if learning Latin could actually be... fun? Join Lisa Bailey and Tobin Duby as they take you on a delightful journey through the world of Parent Practicum and Latin—two things that might sound intimidating but are actually gateways to lifelong learning for your entire family. Tobin shares hilarious behind-the-scenes stories from filming practicums across the country (including the tale of a toddler handing him her yogurt trash), while Lisa opens up about her own "hillbilly belt" moment that brought down the house. But beyond the laughter, discover why practicum is the perfect summer...
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Join Delise Germond as she sits down with Robert Bortins, CEO of Classical Conversations and homeschool dad of three, for an engaging conversation about family legacy, educational freedom, and his new book Woke and Weaponized. Robert shares his personal journey from being one of the first 11 students in Classical Conversations to leading the organization for over 13 years. He opens up about the family values that shaped him—hard work, self-discipline, and carrying the family name with honor—and how he's now passing these principles to his own children through practical strategies like job...
info_outlineFeeling overwhelmed by homeschooling kids at different stages? You're not alone—and we've got the encouragement (and practical tips) you need!
Join Delise Germond and Kelli Wilt, two full-time working homeschool moms at different stages of the journey, as they share honest, grace-filled advice for homeschooling young children. Whether you're just starting out or feeling stuck in the daily grind, this conversation is packed with wisdom you can use today. Kelli opens up about her early years of hypercritical self-assessment, thinking she had to prove homeschooling was the right choice by making her children the "best" at everything. She shares how God shifted her expectations and why extending grace to yourself, your children, and your community changes everything. The biggest victories often come in moments of vulnerability when you realize you're not alone in the struggle. Discover why trying to recreate the classroom model at home feels like wearing shoes that are half a size too tight, and how embracing the discomfort of something new leads to a beautiful fit for your family. Learn why rhythms and routines beat rigid schedules every time, and how to build in margin for those big feelings that little people (and big people!) experience.
This episode of Everyday Educator is sponsored by:
Online Learning Seminars
Online Learning Seminars offers live, interactive courses taught by CC graduate parents
who are experts in their fields. Ranging from four to six weeks and approximately 1.5 hours
of instruction per class, OLS offers a variety of courses including academic subjects that
align with classical education principles. While some courses focus on practical skills, all
courses are approached from a classical perspective of lifelong learning. Whether you want to learn something new or share your expertise as an instructor, join our OLS community today!
2026 Spring course offerings are open. Learn more by going to https://classicalconversationsinc.regfox.com/ols
Summit Ministries
Do you want your child to have conversations that challenge, encouragement that endure,
and friends and faith for life? Summit’s Student Conferences equip young Christians with
the hope, clarity, and confidence they need to follow Jesus boldly in today’s world. It’s not
just about getting apologetics answers. Students learn how to live winsomely and bravely in today’s world.
Visit summit.org/cc before March 31, 2026, and lock in the early bird rate. Save an additional $250 when you use the code CC26. Want your child to have conversations that challenge, encouragement that endures, and friends and faith for life? Grab their spot now at summit.org/cc