Homeschooling Day in the Life: Ashley, Homeschooling Mom to One Middle School Child, Living in Massachusetts
A homeschool day in the life looks different almost every day, right? Over on our Instagram page, we love to give you a peek into lots of homeschool days regardless of how they change day to day.
Today, we’re going to give you a peek into the homeschool day in the life of Ashley, homeschooling mom to one middle school child, living in Massachusetts.
We can all learn and be inspired by one another, regardless of our homeschool approach. It’s not about looking good for social media, it’s about the connection going on inside our homeschool walls and sharing with others what works for us.
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We might all homeschool a little differently, but we can always look for ideas from each other that inspire, encourage and equip us in our own homeschool days. So each week we create blog posts for you to access later of each of those “days in the life”. We hope you keep coming back for more inspiration. Keep going, mama! These days at home are so worth it!
Meet Ashley
Ashley @thewoodsysort is a homeschool mom to an only child and Army wife of 18 years. She homeschools her middle schooler in Massachusetts where they’ve lived for the past year. Before that, they lived in Seoul, South Korea for three years.
On Instagram and Substack, Ashley shares honest reflections, helpful tips, and a whole lot of encouragement for fellow homeschool families. Her content invites others into a slower, more thoughtful way of life—rooted in wonder and truth.
The Structure of Our Days
Homeschooling an only child in the middle school years can feel like walking a path through a vast forest—beautiful, challenging, and full of unexpected moments.
We’re walking that path with Challenge A through Classical Conversations this year, and it’s brought a helpful structure to our days:
- Weekly seminar days with her class
- Independent map tracing (we use tracing paper + a good playlist)
- Latin review with flashcards
- Literature discussions, writing outlines, and practicing persuasive essays
- And a rhythm of daily checklists to help her manage her time
She meets once a week with her classmates, but most of her work happens at home—just the two of us. And while that’s a gift, it also takes intentionality.
This year’s theme—attention leads to ownership—has been lived out in real time. She’s learning how to plan her week, pace herself, and take initiative. I’m learning to step back a little, trust more, and let her figure things out—even if it’s not perfect. It’s not always neat or easy, but it’s good.
If you’re homeschooling a middle schooler, too, I’d love to hear what’s working in your home!
4 Books We Have Loved This Year
Some books just stick. We’ve read a lot this year, but a few titles have become instant favorites—ones we’ve underlined, quoted, and carried with us in conversation. Here are 4 books we loved in our homeschool this year:
- A Door in the Wall – A gentle medieval tale of resilience and finding purpose when plans change
- Beyond the Bright Sea – A lyrical mystery about identity, belonging, and the meaning of family
- The Bronze Bow – Rich discussion on courage, justice, and faith set in first-century Galilee
- Number the Stars – A moving story of quiet bravery during the Nazi occupation of Denmark
Whether it’s Morning Time or bedtime, reading aloud continues to be a core part of our homeschool. These stories have helped us think deeper, laugh harder, and grow closer.
Preparing for Testing
As we near the end of our first year in Challenge A, we’re beginning to prepare for Blue Books—Classical Conversations’ end-of-year assessment.
Blue Books are written exams that give students the opportunity to reflect on and articulate what they’ve learned in each strand—from Latin and Logic to Cartography and Literature.
It’s not a test in the traditional sense. There are no grades or scores. It’s more of a guided conversation on paper—an invitation to think deeply, to remember, and to respond thoughtfully.
We’ll spend time reviewing key concepts, discussing big ideas, and revisiting the work she’s done this year. And in the process, we’ll celebrate growth—not just in knowledge, but in confidence and character, too.
Long Walks-Essential to Discipleship
It was a full day today, so we missed our daily walk, but I really do believe long walks are essential to discipleship. I have found no better way to get her talking for forty-five minutes straight.
Something about the rhythm of steps and the absence of eye contact opens a middle schooler right up. Stories come spilling out. Questions surface. Worries find words. It’s not always profound, but it is consistent. These walks have become one of our best rhythms for connection and spiritual conversation.
If you’re finding it hard to connect with your middle schooler, try this: take a walk. Skip the curriculum for a bit. Just move and let them talk.
Thank You
Thank you for following along today—it’s been such a joy to share a glimpse of our day. Homeschooling an only child, walking through the Challenge years, reading good books, asking big questions… it’s all a little messy and very meaningful. Wishing you courage and curiosity in your homeschool journey. Let’s keep in touch over at @thewoodsysort!
Thank you so much to Ashley for sharing your family’s day with us!
