Parents often wonder if pushing through difficult books is worth the tears and late nights. In this episode, Davies Owens is joined by Sara Osborne, author of Reading for the Long Run, as she explains why classics feel hard, how to discern real obstacles from attitude or context, and practical steps to move forward with confidence.
🎧 Tune in to hear:
- Why classics challenge modern readers, and why the challenge is good for minds and hearts
- How to make an honest assessment: simple journaling, patterns to watch, and assembling a “team of knowers”
- The start-small strategy: short, rich texts, repetition, paired audio, and building stamina like training for a race
- Respectful bridges for older students that avoid “babyish” materials, including short stories and thoughtful fables
- Tech, timing, and motivation: shaping habits that support deep reading at home and school
- The telos of reading: from “checking the box” to a lifelong love of truth, beauty, and goodness
- Weakness and formation: how pushing through hard things shapes character for students, parents, and classrooms
With honest assessment, small wins, and steady practice, any family can grow a reading life that lasts. If this episode encouraged you, share it with a friend, then try one simple step this week, such as a short story with paired audio or a five-minute read-aloud after dinner.
Resources Mentioned:
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The Herzog Foundation
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Wilson Hill Academy
Life Architects Coaching

Sara Osborne is the author of Reading for the Long Run: Leading Struggling Students into the Reading Life and currently serves as Assistant Professor of English and Director of Classical Education at College of the Ozarks in Point Lookout, MO, where she has taught for the past 13 years. She is the mother of four classically educated children—one now a sophomore in college, and three who currently attend School of the Ozarks, the College’s classical Christian lab school. When she isn’t teaching in the classroom or at home, Sara enjoys writing for a variety of venues on topics such as classical education, theological reflections on literature, nature, and travel.
Sara is passionate about teaching and learning and has been transformed by the challenge of educating students with disabilities or differences that make learning exceptionally difficult. She considers it a privilege to be an encourager and advocate for those who wonder if the end is worth the effort for such students and spends her days reminding herself and others: yes, it is.
Connect with Sara: