Podcast Episode Summary

Podcast: Hillsdale College Podcast Network Superfeed
Episode: Leading Seven Oaks Classical School
Date: September 4, 2025
Host: Scott Bertram, with the Head of School at Seven Oaks Classical School and other classical school leaders

Main Theme & Purpose

This episode presents a compelling account of what it means to lead a classical school, focusing on Seven Oaks Classical School in Indiana. The episode is drawn from a presentation delivered at a Hoagland Center for Teacher Excellence seminar, emphasizing the transformative power of classical education. The Head of Seven Oaks shares personal experiences, the mission of the school, and insights into the daily realities and responsibilities of leading a classical school. The second half includes voices from multiple classical school leaders and staff, illustrating the broader community and network supporting classical education through Hillsdale College.

Key Discussion Points & Insights

1. The Mission and Meaning of Leading a Classical School

[01:55–10:30]

• The Head of Seven Oaks introduces the school's origins and growth: from 160 students (K-8) in 2016 to 570 (K-12) today, serving a small town near Bloomington.
• The fundamental motivation for leading a classical school: "Most people want to do something meaningful...to participate in some noble work bigger than ourselves" (Head of Seven Oaks, 02:21).
• The mission: "Train the minds and improve the hearts of young people through a rigorous classical education in the liberal arts and sciences, with instruction in the principles of moral character and civic virtue" (03:18).
• The aim goes beyond academic preparation: It’s about “the cultivation of virtue,” or more broadly, “human excellence—intellectual, moral, and civic” (03:45).

2. The Content and Method of Classical Education

[04:30–06:40]

• Education is not merely about skills: “We are languaged beings, and we want to train our students to read well, write well, think well, and speak well… but the education is about far more than just skills” (Head of Seven Oaks, 05:08).
• Students are introduced to "the age-old conversations about truth, beauty, goodness, justice, friendship, love" (05:55).
• Importance of teachers: "They are a kind of living story...the students are reading them each day. This is a kind of story that unfolds" (06:35).

3. Personal Narrative: The Transformative Power of Education

[07:00–11:10]

• The head of school shares moving family stories, illustrating the intergenerational impact of education:
  • Grandfather: An immigrant who couldn't attend college but treasured education, ensuring his children could go.
  • Father: Escaped a cycle of poverty thanks to a mentor who believed college was possible.
• Personal experience: A childhood filled with books, which led to embracing the Western tradition in college, shifting his career goals from law to education: “I was absolutely blown away by the richness of the Western tradition. In a very real way, I felt myself lifted outside the narrow valley of my own experience” (Head of Seven Oaks, 09:09).

4. Why K-12? Schools as Seedbeds of Virtue

[11:20–14:30]

• Doctoral studies with Alexis de Tocqueville influenced the understanding that “the art of freedom has to be learned” through participation in local institutions like schools (11:40).
• Experience teaching at a classical Christian school revealed a collegial environment and deep purpose, paralleling the best aspects of university life, but with the added “gift of time” to walk with students over years (13:20).
• Reflection: Classical education today is similar to what was simply considered “education” in previous generations—content-rich and character-focused (14:00).

5. The Differences and Challenges in Modern Education

[15:00–16:00]

• Modern schools: Many have become “dominated by testing, stripped of content, and lacking a common vision for cultivating virtue...Our kids are missing an important help in growing as human beings” (15:15).
• Seven Oaks, as a public charter, is offering a type of education that most of its students wouldn’t otherwise access.

6. Stories that Illustrate Classical Education’s Impact

[16:20–19:40]

• The Power of Language:
  • A child reciting Robert Louis Stevenson’s poem The Swing while on the playground: “Poetry had given him a vehicle for awakening and giving expression to his inner life” (17:24).
• The Power of Love:
  • An alumna (Ariel) with family struggles who returned to Seven Oaks because she remembered “its teachers who loved her and wanted to help her grow as a human being” (18:25). She later graduated, became a social worker, and enrolled her sibling at Seven Oaks.

7. Calling, Purpose, and Legacy

[19:50–21:00]

• The leader sees himself as “a trustee, just one link in a long chain doing the work that many others do, trying to do my duty, to use the British phrase, to do my bit and pass along...what I’ve received and hopefully to pass it along with interest” (20:22).
• The work is sustained by gratitude for those who invested in his own education, his colleagues, and ongoing partnership with Hillsdale.

8. The Daily Work and Community of Classical School Leadership

[21:03–26:58]

• The Daily Realities:
  • “No day is the same... You think you know what your calendar is. It’s very rare that the day unfolds exactly like that” (Classical School Leader, 21:15).
  • The leader is “the shepherd of the school’s mission and culture. There are no two things that are more important than that” (School Principal, 22:12).
  • “My goal is to be as visible as possible...walking the hallways, coming into classrooms, spending time with students, holding virtue-based conversations” (Podcast Host, 21:35).
• The Demands:
  • “The principal is truly responsible for everything that happens on the ground” (Scott Bertram, 21:29).
  • “You meet with your board, interested parents...other grade levels, all articulating the same basic thing: that education deserves their attention, and it’s a good thing” (Head of Seven Oaks, 21:58).
• Diverse Backgrounds:
  • Some leaders are academics; others come from the military or other vocations.
  • “I served in the Air Force for 24 and a half years... I realized I could continue to honor that oath...by shaping the next generation of citizens” (School Principal, 23:03).
• The Role of Hillsdale College:
  • Provides “mentoring, guidance, tons of resources,” including training, conferences, and connections to a network of like-minded schools (Scott Bertram, 23:48, Head of Seven Oaks, 24:39).
  • Leaders form a “community of friendship” and professional support (Classical School Leader, 23:48).
• Impact on Students:
  • A principal recounts a boy who, after a rough start, said: “I had to use perseverance to get through it”—evidence of internalized character growth (School Principal, 26:58).

9. Final Reflections

[26:01–28:03]

• “There’s no more significant thing that one might do than become the leader of a classical school. Today we are powerfully in need of good examples because it just matters so very much” (Scott Bertram, 26:01).
• The impact of school leadership: “The futures of 800 little people depend on the decisions that I make… and the example that I set” (Podcast Host, 26:24).
• Despite the difficulty: “This journey is one of the most difficult things that I’ve ever done, but it is absolutely worth it. If I could do it all over again, I would jump into it” (Classical School Leader, 26:38).

Notable Quotes & Memorable Moments

• “We have a duty to give every child of every generation the best education that we can.”
  — Head of Seven Oaks Classical School, [01:59]
• “There’s something really beautiful and life-giving about working with children, but for the classical educator...there’s also kind of an awesome added weight of responsibility because we think that we actually have a part to play in the formation of children’s souls.”
  — Head of Seven Oaks, [02:49]
• “Education isn’t just about skills. At the end of the day, it’s an education focused on helping students know and love what is excellent.”
  — Head of Seven Oaks, [05:12]
• “I was absolutely blown away by the richness of the Western tradition. In a very real way, I felt myself lifted outside the narrow valley of my own experience.”
  — Head of Seven Oaks, [09:09]
• “The school prepares kids for liberty...in the little commonwealth of the classroom, there are all kinds of other lessons being learned.”
  — Head of Seven Oaks, [12:02]
• “I have the added satisfaction of knowing that the kind of gift that we’re giving with a classical education is something that most of our students would not have the opportunity for but for the presence of our school in that community.”
  — Head of Seven Oaks, [15:47]
• “Poetry had given him a vehicle for awakening and giving expression to his inner life.”
  — Head of Seven Oaks, [17:24]
• “I see myself as a trustee, just one link in a long chain doing the work that many others do, trying to do my duty.”
  — Head of Seven Oaks, [20:22]
• “You wake up and you think you know what your calendar has lined out for you. It’s very rare that the day unfolds exactly like that.”
  — Classical School Leader, [21:15]
• “The main purpose of a headmaster is to be the shepherd of the school’s mission and culture.”
  — School Principal, [22:12]
• “My dream is inspiring and encouraging a lot of new leaders...and I hope that we can work together to revive America’s education.”
  — Classical School Leader, [25:43]
• “The work is so important because the futures of 800 little people depend on the decisions that I make in each day and the example that I set.”
  — Podcast Host, [26:24]
• “I had a really tough time in math and I had to use perseverance to get through it. I just about cried. He would have never ever said anything like that at the beginning.”
  — School Principal, [27:07]

Timestamps for Key Segments

• [01:55] — Introduction: The mission and growth of Seven Oaks
• [03:18] — The mission statement and central importance of virtue
• [05:08] — The vision for classical education: language, skills, and beyond
• [07:00] — Family history and the transformative power of education
• [11:40] — Tocqueville on schools and liberty
• [17:24] — The poetry anecdote (“The Swing”) and awakening of the inner life
• [18:25] — Ariel’s story: love and belonging in classical education
• [21:15] — Daily leadership realities in classical schools
• [22:12] — “Shepherd of the school’s mission and culture”
• [23:03] — Backgrounds of school leaders: academicians, military, and more
• [24:39] — Support from Hillsdale College: training, mentoring, and community
• [26:01] — Final reflections: the great need for good school leaders
• [27:07] — Story of perseverance in a student

Flow & Tone

The tone remains earnest, reflective, and deeply committed throughout, mirroring the underlying seriousness and hopefulness of classical education’s enterprise. Personal stories add warmth and relatability, while the leaders’ voices convey dedication, humility, and gratitude.

This episode provides a window not just into the day-to-day and larger mission of leading a classical school, but into the philosophies, personal journeys, and community support that animate the broader classical education movement.