Father Nathan Carr, Headmaster of The Academy and often dubbed “the Jack Sparrow of classical education,” joins Christopher Perrin to recount his unexpected path into classical Christian school leadership—and the hard-won lessons of building a flourishing school culture over two decades. Their conversation draws on James K. A. Smith’s Desiring the Kingdom to argue that “liturgies” (in church and in culture) quietly train our loves and longings. Carr connects that insight to his own work, The Festive School, where he explores how a school’s calendar, habits, and celebrations can become formative—not merely decorative. He also points listeners to his Student Prayer Book as a practical companion for cultivating daily, embodied prayer in the life of a classroom. From The Book of Common Prayer and the daily offices to monastic rhythms like Matins and Compline, he frames education as formation through repeated, prayerful practice. Along the way, they address objections to “rote” ritual, suggesting that repetition can become spiritually alive and deeply consoling over time. The episode closes with concrete snapshots of festivity at The Academy: Lessons & Carols, Stations of the Cross, and campus-wide celebrations of Incarnation and Resurrection. Father Nathan Carr also has a forthcoming course on ClassicalU.com that will release in the early Spring of 2026.