In this engaging conversation, Dr. Clint Brand introduces us to Scott Newstok’s book, How to Think like Shakespeare: Lessons from a Renaissance Education, which serves as a door to a larger discussion of the nature of liberal learning and its inherent paradoxes. Dr. Brand considers with Newstok “a few touchstones derived from the Tudor play of mind and some habits of Renaissance education that apply very much to the challenges” we face in our current moment. He also explores the paradoxes that Newstok proposes to his readers: that play emerges through work, creativity through imitation, autonomy through tradition, innovation through constraints, and freedom through discipline. And Prof. Brand fittingly concludes the conversation with Wordsworth’s “Nuns Fret Not at Their Convent’s Narrow Room.” Links of potential interest: Clint Brand, ed., St. Gregory’s Prayer Book Scott Newstok’s book, How to Think like Shakespeare: Lessons from a Renaissance Education C. S. Lewis, An Experiment in Criticism Josef Pieper, Leisure the Basis of Culture (with an introduction by T.S. Eliot) Aelred of Rievaulx, On Spiritual Friendship William Wordsworth, “Nuns Fret Not at Their Convent’s Narrow Room”