This age of AI puts a spotlight on the differentiated power of "thinking well." But the best way to teach students to think well is counterintuitive: we have to be willing to make mistakes. Students and teachers alike will have to get comfortable with the idea of mistakes as part of the journey toward critical engagement.

In this week's episode, music teacher Pat Love and middle school teacher Shane O'Neill liken education to good jazz. Students absorb the traditions, imitate the masters, try to make it their own, and learn by trial and error under a trusted guide.

2:37 The jazz and education analogy
7:50 Making space in the classroom to try—and fail
9:46 Teacher habits for student agency
15:21 Tests, assignments, seminars
18:54 The educative power of imitation
22:42 Grades, and when a kid is "playing scared"
27:43 Turning correction into learning
31:07 Fewer one-right-answers
37:06 Drawing out participation
41:48 Transmitting a culture, not just a subject
43:58 Addressing philosophical mistakes

The Risk of Education: Discovering Our Ultimate Destiny by Luigi Giussani

The Art and Act of Knowing—and What It Means for Teaching featuring Dr. Jonathan Buttaci

Educating Boys: Nature, Risk, and the Making of Men by Dr. Joseph Lanzilotti

Teaching Sovereign Knowers Series by Michael Moynihan

Fall Open House at The Heights School (October 24, 2026)

Fatherhood Conference at The Heights School (November 7, 2026)

Convivium Conference for Teaching Men at The Heights School (November 11-13, 2026)