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)

Admittedly, today's world is far from the Garden where the world began.

If we think of our vocations as "recovering the Garden," we may wonder whether it is best to go out into the world with a missionary spirit or retreat to morally safer spaces and protect the flame. Which has the better impact on the world and our families? Can one go into the world and not lose his soul? And what does the world really need from us?

In his annual Headmaster's Lecture, Alvaro de Vicente encourages us to encounter the world with Christian confidence. We win it back through our families and professional work—and we should prepare our sons to do the same. For, Mr. de Vicente argues, there is no tension here: going into the world to serve with a Christian spirit is good for the world and good for the man.

3:52 Our sons going into the world
6:11 The world: God's gift to man
13:15 Sin: breaking the gift
18:32 Christ: redemption of the gift
20:42 Evil resides where good leaves
28:81 Winning back the world
30:12 How the Church views worldly professions
39:56 What work is for
42:30 The limits of "good" work
48:19 Good work is formative
50:22 Encouraging the next generation

"Chapter V: The Manners of the Christians" in Epistle to Diognetus by Mathetes

Forty Gospel Homilies by Pope St. Gregory the Great

The Way of the Cross by St. Josemaría Escrivá

Gaudium et Spes pastoral constitution by the Second Vatican Council

The World Needs Your Son to Be Professionally Ambitious by Alvaro de Vicente

Elon Musk, Mother Teresa, and Why Catholic Schools Should Be Secular by Nate Gadiano

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)

This fall marks the 25th anniversary of the institution of the Heights Clans. These competitive bodies engage in festivity six days a year, including two full Clan Days every All Saints Day and Feast of the Annunciation. This participates in the rich liturgical and intellectual traditions of authentic feasting, using the building blocks of worship, arts, food, and games.

Today on HeightsCast, middle school teacher and clans gamemaster/meister Kyle Blackmer explores why a school—or any community—should consider a commitment to these rituals of festival.

4:28 Pieper's definition of festival
7:33 Each festival unique to its place
9:01 Heights Clan Days
15:03 Why feasting is important
20:43 Connecting a student body
22:19 A liturgical basis
24:28 Preparation: the fast before the feast
28:21 Practical challenges to festival

The Heights Student Life: Clans, containing more information about our four clans and clan festival days

In Tune with the World: A Theory of Festivity by Josef Pieper

"The Immortal Power of Astonishment and Laughter" by G. K. Chesterton

Around the Year with the von Trapp Family by Maria von Trapp

The Life of Christ by Fulton Sheen

In Defense of Victory by Kyle Blackmer

Headmaster's Lecture at The Heights School (October 3, 2026)

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)

At The Heights, every teacher functions as a mentor for students. This is more than a figure of speech; it's the character of certain student-teacher relationships with routine check-ins oriented toward holistic personal growth. This week on HeightsCast, Headmaster Alvaro de Vicente considers the scope of different kinds of advisory, and outlines his vision for what makes real, effective mentorship.

4:36 Whether all teachers are mentors
9:07 All advisory: goals, agency, and disposition
12:40 Spiritual direction and coaching
16:29 The scope of our mentoring program
20:20 Primary relationships for growth
23:17 Secondary supports for growth
26:49 A holistic mentor
28:23 Mentees of another faith
31:06 Handling big questions

The Heights School Mentoring Program, including links to the mentoring handbook and topics by age

Mother Teresa, Come Be My Light: The Private Writings of the Saint of Calcutta by St. Teresa of Calcutta

The Mentoring Playlist on The Heights Forum, containing essays and podcasts on the topic

Headmaster's Lecture at The Heights School (October 3, 2026)

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)

There's a sea of online math supplements, from drills to games to whole courses, all promising advancement for your struggling student (or your stellar student who has outpaced his cohort). What kind of program, if any, is right for your student? Under what conditions are digital tools most effective?

Heights math teacher David Maxham gives us an extremely practical guide to the best digital resources out there and how to use them effectively. He also shares the failure modes you may not see coming when "hiring" a digital tutor for your child.

2:19 Digital tools at a liberal arts school
3:47 For students at both ends of the spectrum
11:41 Online drills: assisting academic virtue
14:12 Parent guidance still needed
18:56 Benefits of in-person lessons
23:32 How digital data can help teachers
27:08 Getting student buy-in, gaining confidence
32:22 Whole online courses: Math Academy over Khan
41:44 Remediation without embarrassment
46:46 Common pitfalls to outside help

Math Facts Lab drills, broadly recommended by Mr. Maxham

Rocket Math drills, also mentioned

Math Academy courses, recommended by Mr. Maxham

Khan Academy courses, Mr. Maxham says best as a supplement, not as a class

Matific, gamified math practice

Beast Academy

The Digital Delusion: How Classroom Technology Harms Our Kids' Learning—and

How to Help Them Thrive Again by Jared Cooney Horvath

Automaticity and Creativity by David Maxham

Automaticity: Where 'Rote' Fits into the Liberal Arts featuring David Maxham

How to Help Your Son When He Struggles Academically: Part I by Michael Moynihan

How to Help Your Son When He Struggles Academically: Part II by Michael Moynihan

Headmaster's Lecture at The Heights School (October 3, 2026) – link coming soon

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

Fatherhood Conference at The Heights School (early November 2026) – link coming soon

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

How do we know whether we know something? How do we know whether our son or student has apprehended a lesson?

Sometimes we hear the liberal arts discussed as a "beholding of great things." But Catholic University professor Dr. Jonathan Buttaci reminds us they are liberal arts—implying a craft or adept handling of knowledge. In other words, coming to know something is not passive at all. It's an act. And that act does not primarily belong to the teacher.

This week on HeightsCast, Dr. Buttaci talks epistemology and what the role of the teacher really is in bringing young people to knowledge.

3:59 Knowledge: active, not passive

12:56 Practical ends of knowledge

18:02 Contemplation: Buttaci v. Pieper

24:04 Liberal arts

30:16 Knowing bestows freedom

35:29 Where truth and creativity meet

42:27 The power of the teacher

43:52 How teachers can preserve the joy of discovery

57:59 Teaching rote, grindstone skills

01:05:08 A teacher's job is joyful

Education Is Not about Content Transmission by Dr. Andrew Abela, notes on a presentation by Dr. Jonathan Buttaci
Magnifica Humanitas, papal encyclical by Pope Leo XIV
Leisure: The Basis of Culture by Josef Pieper
The Idea of a University by John Henry Newman

Automaticity and Creativity by David Maxham
Automaticity: Where 'Rote' Fits into the Liberal Arts featuring David Maxham
The Teacher's Voice featuring Tom Steenson
Teaching Sovereign Knowers Series by Michael Moynihan

Headmaster's Lecture at The Heights School (October 3, 2026) – link coming soon

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

Fatherhood Conference at The Heights School (early November 2026) – link coming soon

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

The most famous work of our newest Doctor of the Church is, of course, The Idea of a University—a collection that explores the essence of a Catholic university education. But fewer people know about St. John Henry Newman's extensive efforts in primary and secondary education:

Newman's part was not just as an educational theorist, but a school founder, who played every nitty-gritty role from fundraising to parent relations, from essay grading to student mentoring, even processing repair orders and playing second violin to fill out the little school's orchestra.

Dr. Paul Shrimpton has spent decades studying Newman's interest in education, from theory to practice. Today on HeightsCast, he invites us into Newman's vision for younger students, their teachers, and grammar schools as places of "grounding" and "a really liberal education."

00:05:18 Co-patron of the Church's educational mission
00:07:50 Timeline of Newman as educator
00:20:25 Different models of student freedom
00:27:39 Methods of study for young people
00:34:11 Newman: a personal, hands-on educator
00:39:26 The role of a teacher
00:48:23 Partnership with parents
00:57:39 Forthcoming book on Newman: education and practice

"Drawing New Maps of Hope" apostolic letter by Pope Leo XIV
The Idea of a University by John Henry Newman
Historical Sketches, especially vol. 3, by John Henry Newman
"Personal Influence: The Means of Propagating Truth" by John Henry Newman
The Adeodatus Series on Catholic Education & Culture by The Catholic University of America Press (publisher for Dr. Shrimpton's forthcoming book, St. John Henry Newman and his Idea of a School, spring 2027)

A Catholic Eton?: Newman's Oratory School by Paul Shrimpton
The Making of Men: Idea and Reality of Newman's University in Oxford and Dublin by Paul Shrimpton
The Most Dangerous Man in England: Newman and the Laity by Paul Shrimpton

A Whole Education: Teaching Persons, Not Just Subjects featuring Michael Moynihan

The Idea of a Catholic University featuring Dr. Peter Kilpatrick

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

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

"Friendship is one of the most indispensable requirements of life," says Aristotle in the Nicomachean Ethics. But, adds Alasdair MacInytre, it's also "difficult and often enough impossible—especially under the conditions characteristic of contemporary modernity."

Today on HeightsCast, long-time colleagues (and friends!) Austin Hatch and Tom Steenson reflect on the nature of friendship, and why it was chosen as the theme for the 2026 Convivium Conference for Teaching Men, hosted by The Heights Forum this November.

What is the value of friendships among fellow faculty? What are the ingredients of that friendship? How should individual teachers seek it? How can school leaders foster it? And how might the students benefit?

Mr. Hatch and Mr. Steenson begin to scratch the surface of these questions in preparation for the deep-dive at this year's Convivium. If you'd like to join us, registrations, essays for the conference companion, and proposals for breakout sessions are now being accepted.

7:42 Aristotle and Cicero on friendship

12:46 Teaching: a shared life

16:09 Friendship: shared work, shared mission

20:31 Time constraints to friendship

24:50 Faculty friendship's effect on students

32:41 Maintaining culture as the school grows

38:34 Education: a raising of friends

44:24 Best practices for school leaders, individual teachers

De Nicola Center for Ethics and Culture Keynote: Is Friendship Possible? featuring Alasdair MacInytre

"Economy and Pleasure" in The Art of the Commonplace by Wendell Berry

Faculty of Friends: Making Schools into Communities featuring Tom Cox

Friendship for Fathers: John Cuddeback on Living and Teaching the Art featuring Dr. John Cuddeback

On Hiring Teachers: Drafting a Faculty of Friends featuring Alvaro de Vicente