Freedom in the Upper School

The Art of Teaching: A Conference for Teaching Men


November 9-11 • The Heights School, Potomac, MD

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What does freedom look like in The Heights Upper School?

Having arrived early to the Easter Vigil, I found myself pondering this in a dark church.  The thought occurred to me as I looked up through the darkness: the freest man in the world is pinned to that cross.  What does that mean for us?  What does it mean for our children and their education?

While freedom defines The Heights, it manifests differently in each division of our beloved School.  In the Lower School it’s especially obvious in its visible, more physical dimensions: snowballs fly, so do boys; trees laden with lads; forts, fort wars, short-lived fort truces, subsequent broken truces and more fort wars; sticks, stones, tires.  If your son is here, you know what I’m talking about. 

In the Middle School, as boys begin to age up and out of boyhood, that visible extrinsic freedom remains though its expression begins to take on a more subtle hue.  Tackle football at recess, snowballs still a’flyin’; cooking over an open fire; rafting down the raging Youghiogheny River.  Yet there is a physical self-restraint that begins to emerge: perhaps the fruit of a burgeoning temperance; more often a symptom of an erupting social self-consciousness.  Visible manifestations of freedom are there nevertheless.  You can still see the boy allowing himself to be what he is; to live a rough, tumble, tactile, slaphappy phase of life that he must experience to fully become what he is made to be.

The Upper School Transition

Boys in the Upper School live and experience their freedom in a different manner.  Snowballs fly, but less frequently.  A seriousness emerges that, on occasion, expresses itself on studious brows.  Our boys are now playing for keeps and it shows.  College appears to freshmen over the distant horizon.  Playoffs and championships enter the athletic experience, along with the losses thereof.  Relationships, both with one’s peers and with those of the opposite sex, consume more time and attention as our youth strive to find their place.  Separate from these quintessential high school experiences, a question dawns for our boys:  “what am I going to do with my life?”

Thus emerges something of a paradox: there are far fewer external restraints upon our Upper School boys, yet the apparent self-restraint visible in the hallways hits its peak.  True, our boys have lives outside of School, but here, in the academic domain, we see a more purposeful stride and an ever increasing self-mastery.  This is especially the case when the lads pass the sophomoric phase of life, marching into 11th grade and an age that appears far more transformational than the 9th grade our cultural powers have chosen as the beginnings of young adulthood.

How, then, is freedom experienced in our Upper School?  And how is freedom lived in an institution devoted to imparting the arts of liberty?  These are massive questions that we can only begin to answer here, but we’ll hazard an introduction.

Freedom to Question

Education, as the philosophers say, is not a matter of filling a vessel, but of lighting a fire.  And questions fuel the fire.  Accordingly, our students are free to ask questions.

In our Upper School, students enjoy the freedom not just to speak freely—itself a privilege now on the wane—but to ask freely as well.  Students share what troubles, puzzles, perplexes and befuddles them, either in a classroom setting or privately with their mentors.  These inquiries—when sincere—are a gift to the teacher who is given the opportunity not just to inform, but also to direct and shape the heart and mind of the man-in-the-making.  In so doing, we reach beyond the substance of present questions, and take on the task of shaping the mode and manner of future inquiries.  Give a man a fish, feed him for a day; teach him to seek truth, feed him for a lifetime.

In addition, a boy’s questions carry priceless insights into his interior disposition.  What troubles him?  What assumptions does he make?  What is it in his experience that might lead to that question in the first place?  Ask a boy what he believes to be the most important things in life, and you’ll get an answer that might be totally sincere, but profoundly inaccurate as to his own mental state.  He’ll want to get that answer “right,” of course, so he might go with Aristotle, or Cicero or the Ten Commandments; perhaps “happiness” or, the catch-all: Heaven.  Obviously, as teachers we have to ask deep questions, partly because we want the boys to get in the habit of seeking these truths themselves.  But if you really want to know what makes a student tick, you might be better served by listening to his questions rather than his answers.  Here we see what he really believes to be the measure of a man’s success, the meaning of life, the purpose of his efforts, and whether or not he believes himself to be worthy of love.

The ability to question is particularly important during the Upper School years, when students seek to own what in the past they might have been told to believe.  Sheer imposition, in the mind of a red-blooded male, can belie a lack of clarity in the truth thus imposed.  Caution, lest our students nod vigorously as they secretly doubt, and smoldering questions unasked in the present ignite at a later date when our boys are beyond us—not necessarily our supervision and control but, more importantly, our friendship and guidance.

And so, we ask our boys to ask us questions.  As long as the intention is pure and sincere, directed to the pursuit of understanding, all inquiries are welcome.  Why does the church teach such-and-such?  What do we think of Mssr. Will Smith defending his wife’s honor?  Again, all questions welcome, including the contemporary, and especially the popular.  Celebrity questions, even when asked in jest, can be flipped into meaningful conversations about timeless principles by a quick flick of the mental wrist.  All they wanted to talk about was Super Bowl commercials or Snoop’s halftime show; next thing they know, they’re discussing marriage and the common good.

Nota bene: we don’t subscribe to the “question everything” mentality, and we certainly don’t “question reality” itself.  On the contrary, we seek because we know the truth to be, and so do the boys.  They know this intuitively, as most of us do.  Even their emotive responses to certain hypotheticals contain a beautiful germ of truth in a nascent sense of justice, or a restless heart longing for a place to rest.  While these hearts must be directed and honed, we want our boys to be passionate.  Our openness to questions (and perhaps our answers too) can provide this direction.

Besides, questions make for more fun in the classroom.

Freedom to Form Friendship

At The Heights, friendship is just as foundational as freedom.  

Does friendship lead to freedom?  Does freedom lead to friendship?  Both/and?  That’s what I call a “lunch question” in my AP Gov class.  Regardless, this amicitia bears a place of honor at our School, even serving as the motto of the Red Rose Clan.

Granted, friendship (and asking questions, for that matter), are prominent characteristics of the lower and middle school experience.  Unquestionably, authentic friendship can and does begin to germinate in our lower grades.  Yet there is a marked difference between a childhood friendship rooted in common experience, a boyish friendship rooted in utility, and a young man’s friendship rooted in love.  

But as our boys hit high school, and in a special way—once again—when they hit 11th grade, we begin to see green shoots of authentic friendship rooted in mutual love of each other and the good.  It is one (priceless and infinite) thing to go to Mass; it is another (priceless, infinite, and then some) to go to Mass accompanied by your friend.

Freedom to Dress as a Dinosaur on Halloween with Mr. Hude

These sorts of friendships, rooted in mutual love and a shared pursuit of the good, are invaluable.  As for me and my house, I might accept a mediocre curriculum (ours isn’t), a mediocre athletic program (ours isn’t), and a mediocre campus (ours isn’t) so long as my children have the opportunity to immerse themselves in a community that I know will at some point yield the type of friendships praised by the ancients.  That said, a community built on friendship in pursuit of the good can’t remain lackluster for long.  Our shared impulse, as friends, is to make something beautiful, which is why, as Fr. James Schall points out, “friendships of good men are the most likely sources of opposition to bad rule.”

At The Heights our students are free to become friends.  This freedom stems from the absence of generally present social constraints on friendship.  Similarly, it flourishes in the presence of catalysts to friendship that are increasingly hard to come by.  

The constraints we strive to avoid include, among very many other things, the device.  Admittedly, Heights families take a variety of approaches to screens and this accounts, in part, for the varying levels of benefit drawn from the education we offer.  But the fact remains that, in general, personal devices are stowed away between 8:20 and 3:00.  Our expectation is that if you want to check your phone, you’d better do it in a private place, away from the public square.  For this reason, our public square remains a place where spontaneous conversations happen and friendships can be formed.  Our boys are free to talk directly to each other.  Even when it’s awkward.  Especially when it’s awkward.

And the catalysts to friendship abound.  In addition to the opportunities for adventure and athletics that are naturally conducive to male bonding, our boys enter friendships because they share a core curriculum that gives them not only a common academic program to discuss, but also a common set of teachers whose strengths and quirks and foibles can be enjoyed, both now and years after graduation.  “Remember when ole’ Mr. So-and-So threw the marker?”  To have friendship, we must first have something in common, and at The Heights we introduce our students to a common heritage that can serve as the bedrock for beautiful friendships: both the great books and the teachers trying to be great who accompany the boys in their reading.

And conversation is, as Josef Pieper has written, where truth resides.  So our boys are able to converse freely.  They might use this freedom to chat about the latest Key and Peele (as a colleague pointed out in a video on The Heights), or they might discuss Ciceronian ethics.  Either way, our boys are able to speak their mind.  This is a freedom from the forces currently curating and censoring our speech; and it is a freedom for the liberating pursuit of a shared understanding, which, in the end forms a friendship between minds, souls, and hearts seeking together.

Make no mistake about it: on occasion we, the faculty, hear things we wish we didn’t in the hallways.  It should be no surprise that freedom is sometimes abused.  In fact, this draft was just interrupted by a fire alarm pulled on the third floor.  Why?  I’ll never know.  We confiscate cell phones and sometimes dummy phones too.  We impose lunch duties for misuse of freedoms that are given.  But better to offer that freedom and nurture its better uses, than to extinguish it along with the friendships it makes possible (my thanks to Mr. Madison for the metaphor).

A Freedom For

To conclude this first part of my reflection: the Heights man we all strive to become—liberally educated, of engaged mind, thick skin, and soft heart (as our Lower School Head says)—has the freedom to seek truth in friendship.  And if that quest, either today or many years hence, should require him to lay down his life for his friend, he is at liberty to do so.  He knows that love conquers all, and the silhouetted crucifix of the Easter Vigil marks the path for men free enough to be fully alive.

Stay tuned for Part II.

Rich Moss

About the author:

Rich Moss


Rich earned his B.A. and J.D. degrees, both Magna Cum Laude, from the University of Notre Dame, in 2005 and 2008 respectively. Prior to returning to his alma mater to lead its Admissions Office in 2010, Rich was an associate attorney in the Energy and Trial Practice groups of Jones Day in Washington D.C. While working as an attorney, Rich was also the vice-president of The Heights Alumni Association. During law school, Rich was an Article Editor for the Notre Dame Law Review. Rich graduated from The Heights in 2001. In addition to his work in the Admissions Office, Rich teaches AP US Government and is the faculty advisor to the Rock Climbing Club. He resides in Wheaton, Maryland and is a parishioner at St. Andrew Apostle in Silver Spring. When he’s not introducing new families to The Heights, you might spot Mr. Moss biking around Wheaton with his awesome wife and four youngsters, or climbing Carderock with his fellow Heights alumni climbing partners!