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When The Headmaster Of A Classical School Does Not Read Old Books

What do classical teachers want from headmasters?

They want both leadership and leeway, although just about every employee wants those things. They want brave administrators who aren’t afraid to discipline the sons and daughters of prominent families, although nepotism and favoritism are a vexation to employees in every line of work. Teachers want good pay and benefits, too, but good pay is a universal human desire. So what classical thing do classical teachers want from headmasters and principals?

Before I answer this question, let me tell you about someone I work with. By all accounts, I am a very slow reader, though I work with a fellow who read Laurus twice in the same time it took me to read it once. In the same time he was reading Laurus twice, he probably read more than four dozen other books, and not just contemporary works of fiction, but classics, some of which are part of the curriculum at Veritas, where we work, while others are just good old books he took an interest in for personal reasons. This fellow is not a literature teacher at Veritas, not a rhetoric teacher, not a history teacher. In fact, he is the headmaster of the school. Having worked at Veritas for six years now, I must say no small part of the school’s smooth operation derives from the fact the headmaster, the lower school principal, and the upper school principal are all committed readers of old books.

So, what classical thing do teachers want? They want headmasters and principals to be readers of classic books. This ought to be obvious, though, for it is the same thing classical teachers want from their students and co-workers.

And yet, a surprisingly high number of headmasters and principals at classical schools are not readers of classic books. I can’t point to a Barna Group study to back this claim up, but I have been to twenty classical conferences over the last ten years, and I have overheard and absorbed many lamentations from fellow teachers about headmasters and principals who see no point in reading the classic books they make their students read.

Granted, I have met enough headmasters (and heard about even more) who do read classics to know the problem isn’t ubiquitous. It would be horribly unfair to say most headmasters at classical schools don’t read classics. Nonetheless, the problem is far more common than an outsider would expect.

Why, though?

How can men and women responsible for the day-to-day operations of a classical school— an institution which deals in tradition, conservation, old books, old thoughts, discarded images, and worldviews abandoned long ago— have so little first-hand knowledge of their curricula?

I suspect classical headmasters who haven’t read much Augustine, Virgil, Homer, Dante, Milton, Plato, simply don’t believe such reading is necessary to do their jobs well. Rather, they think of classical education as a kind of theory or method— not a posture of the spirit— and so anyone who has read a few lately published books on the theory of classical education gets it. The best classical headmaster is thus one who marries a knowledge of classical methodology (Dorothy Sayers) with compelling theories of management (Stephen R. Covey). It is no more necessary for a classical headmaster to read Augustine than it is for a Wendy’s manager to read Dave Thomas’s autobiography.

Headmasters who don’t read classics talk about classical education in a very different manner than headmaster who do. Headmasters who don’t read classics are far more likely to claim a classical education is not concerned with teaching students what to think, but how. If it’s more about how than what, then how someone reads is more important than what they read. Thus, reading the City of God is not nearly as important as knowing how to read the City of God with a critical eye and a biblical worldview. While there are theological nutrients someone might gain from reading the City of God, those nutrients can be enjoyed just as well (if not better) from contemporary authors who distill great works of theology down to essential principles and presuppositions.

Of course, it’s possible for a classical school to have a headmaster who doesn’t read classics and for the school to generally run well, nonetheless. It is more important for teachers to read old books. Similarly, I know nothing about basketball, but I could probably coach a winning season if my starting five included Lebron James, Kevin Durant, and Stephen Curry. And it must be noted that a headmaster who has read the classics isn’t necessarily going to be good at his job, for he might be timid, bashful, easily distracted, or simply convey weakness and incompetence in a dozen other ways. A headmaster who reads classics must be capable of conveying a classical ethos to his faculty, staff, and students, as well. His love of truth, goodness, and beauty should typify faculty culture. If his love of classics is an entirely private affair, it won’t do his school much good, for most CCE teachers would rather have a non-classical headmaster with a spine than a timid headmaster who thinks Aquinas is neat.

And yet, the classical headmaster or principal who doesn’t read classics is also a huge liability. I will also make this wager: the fewer old books the headmaster or principal reads, the more political crises the school’s senior thesis program will create for the faculty. There must be a one-to-one correlation between schools with headmasters who don’t read classics and schools which regularly close out the year with dispiriting scandals involving theses judged “too Catholic.”


Ironically enough, the claim, “We train students how to think, not what to think” is a slogan, a dogma, a what. Simply put, it’s what the school does, not how. It is self-defeating nonsense, which means schools that claim to not train students what to think are ultimately embarrassed about their own demands and standards. It is far more common in how-not-what schools for a student to spend six years reading Boethius, Aquinas, Augustine, Dante, and Calvin, synthesize all they have learned in a thesis paper, then have their paper struck down, censored, or censured by authorities who don’t read old books, but don’t like the student’s conclusions. The how never really mattered. Ironically, the what is the only thing that matters at how-not-what schools— and the what is usually nothing more than a tidily packaged shibboleth.

I wish I could tell you that I am referring to a few bizarrely isolated incidents, but the fact of the matter is that classical schools all over the country have “too Catholic” thesis problems on a very regular basis. Of the half dozen faculty members near a senior with a “too Catholic” thesis, whoever is most high church will usually get stuck with the bill. Fake apologies follow, as do plans to adjust the thesis program next year so “this doesn’t happen again.” It all makes for a rotten, discouraging way of closing out the school year, yet these problems are easily prevented by headmasters who know the content of the old books their students read.


Anyone who has deeply read the City of God knows that classical education isn’t a method or a theory or a movement. Anyone who has read the City of God knows that a classical education begins in the vexed silence a man suffers after reading Augustine make a series of claims which he, the reader, does not like. This vexed silence comes from a place deep in the human heart. It is both emotional and intellectual. It is conceived when a man understands that Augustine is Augustine and he is not. Augustine’s works have lasted sixteen hundred years, but his works will not.

There are people smarter than you, and they all believe Augustine is smarter than themselves. Augustine read the Bible more than you do. You get bored reading the Bible and go make yourself a sandwich after ten minutes, then think about television. Augustine came to different conclusions than you, but he also read the Bible more than you do.

A classical education begins the moment Augustine’s love of the Bible makes you wish you loved the Bible more than you do. Your feelings about Augustine’s weird theology really don’t matter.

A classical education begins when your vexation with Augustine passes and you’re glad you don’t really matter.

A classical education begins when you realize the whole universe is a hierarchy— not a top-heavy hierarchy which keeps you down, but a ladder you were meant to climb.

Naturally, the value of a headmaster who reads classics extends far beyond senior thesis presentations. Any teacher who uses classic texts to robustly encourage students to pursue virtue will regularly be accused of preaching works righteousness, but a headmaster or principal who has read Dante will know how to handle such accusations. If the principal has read Dante, he will understand just how confusing, controversial, and downright offensive most American Christians find the idea of “cultivating virtue.”

Accordingly, principals and headmasters who read classics will be less likely to ride teachers about bumping every 89% to a 90%, for they understand classical education is no more a movement than Autumn is. There is nothing which crushes the spirit of a teacher quite like having an administrator step in just before report cards come out and demand that certain students be given higher grades for diplomatic, economic reasons— but until a principal has read Dante’s Comedy or Augustine’s City of God or The Consolation of Philosophy or the Summa, he will not truly understand why his requests that certain students get a point here or there bothers teachers so much.

I pray these final thoughts do not come off as the rantings of an idealist. Really, I have too much love for the book of Ecclesiastes to be an idealist. It is the headmaster’s responsibility to keep the lights on and this often involves compromise, for even Solomon complained that kings rarely get their own way. What is more, I am content that, as a teacher, my vantage point is not simply far different, but far less than the vantage point of the people who pay the bills. “I myself am a man under authority, with soldiers under me.” As such, my final appeal is to good old-fashioned curiosity. A fantasy, perhaps.

To all the classical headmasters out there who don’t read classics, don’t you wish you did?

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