The Lessons of Sleepy Hollow: Musings on Classical Schools and the Teacher Shortage

There has been much talk of late about the hiring problems of classical Christian schools. Erik Twist’s recent article deals extensively with what might be called the “misconceptions” about how classical Christian education (CCE) institutions should approach the matter. Though Erik uses terminology from the modern corporate landscape, his concerns boil down to things schools should take seriously: hiring faculty who believe in the good of the classical model, a culture that supports and encourages new teachers, and the need for schools to take their purpose seriously so that others will do likewise. But of all of Twist’s points, the one that seems to have gained the most attention (at least on social media outlets like the website-formerly-known-as-Twitter and Facebook) is the problem of teacher salaries.  

Of course, this isn’t a problem unique to classical Christian schools, just as the teacher shortage isn’t unique to them either. Between teachers retiring and simply quitting, public and private schools of all kinds have struggled since COVID ended. And much of the conversation has revolved around teacher burnout. But something else that all schools have in common—the community that surrounds them—might best be reckoned with by considering what Washington Irving’s schoolmaster, Ichabod Crane, and the school community he led in Sleepy Hollow might have to teach us on the topic. 

So what might a short story from the early 1800s have to say about classical Christian schools and their communities in 2025? 

My own experience first meeting Ichabod Crane is probably a common one. In fourth grade, at a small public elementary school in a rural community, my teacher showed us the Disney animated adaptation of “The Legend of Sleepy Hollow.” The original short story by Irving was part of the textbook unit we were studying at the time, but the writing was believed to be a bit much for our fledgling minds. Instead, we watched the cartoon and moved on. On a whim, I spent our reading time later that day pouring over the story in the book and found that I loved it. The tale has stuck with me over the intervening thirty or so years, and I’ve often returned to Irving in the classroom and for my own pleasure. But no matter how many times I read the harrowing escape of Ichabod Crane, I’m always struck by how Irving could work so much into such a little story. 

One of the most overlooked aspects of Ichabod’s adventures is Irving’s educational commentary. Ichabod is, after all, the sole pedagogue of Sleepy Hollow, and there are plenty of comments throughout about things that remain relevant to teachers in the twenty-first century, such as parent relationships, pay scale, and student values. And the end of the story happens to coincide with an all too familiar chain of events that happens in classical Christian schools today. No, not the horrifying chase across the bridge by the Headless Horseman. Rather, CCE groups would do well to think about where Ichabod goes once he leaves the school and the circumstances that precede his midnight ride. 

Much of Ichabod’s story stems from the facts concerning his role as the local schoolteacher in a town that doesn’t consider education something to be overly concerned with. While it was true that Ichabod is “generally a man of some importance in the female circle of a rural neighborhood; being considered a kind of idle, gentlemanlike personage, of vastly superior taste and accomplishments to the rough country swains, and, indeed, inferior in learning only to the parson,” it is also true that “his rustic patrons . . . are apt to consider the costs of schooling a grievous burden, and schoolmasters as mere drones . . . .”  

And so, Ichabod develops “various ways of rendering himself both useful and agreeable” to lighten this burden, including “[helping] to make hay, [mending] the fences, [taking] the horses to water, [driving] the cows from pasture, and [cutting] wood for the winter fire.” Crane constantly had to justify his contribution to the town over and above his vocation. That still wasn’t enough to sustain him, however:  

[Ichabod] would convoy some of the smaller [students] home, who happened to have pretty sisters, or good housewives for mothers, noted for the comforts of the cupboard. Indeed, it behooved him to keep on good terms with his pupils. The revenue arising from his school was small, and would have been scarcely sufficient to furnish him with daily bread . . . [and] he was, according to country custom in those parts, boarded and lodged at the houses of the farmers whose children he instructed. With these he lived successively a week at a time, thus going the rounds of the neighborhood, with all his worldly effects tied up in a cotton handkerchief.  

Irving does say that Ichabod was able to make ends meet in the end by taking on “in addition to his other vocations” a little singing school where he “picked up many bright shillings by instructing the young folks in psalmody.” And as a result of working in the schoolhouse, on the community farms, and in his own voice studio, “the worthy pedagogue got on tolerably enough, and was thought, by all who understood nothing of the labor of headwork, to have a wonderfully easy life of it.”  

As the story goes, Ichabod vanishes one night, leaving the village without a teacher to keep their school humming along. The villagers, a superstitious lot, collectively agree that Ichabod must have been carted off by the local malignant spirit, a natural consequence for someone out too late at night. In response to their disappearing educator-in-residence, the parents in the community follow after the venerable town leader Hans Van Ripper, “who, from that time forward, determined to send his children no more to school, observing that he never knew any good come of this same reading and writing,” and thus, “the schoolhouse being deserted soon fell to decay.” When the townsfolk learn that Ichabod “had changed his quarters to a distant part of the country; had kept school and studied law at the same time; had been admitted to the bar; turned politician; electioneered; written for the newspapers; and finally had been made a justice of the Ten Pound Court,” the good people of Sleepy Hollow find it easier to believe that Ichabod had been spirited off by the Headless Horseman than that he had found success outside the classroom. 

An easy life of it, indeed. 

C. S. Lewis, that eminently quotable saint of Christian education, once noted, in The New York Times of all places, that “it certainly is my opinion that a book worth reading only in childhood is not worth reading even then.” While “The Legend of Sleepy Hollow” may be relegated to middle school reading groups today, I’d suggest that there are things in the tale that merit a further look at age twenty, age forty, and beyond.

And for teachers of any age, it can be easy to read Irving’s tale and begin wondering, “am I an Ichabod Crane?” The connection becomes starker when thinking through the translation of Ichabod’s story to the present. Do parents subtly imply, or even say outright, that what their child is learning holds little importance for their future? Do restrictions on class readings get handed down by administrators because a parent voiced concern that stories like Macbeth contain witchcraft? Do school stakeholders, to use a modern corporate term, shake their heads in disbelief that a teacher must work a second job to provide for their family? Or do they shrug their shoulders and comment that such is the price to enjoy an “easy” day job? 

Naturally, “The Legend of Sleepy Hollow” is not intended as a didactic tale with easy one-to-one correspondence for future application. And Ichabod Crane’s “easy life” is not meant as a model to be followed or avoided. Rather, it is a humorous caricature of the ways in which teachers and their communities view one another. But what surprises readers is just how much remains the same in spirit, even though the details may change. For many teachers, Ichabod’s “easy life” sounds all too familiar, with side jobs and an ingratiating approach to school donors occupying much of their time outside the classroom. They, like Ichabod, often wonder if they could find success in a different field, where they could deploy the same skills while earning a more reasonable living. In fact, the number of former classical teachers who leave the classroom to practice law or to become a small business owner might give the impression today that Irving’s writing was prophetic. 

The thing to note here is that Ichabod Crane’s community perceived him as a necessary but functionally worthless appendage to their little hamlet. A teacher who is perceived as valuing history and singing over the more practical matters of managing an estate or building a business, as though these are mutually exclusive endeavors, will be met with derision at every turn. And I would wager that no amount of emphasizing recruitment and retention will overcome such a communal context. The lessons of Ichabod Crane’s story revolve around things heavier than recruiting practices and clearly written onboarding practices. While such modern administrative practices might prove helpful at times, a school with the very best human resources department will still struggle to staff their classrooms if the community in and around the school behaves like Sleepy Hollow. If schools want to bring in quality teachers and keep them, then finding a way to cultivate a community of mutual trust and respect will be the most effective path forward. If they can manage that, then I imagine the salary problem will solve itself.