One of my best friends retired at the end of the school year.
We taught together for almost thirty years in the same social studies department. I will miss his big personality (and inappropriate jokes) at staff meetings. My faculty mailbox will be noticeably emptier now that we can no longer dump unwanted trash into each other’s boxes as an ongoing joke. I will even miss our bickering about current events. Over the years our political views have diverged, especially since the rise of the MAGA movement, but we never ceased to be genuine friends.
As the years have passed, I have watched close friends retire, transfer to other campuses, and, in one heartbreaking case, pass away from cancer. I teach at the same high school I attended as a student. For many years, I watched my favorite teachers leave the profession. But this retirement has hit me hard.
My friend was the longest-serving member of the faculty. He was the “old man” on campus. His retirement has now left a vacancy for the “old man” moniker, one I seem fated to inherit in just a few years as I am now tied for the second-longest-serving teacher on campus.
Soon, I will be standing on top of this disquieting mountain.
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Sign up and get our daily essays sent straight to your inbox.I always knew this day would come, and I’m not sure it’s a good thing. Veteran teachers who enter their fifties, as I have just done this summer, tend to follow one of two paths when reaching the sunset of their careers: either they acquire a quiet authority that makes them beloved institutional figures, or they become so cynical and crotchety that they gradually marginalize themselves in the eyes of colleagues. Sometimes their toxicity is so potent that everyone starts to think the same thing: it’s time for you to retire.
I have spent this summer reflecting on how best to avoid this fate.
Since this is not only the summer of my fiftieth birthday, but also the summer of The Odyssey, it is timely and helpful to realize that teachers who reach their fifties often begin to hear the song of the pedagogic Sirens. In The Odyssey they call out to Odysseus, singing:
Never has any sailor passed our shores in his black craft
until he has heard the honeyed voices pouring from our lips …
But in the classroom, what these “honeyed voices” offer veteran teachers is a personification of accumulated wisdom from throughout their careers. Their song is seductive because it sounds remarkably like the accumulated wisdom of long experience, crying out to veteran teachers standing wearily in the stern of their teaching ships. If heeded to excess, this old man wisdom can slowly curdle into cynicism and snark, then self-indulgent crankiness, and finally, a kind of professional early death from alienation.
As the Greeks knew well, knowing too much can often stifle more than stimulate, deaden more than enliven. The Sirens of experience tempt veteran teachers with a dangerous promise: that nothing in education can surprise them. Every new initiative is a signpost of decline. New teachers never have anything to offer. The teacher version of Siren song sounds like a melody of erudition. But sadly, it is often cynicism wearing the mask of experience.
We teachers in our fifties are a skeptical lot—and for good reason. Three decades on a campus gives you a trustworthy intuition for which policies are worth trying and which are predictable disasters. But that same experience has also taught me to change my mind.
In the first decade of my career, during the era of No Child Left Behind, I bemoaned the obsession with standardized testing and data-driven instruction. I was certain it would drain the joy out of the classroom and let bad teachers hide behind “teaching to the test.”
The reality was different. I came to see that inspiration alone isn’t enough—effective teaching needs clear objectives too. What do students need to know? What should they be able to do on the last day of school that they couldn’t do on the first? Test scores gave us a way to answer those questions and gave us something I hadn’t expected: camaraderie. We were united in our desire to beat the school across town. No one wanted to be the weak link.
I was just as skeptical of giving partial credit for missing work—it felt like rewarding students for doing nothing. But a zero does not just record a failure; it distorts the whole average, turning one missed assignment into the grade that defines the semester. If an A and an F should average a C, not an F, then partial credit is not leniency. It is arithmetic.
Sometimes, however, our skepticism is justified.
Recently, a school district in upstate New York launched a plan to use an AI humanoid robot in the classroom and quickly had to pause the plan due to overwhelming teacher and parent concerns. Earlier this year, First Lady Melania Trump walked into the White House East Room next to a robot. She asked the audience to
[i]magine a humanoid educator named “Plato.” Access to the classical studies is now instantaneous—literature, science, art, philosophy, mathematics, and history—Humanity’s entire corpus of information is available in the comfort of your home. Plato will provide a personalized experience, adaptive to the needs of each student. Plato is always patient, and always available.
But Plato wasn’t personal and patient; he was unnerving and dystopian.
There are certain universal and timeless truths about what works in a classroom that no technological advancement (even a humanoid robot) will ever change. And this knowledge is where being the old man on campus can have power and resonance.
The greatest source of classroom magic never emanates from the newest software or the most cutting-edge gizmos, but from the common humanity of teacher and student. It is rooted in the timeless relationship between the instructor and the learner—a relationship devoted to enlarging a young person’s intellectual and moral horizons in the hope of helping students live richer, more meaningful lives. The most powerful teaching tool in the world is communicating to a child that a teacher cares about his success—something no AI humanoid or Chromebook can ever do.
As I have grown older, I have found that communicating this simple truth has become more difficult. Sometimes my caring becomes twisted into frustration. I find myself, despite my best intentions, getting agitated, and I can hear the song of the Sirens. I don’t live online. I don’t know the endlessly evolving slang. I don’t think it’s unreasonable to ask my students to read difficult texts, study for an exam, or embrace a five-day school week. Their dizzying absenteeism remains a constant source of frustration.
The chasm separating a fifty-year-old man from a modern high school senior is sometimes so profound, so gaping, that we seem like different species. Just as I have trouble understanding them, I know they sometimes have trouble understanding me.
The distance between us widens as the years roll on. I age, while my students remain perpetually seventeen. I have lost both parents and my older sister. Some of my closest friends have endured colossal tragedies. How do I explain to teenagers the torment of lost pregnancies or the endless pressure of raising a family? How do I describe the torture of kidney stones or my private fear of suffering the indignities of old age?
Most of all, how can my students possibly understand that my greatest fear in the decade ahead has nothing to do with money, health, or marriage? I worry that this profession I have cherished my whole life—one that has shaped my soul and colored nearly all my dreams—will change so much that I can no longer do it. I fear that what I have to offer will be ignored, mocked, or deemed irrelevant.
More alarming still, what if the one gift I have always possessed in the classroom suddenly deserts me? I have always been able to communicate my passion for the American experiment in self-government: my reverence for the achievements won by generations of extraordinary men and women, and my gratitude for the sacrifices of countless citizens whose quiet labor made my freedom possible. What if, in the years ahead, that passion no longer reaches anyone? What if I become an out-of-touch, well-meaning old man who can no longer ignite even the smallest spark of civic curiosity or pride—an actor still delivering the same familiar lines after the audience has stopped finding the story compelling?
Earlier this year, one of America’s most beloved novelists, Pulitzer Prize winner Elizabeth Strout, published the novel The Things We Never Say, about an aging and once-great high school history teacher, Artie Dam, who begins to feel the creep of insignificance as he ages in the classroom. Strout’s description of Dam’s angst gives voice to what it means to fear becoming the Old Man on campus, what it means to fear the Sirens, and alas, what it means to fear the loss of being able to touch souls and ameliorate minds:
He was flooded with a great understanding. He was not fully himself any longer. He could not have described this to anyone, and he could not describe it to himself, but his mind seemed to be increasingly separated from this world: His mind was here, and the world was there. He was on a downward-sloping path, and no matter how hard he would try, he understood that day as he sat in his car that something was going to happen to him and he would not be able to prevent it.
I have no doubt that I will become the Old Man on campus. But which Old Man I become remains a mystery. I hope I can ignore the seduction of the Sirens. I hope I can avoid the fate of Artie Dam.
Above all, I hope I become a bridge that leads students to a lifetime of learning rather than a barrier that turns them away from the enchantments that can only be enjoyed by a truly educated mind.








