If you’ve been reading these essays for a while, you already know that while some of my inspiration comes from the theologians and biblical commentaries, for better or for worse, a fair amount of it comes from 1980s rock and roll. This is probably not what my seminary professors had in mind when they spoke about the communion of saints, but I am quite certain God is considerably less fussy about His messengers than we are. Every now and then the prophets sound suspiciously like Bruce Springsteen, David Bowie, or Tom Petty. Every once in a while, they sound like Cyndi Lauper.

To a little girl growing up in Alexandria, Virginia, Cyndi Lauper was unlike anyone I had ever seen. The men of rock music had long been granted permission to be eccentric. Bob Dylan could scratch and mumble his way through a song. Heavy metal had practically abandoned melody altogether. Women, however, were expected to be beautiful and polished. Then Cyndi Lauper arrived looking as though she had wandered off a battlefield, her opponents a herd of wild peacocks. Her voice was scratchy and nasal and gloriously unconcerned with what anyone thought a female singer ought to sound like. She looked ridiculous and magnificent.

One of Cyndi’s earliest hits, Money Changes Everything, is about the way money quietly alters human relationships. Marriages. Friendships. Churches. Politics. As odd as it sounds, I find myself thinking about that refrain whenever I find myself wrestling with the complicated relationship between money and culture. More often than not, education enters the conversation before long.

For years, one of my favorite days on the school calendar was the annual middle school concert. Most schools have spring concerts where well-dressed children and their parents file into proper performance spaces to hear violin concertos. Our school had rock bands in parking lots. Every middle school student was required to join one. They spent weeks in rehearsal rooms learning songs. The point was never really musical excellence. The art of teaching twelve-year-olds consists largely of convincing them to risk looking foolish long enough to discover they are capable of becoming…rock stars.

One particular evening, as parents began arriving, one of the sixth-grade boys came running across the parking lot toward me. He was almost unrecognizable. Black eyeliner framed his eyes. Sweatbands wrapped his wrists. His ripped jeans and rolled T-shirt sleeves landed somewhere between an eighties rocker and a fifties greaser. Clutched tightly in his hand was a single feather earring inspired by Mr. T.

“Can you help me?” he asked. The tape holding the earring had given way.

So there I stood, head of school, carefully taping a feather to the ear of a sixth-grade boy while his impeccably dressed, perfectly composed mother looked on with the expression of someone quietly reevaluating our school’s educational philosophy.

The boys took the stage to thunderous applause. And it started: AC/DC’s You Shook Me All Night Long. About halfway through the first verse I experienced what I can only describe as a professional existential crisis. It suddenly occurred to me that these were, in fact, sixth graders enthusiastically singing one of the more spectacularly inappropriate songs in the history of rock music. I briefly considered whether I ought to intervene before parents made a beeline to clean out their children’s lockers and leave our little school once and for all.

Then I looked away from the stage and toward the audience. Not one parent appeared scandalized. They were laughing—not in that polite way people laugh when they are uncomfortable, but with the sort of delighted surprise that catches you completely off guard. They were singing along. Somewhere between the opening guitar riff and the final chorus, a parking lot full of responsible adults had become sixteen-year-old groupies.

It remains one of my favorite memories from those years at school, not because the boys were particularly gifted musicians—although they were remarkably good for a semester of guitar and drum lessons—but because something happened that evening that could never appear in an annual report or a college matriculation list. Those awkward little boys stopped worrying about whether they looked ridiculous. For three and a half minutes they became utterly fearless, and their parents had the extraordinary privilege of watching it happen.

If I had walked through that parking lot afterward and asked those mothers and fathers what they should have paid for those three and a half minutes, every one of them would have handed me a blank check. But the beautiful truth is that no amount of money could ever have purchased what they had just experienced.

I have thought about that evening many times over the years, particularly as tuition has continued its relentless climb and conversations about education have become increasingly dominated by economics. Parents naturally ask whether the investment is worth it. Rankings, amenities, placement statistics, and starting salaries have become the common currency by which we compare schools. None of this is irrational. If a family is spending tens of thousands of dollars each year on an education, it is perfectly reasonable to ask what they are receiving in return. The difficulty is that education has always been remarkably bad at measuring the very things it does best.

No annual report has ever listed “courage” among its outcomes on the “impact” report. Schools cannot quantify intellectual curiosity, resilience, moral imagination, or the confidence of a painfully awkward sixth grader who suddenly discovers he can stand in front of hundreds of people without fear. The finest schools certainly teach mathematics, history, chemistry, and languages, but they have always been engaged in another kind of work as well. Quietly, almost imperceptibly, they are forming human beings.

That, it seems to me, is where Cyndi Lauper’s refrain becomes unexpectedly helpful. Money changes everything. It builds classrooms, pays teachers, funds scholarships, and keeps the lights on. It can create the conditions in which education flourishes. It simply cannot buy the things that matter most.

All of this hinges on something that feels increasingly fragile in our culture. Teaching, while certainly an act of service, is not part of the service industry. The finest teachers I have known were never trying to entertain me. They were trying to make me wiser, often assigning books I did not want to read and asking questions I could not answer. They dismantled opinions I held with considerable confidence and replaced them with better questions. At the time, I often found the experience frustrating. Looking back, I realize the frustration was often the point. Growth has always required a certain amount of discomfort, and real wisdom has never been acquired through “customer satisfaction.”

It was only later, after years of leading schools, that I began to appreciate how easily market forces can reshape the language of education. I remember sitting with a veteran head of school in Los Angeles whose school never seemed to worry about enrollment because there was always a waiting list. As we talked about tuition, he smiled and offered what remains one of the most cynical—and honest—observations I have ever heard.

“You charge as much as the market will bear,” he said, “without making people think you’re in financial trouble.” I laughed at the time because I assumed he was exaggerating. Over the years, however, I have come to realize he was simply describing the world schools now inhabit.

Lest I sound as though I have climbed too far onto my educational soapbox, let me be clear: this is not an argument against the marketplace. Every school lives in one, and schools that refuse to engage it often discover that wonderful missions are no substitute for enrollment. The challenge is not whether to tell your story, but how.

A 2024 Wall Street Journal article, “Sorry, Harvard. Everyone Wants to Go to College in the South Now,” describes the remarkable growth of many Southern public universities, driven in part by the way they present campus life through social media. Prospective students are no longer simply reading admissions brochures; they are imagining themselves belonging to a community. Watch the social media accounts of Tennessee, Alabama, or Ole Miss and you will notice that they spend remarkably little time talking about faculty credentials. They tell stories. Football Saturdays. Residence hall friendships. Traditions. Professors laughing with students. They are selling culture.

There is nothing inherently wrong with that. In fact, many smaller schools could learn from it. Culture is one of the hardest things for an institution to explain, and social media has become an extraordinarily effective way to communicate what life actually feels like on a campus. The marketplace is not the enemy. The danger comes only when the marketplace begins shaping the identity of the school instead of simply helping the school tell its story.

One of the culture decisions we made at our school was that the custodial staff would do almost all of its work after students had gone home. Anyone who has spent five minutes around middle school students knows they possess an astonishing ability to leave behind backpacks, jackets, water bottles, lunch trays, science projects, and food wrappers. For the record, I love middle schoolers but they can be pretty disgusting. High schoolers are not much better. Every evening our custodians performed small miracles. During the day, however, students cleaned up after themselves.

I never wanted a twelve-year-old to develop the quiet assumption that someone else’s job was to follow behind cleaning up the consequences of his life. If a table needed wiping, students wiped it. If papers were left scattered across the classroom floor, they picked them up. Those were never housekeeping lessons. They were lessons in belonging, teaching that a community flourishes only when its members assume responsibility for one another.

We rarely know which moments in a school’s life are shaping character and which are simply passing time. The truth is that they are often the same moments. The small disciplines of ordinary days become the instincts we rely upon when extraordinary days arrive. Communities do not suddenly discover who they are in a crisis; they reveal who they have been becoming all along.

Years ago, the Archbishop of Canterbury, Rowan Williams recounted what happened at Trinity Church on September 11, when the towers fell just blocks away. As chaos spread through lower Manhattan, he and members of the staff helped carry children from the church’s preschool through the dust and debris to safety. Every head of school knows that nightmare—the day you pray never comes, when emergency plans suddenly become real and the only thing that matters is getting children home safely.

There is no salary large enough to purchase that kind of courage. No tuition high enough to guarantee those instincts. They grow out of something much deeper than a contractual relationship between employee and employer. They grow out of vocation, love, and the extraordinary bonds that healthy institutions cultivate over years.

Cyndi Lauper was right. Money changes everything. It builds classrooms, pays teachers, funds scholarships, equips laboratories, and keeps the lights on. Every good school depends upon it, and every educator knows the frustration of trying to accomplish great things without enough of it. This is not an argument against money. It is an argument against asking money to do what it cannot.

Money can create the conditions in which education flourishes, but it cannot manufacture education itself. It cannot purchase wisdom, courage, friendship, integrity, curiosity, or love. It cannot produce the unforgettable sight of a frightened sixth-grade boy discovering, beneath a stage light and wearing a feather earring held on with masking tape, that he is capable of becoming someone braver than he imagined. And it cannot pay someone enough to put their life on the line to save a child.

Those things belong to another economy altogether.

Preface to the series

For more than a decade, I had the extraordinary privilege of founding and serving as the first head of school of The Episcopal School of Los Angeles. People often ask me what it was like, and I usually find myself strangely at a loss for words. There are professions that can be described, and then there are professions that simply have to be lived. School leadership is equal parts educator, pastor, fundraiser, referee, counselor, diplomat, chief weather forecaster, and occasional magician. For me, it was also a time as a head chef, chief contractor and manager of every size Allen wrench capable of building or repairing furniture. It was also one of the greatest joys I have ever known.

Leaving was far more difficult than I expected. There were obvious reasons, of course, but what surprised me most was the profound loneliness that followed. I carried with me years of experiences that seemed impossible to explain to anyone who had not sat in that particular chair. There were moments that had given me life and moments that had broken my heart, conversations that still echoed in my memory, decisions that had kept me awake at night, and small acts of grace that I knew I would remember for the rest of my life. I assumed those memories belonged almost exclusively to me. What I have discovered over the years is that I was wrong.

After a year of keeping to myself, I began meeting other heads of school for lunch, for coffee, or simply for long conversations over the telephone. What I expected to be pleasant professional exchanges quickly became something much richer. Before long we were finishing one another’s stories. The impossible parent conference. The teacher whose quiet faithfulness held an entire community together. The board meeting that took an unexpected turn. The student who changed everyone’s lives. The impossible email that somehow arrived at exactly the wrong moment. Time after time I found myself laughing as someone described an experience I had privately assumed only I had lived.

It turns out that schools produce remarkably similar stories because they ask remarkably similar things of the people who lead them. Every head of school eventually discovers that the work requires equal measures of courage, humility, patience, imagination, endurance, forgiveness of self and others, AND a sense of humor. Without the last of those, I’m not entirely convinced the others are enough. This series grows out of those conversations.

If you are looking for stories that settle old scores or expose old wounds, I am afraid you will be deeply disappointed. I have neither the desire nor the temperament to air anyone’s laundry, and the older I become, the less interested I am in assigning villains to stories that usually involve well-intentioned people doing their imperfect best. Schools are wonderfully complicated communities. They are filled with teachers who arrive before sunrise, coaches who stay long after dark, administrators quietly solving problems no one else ever sees, trustees trying to steward institutions they love, parents doing the very difficult work of raising children, and students who somehow manage to surprise all of us every single day. My affection for that world remains far greater than any disappointment I may have carried away from it. In truth, I would much rather make you laugh and remind you of just how hopeful schools can be.

As another school year begins, I thought it might be good to pull back the curtain just a bit and share some of the things that people who spend their lives in schools often think but rarely say aloud. My hope is not to reveal secrets but to offer perspective. Parents spend thousands of hours trying to understand the children they love most. Those of us who have worked in schools spend thousands of hours trying to love those same children alongside them. We do not always see things in exactly the same way, but more often than not, we are working toward precisely the same end.

There is another reason these essays feel timely. I have been immersed in writing a memoir about my own school days, and revisiting that landscape has reminded me just how profoundly schools shape us. They become the settings for our first triumphs and failures, our deepest friendships, our earliest heartbreaks, and many of the people who quietly change the course of our lives. Writing these essays feels, in many ways, like returning to familiar ground.

If you happen to be a head of school—or any sort of leader—I hope you will find your own stories somewhere in these pages. Leadership has a curious way of convincing us that our burdens are uniquely our own, when in fact they are often widely shared. I have become convinced that leaders need one another more than we are inclined to admit, and I am always happy to serve as a sounding board, a fellow traveler, or simply a sympathetic ear.

Most of all, I hope these essays communicate the affection I continue to feel for schools and for the extraordinary people who fill them with life. They are, for all their imperfections, among the clearest expressions of love I know. Every lesson prepared, every rehearsal attended, every game coached, every difficult conversation, every encouraging word, every late evening and early morning is, at its heart, an act of hope offered on behalf of a child.

Those children, and the parents who love them, deserve our very best. These essays are offered in that same spirit.

Finally, I should acknowledge one other influence before we begin. I am an Episcopal priest, and my understanding of schools has always been shaped by that vocation. One of the gifts of the Episcopal tradition is that it has taught me to hold deep convictions while remaining genuinely curious about the convictions of others. Some of my favorite families over the years were deeply committed Jews, Muslims, Christians, agnostics, and people who were still sorting out what they believed. The finest Episcopal schools I know have never confused formation with indoctrination. They are unapologetically rooted in their own tradition while warmly welcoming people from every background, trusting that honest encounter with one another enlarges us all. My faith will undoubtedly find its way into these essays, not because I hope to persuade anyone to believe as I do, but because it has shaped the way I understand children, community, and the extraordinary privilege of helping young people become fully themselves.

Reflection 1: Fear

The single most important thing I ever learned as a head of school was this: parents operate out of fear. I do not mean that as a criticism. Quite the opposite. It is simply one of the great realities of raising children. Before a parent ever walks through the front doors of a school, they arrive carrying a thousand hopes for the person they love most in the world. Will my child make friends? Will she be kind? Will he be included? Will she discover what she loves? Will he be successful? Will my child be safe? The questions change with age, but the anxiety rarely disappears. In fact, I have often thought that one of the cruel ironies of parenting is that the more deeply you love your children, the more opportunities life gives you to be afraid for them.

Once I understood that fear, not as an occasional emotion but as the atmosphere in which so many parents make decisions, I became a much better head of school. Every difficult email sounded different. Every pointed question took on a different meaning. Every complaint, every suggestion, every expression of gratitude, every awkward conversation began to make more sense. If I forgot that fear was often sitting in the chair beside the parent, I was likely to misunderstand them. Worse still, I was likely to take their words personally.

The more difficult lesson came later– parents rarely recognize the degree to which their own fears shape the lives of their children and, by extension, the health of the entire school community. Fear has a way of disguising itself as advocacy, vigilance, certainty, or simply “being a good parent.” Sometimes it is all of those things. Sometimes it is something else entirely. Left unchecked, fear has an extraordinary ability to spread. Children absorb it. Other parents absorb it. Teachers begin responding to it. Before long, an entire community can find itself reacting to anxieties that were never named, only transmitted.

Not to sound like a goofy preacher but quite seriously if there is one thing I know: schools flourish when love is stronger than fear. They struggle and even fail whenever fear begins making the decisions. That may sound like a harsh way to begin a series about schools. I don’t mean it that way. Understanding fear is one of the deepest acts of compassion a school leader can offer parents. Understanding our own fears may be one of the greatest gifts parents can offer their children.

Nearly thirty years ago, sociologist Sharon Hays put language to something many parents were already beginning to experience. In The Cultural Contradictions of Motherhood, she described what she called the ideology of “intensive mothering”—the growing expectation that good parents should devote extraordinary amounts of time, emotional energy, attention, and financial resources to optimizing every aspect of a child’s life. Although Hays was writing primarily about mothers, the culture she described has long since become the air that all parents breathe. Raising children has increasingly become an exercise in managing risk, anticipating every possible obstacle, and quietly believing that the next decision may determine the rest of a child’s life. It is an exhausting way to parent because it leaves very little room for ordinary childhood, ordinary mistakes, or ordinary trust.

What fascinates me is that many of the people now leading schools were themselves raised in a very different world. We were not abandoned to the wilderness, raised by wild dogs as we like to sometimes suggest, we simply had parents who occupied a little less space in our daily lives. We rode our bikes until dark, settled playground disagreements with varying degrees of success, forgot our lunches often enough to become resourceful, and generally assumed that if we got ourselves into a manageable amount of trouble, we would also have to figure out how to get ourselves out of it. There were certainly disadvantages to that kind of childhood, and I have no interest in romanticizing it. But it also produced adults who were accustomed to solving problems without assuming that every setback would permanently alter the course of our lives.

That difference in perspective matters more than most people realize. Parents today have been taught by experts, by social media, by college admissions culture, and by the sheer volume of information available, that the little things carry enormous consequences. From the head of school’s chair, however, I learned that the little things are almost never the issue themselves. They become stand-ins for much larger fears. A friendship gone sideways is no longer simply a friendship gone sideways; it becomes a question about belonging. A disappointing grade is no longer about one test; it becomes a question about the future. The event may be small. The fear it awakens almost never is.

How this all works in practice…

One of the pieces of advice I tried to offer parents at the beginning of every school year had very little to do with homework, backpacks, or college admissions. It was simply this: if your child comes home convinced that something terrible happened in math class that morning, resist the urge to write to the teacher before you go to bed.

Perhaps this may seem obvious but in general, when something happens in a classroom at ten o’clock in the morning—particularly if it involves embarrassment, disappointment, conflict, or shame—it rarely remains the same size by six o’clock that evening. Children replay the event in their minds. They think about what they should have said. They imagine what everyone else must have been thinking. They tell a friend. They relive it on the bus ride home. By the time they arrive at the dinner table, the story has often become something rather different from the event itself.

I have always thought of it as the Jaws phenomenon. At ten o’clock, the incident may have been nothing more than a perfectly respectable four-foot sand shark. By bedtime, after eight hours of anxious reflection and imaginative editing, it has become a fifteen-foot great white complete with its own John Williams soundtrack. Steven Spielberg himself would have looked at it and thought, “Now there’s a shark.”

Children are not lying when this happens. They are simply doing what all human beings do. Anxiety has an extraordinary ability to enlarge memory. Adults are no different. We simply become more articulate storytellers.

The difficulty, of course, is that parents hear the story only after this transformation has taken place. You are not responding to what happened at ten o’clock that morning. You are responding to what happened after it has spent the better part of a day marinating in disappointment, fear, embarrassment, and imagination. Before long, your own imagination joins the story. A disappointing quiz becomes a failing math class. A difficult conversation with a teacher becomes evidence that your child is misunderstood. One awkward afternoon begins to feel suspiciously like a pattern. By eleven o’clock that evening, many otherwise thoughtful, generous, and perfectly rational adults have composed what can only be described as a doctoral dissertation questioning not only the teacher’s command of mathematics, but the judgment of the department chair who hired her, the discernment of the head of school who retained her, the wisdom of the Board of Trustees who oversee the institution, and, before the final paragraph mercifully concludes, the future of Western civilization if this sort of thing is allowed to continue in eighth-grade Algebra.

If I may, permit me to let you in on a small secret? At least in my own former school and experience, teachers were generally encouraged to share difficult parent correspondence with the division head or the head of school. Not because we enjoy reading midnight manifestos over our morning coffee, but because teachers deserve support and perspective just as parents do. Which means there is a very good chance that before your child’s math teacher has even finished her first cup of coffee, I have also become acquainted with your assessment of her professional competence, her moral character, and, occasionally, her apparent inability to distinguish between the curriculum standards and the collapse of civilization.

Then something rather predictable happens. You come into the school office. The teacher comes in. Then everyone begins reconstructing what actually occurred in the classroom at approximately 10:15 on Tuesday morning. Your child remembers a few additional details. The teacher remembers a few that never made it home. Everyone discovers that there were thirteen other children in the room, all of whom somehow survived the experience. Gradually, almost imperceptibly, the fifteen-foot great white begins shrinking back into the perfectly respectable little sand shark it always was. It is usually about this point that someone says, with admirable honesty, “I may have overreacted.”

The truth is that I have enormous sympathy for parents in these moments because I know exactly what it feels like to become convinced that one absolutely must write the letter.

At different points in our lives and careers, my father and I have each sought the counsel of one of our favorite monks at a monastery in Cambridge, Massachusetts, about a similar predicament. Each of us, at one time or another, had written a letter that felt entirely justified and, in our own estimation, destined to set the world aright. Mine, at least, was eloquent, devastating, and left absolutely no room for misunderstanding. In other words, it was exactly the sort of letter one should never send.

When I talked to the monk about my own need to “get everything on the table” he listened with great patience. When I had finally exhausted myself, he smiled and offered a single sentence of advice.

“Write it,” he said. “Then give it to God.”

At the time I found this deeply unsatisfying. I was hoping for vindication. What I was given was wisdom (alas). Over the years, I have come to appreciate the distinction. There is tremendous value in writing the letter. Say everything that needs to be said. Spare no adjective. Construct your case with all the brilliance your indignation can muster. Let it breathe with the fire of a thousand dragons in flight. I have written a great many such letters over the years. Some have been eloquent. Some have bordered on the theatrical. I imagine Our Lord has occasionally smiled while reading them. Very few have ever needed a stamp.

There is something profoundly clarifying about allowing frustration to exhaust itself on paper. By morning, the emotional temperature has almost always fallen. The villain has become another human being. The catastrophe has become a problem to solve. Perspective is like good wine: it rarely improves with ice, and it rarely arrives before midnight… It usually wanders in sometime around breakfast.

So here is my advice. If your child comes home convinced that the math teacher has ruined their academic future, write the email if you must. Get every glorious word onto the page. Compare the quiz to the fall of Rome if it helps. Question the teacher’s methods, the school’s philosophy, and the future of civilization.

Then do one more thing. Give it to God. Go to bed. The math teacher almost certainly already has. If, by morning, you still believe every word you wrote, then send it. But after twenty-five years of working with parents and students, I can assure you that daylight has rescued more relationships between parents and teachers than any head of school ever could.

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