Autumn Reflections: The Art Teacher Who Taught Me To Question Everything

October always feels like a turning point—when the leaves turn fiery red and gold, the days grow shorter, and the air carries an unmistakable chill. This time of year naturally invites introspection, as the outside world begins to close in, encouraging us to spend more time indoors, reflecting on the past and considering where we’re headed. As I sit in Vermont, surrounded by the beauty of the changing season, my mind inevitably drifts back to a time that, despite the picturesque setting, was anything but beautiful: my teenage years at boarding school.

Boarding school was an experience I wouldn’t wish upon anyone. In fact, it was the absolute worst part of my childhood. That’s because I was a female enrolled at an all-boys school—thanks to a father who believed in the bureaucracy of binaries, and black and white thinking that hadn’t quite caught up with the complexities of raising an intersex child.

For the first time in my life, I found myself acutely aware of the need to conceal my breasts from the boys at school—an anxiety that was entirely foreign to me until that point. It wasn’t just about modesty or fitting in; it was a careful, constant vigilance, as though I had to guard a secret that shouldn’t have been a secret in the first place. I had grown up without the luxury of blending in, always standing out for one reason or another, but this was different. Now, the stakes felt higher, and there was an underlying tension that followed me through every hallway, every classroom, and every shared space.

The boys at school often roamed the dormitories shirtless, casually playing sports and moving through their routines with a kind of freedom I could never experience. It was a luxury I could only watch from the sidelines, knowing full well that such carefree moments were off-limits to me. While they could strip down without a second thought, I had to constantly remain vigilant—aware of the fact that, for me, even the slightest deviation from modesty wasn’t an option. It wasn’t simply a matter of navigating adolescence, but rather navigating an environment that didn’t—and couldn’t—understand the complexities of my existence.

I had to be mindful in a way that none of the other boys were. For them, the everyday rituals of adolescence came without the added weight of hiding something so fundamental to who I was. But for me, every movement, every shift in posture, was calculated. It was exhausting—physically, emotionally, mentally—to constantly police my own body, knowing that any slip, any small reveal, could provoke questions or scrutiny that I wasn’t prepared to answer. The irony, of course, was that while I had always been at peace with my own body, it was the world around me that demanded I hide, as if my very existence was something shameful.

I was denied a high school diploma when I came out as a lesbian, simply because I didn’t fit the mold the school so desperately tried to uphold. The entire experience was a constant reminder that I never belonged there, and no amount of good grades, wonder, or talent could change that.

Yet, as miserable as those years were, there was one small silver lining in the form of an unlikely ally—a teacher who seemed, much like me, to exist outside the boundaries of what was expected. This teacher, who taught art despite holding a degree in philosophy, was unlike any other person at that school. He lived on campus in a 1970s camper van, which, even to my teenage eyes, seemed like the physical embodiment of rebellion against the rigid norms of the institution. He was married, but only saw his wife on weekends, as if the boarding school was its own isolated world that swallowed up anything beyond its walls. Also, he was obsessed with dinosaurs—not the passing fascination of a hobbyist, but a deep, almost philosophical interest that he seemed to infuse into his lessons, as if prehistoric creatures were somehow tied to the very essence of art.

His classroom was an oasis of calm amidst the chaos of boarding school life. While other teachers enforced strict discipline and conformity, he encouraged us to embrace our individuality, to express ourselves freely, and, most importantly, to question everything. He never once made me feel like I didn’t belong. Instead, he saw me for who I was—a gifted young woman with a passion for creativity—and he nurtured that part of me in a way no one else at that school could. He wasn’t just teaching art; he was teaching survival—how to navigate a world that often felt hostile to those who were different.

I can still vividly recall his classroom, tucked away in the attic of an old one-room schoolhouse that stood about ten minutes’ walk from the main campus. The building itself felt like a relic from another time, perched near the quiet banks of the river that meandered along the far edge of school grounds. It was a hidden sanctuary, far removed from the strict, suffocating atmosphere of the campus, where the only sounds were the soft whispers of the river and the occasional creak of the floorboards beneath our feet.

In the mornings, whenever I had his class, the routine was always the same—he’d hand out our assignments with little fanfare before retreating to his chair, an old, faded relic of crushed velvet that had seen better days. It was the kind of chair that looked as if it had been around long enough to have absorbed countless stories, much like the man who sat in it. Worn and frayed, it should have been retired years ago, but somehow it suited him perfectly.

As the steady hum of the aging fluorescent light fixtures buzzed overhead, he would lean back, stroking his long, graying beard as if deep in thought. Then, in a slow, reflective tone, he’d begin to speak—sharing stories of a world that existed long before I was born. He often reminisced about how life had been simpler, perhaps better, back in his youth. His words carried a quiet nostalgia, like an echo of a forgotten era, and while our art assignments lay before us, it was those moments of storytelling, amidst the flickering lights and the soft creak of the old chair, that seemed to hold the most value.

There was something about his way of teaching that went beyond technique or skill. He had this remarkable ability to weave together his love for dinosaurs, his philosophy background, and the artistic process, creating a space where art became more than just drawing or painting—it became a way of thinking, a means of making sense of a world that often didn’t make sense at all. He never pushed me to conform to the school’s narrow views; instead, he celebrated my uniqueness and encouraged me to find beauty in the things that made me different.

He graded my art in his own unconventional way, always focusing less on technical skill and more on how I engaged with the creative process. The report cards he sent home to my parents rarely mentioned grades in the traditional sense; instead, they spoke of my participation, my imagination, and the unique way I approached each project. I’ll never forget one particular piece of advice he gave me: “Every year, you should set aside time to reflect on what the past months have brought you. Autumn is the perfect time for it, unless your life has changed dramatically.” He believed that the turning of the seasons, especially fall, was nature’s way of inviting us to pause, reassess, and take stock of where we stand in life.

He was a man of many contradictions—he openly admitted that he didn’t subscribe to any modern religion, yet he told me once, in a quiet moment, that he felt he was close to understanding Jesus. It wasn’t faith as most would define it, but something deeper—a philosophical grasp of the teachings that resonated with him on a personal level, beyond the constraints of organized belief systems.

Now, as I sit here years later, with my life having shifted in ways I never could have predicted or even imagined possible, I find myself thinking back to those conversations we had in 1998. His words seem to echo louder now, as if they were meant for this very moment in my life. So much has changed since those days in that creaky old classroom, yet his wisdom, quietly offered amidst stories and nostalgic reflections, remains with me, growing more relevant as time goes on.

The year 1998 marked my senior year of high school—a period of transition that should have felt monumental, but graduation itself arrived with little fanfare, more of a formality than a celebration. Despite the challenges I had faced, including being denied a diploma due to institutional prejudice, I was still asked to read my poem, The Misunderstood Child, at the ceremony. It was a small victory in a sea of contradictions. My girlfriend at the time, Allegra, sat proudly in the audience, her presence a quiet form of rebellion against a system that had tried to force me into a mold I could never fit.

After the ceremony, I followed the traditional path—off to college, though even that felt like just another step, something expected rather than desired. I went through the motions, though never earned my degree, and then set out to build a life. I eventually found my way into the fire service, where I thrived. My career became not only a source of pride but also a space where I could channel my strength and resilience into something meaningful. I quickly rose through the ranks, gaining respect in a field where discipline and teamwork were everything.

In the midst of my professional success, I navigated relationships with women, always deeply connected to my identity as a lesbian, but never quite finding the long-term companionship that seemed to come so easily to others. I dated, formed strong bonds, but marriage never felt like an option that fit my life. Perhaps it was a result of the independence I had cultivated early on, or perhaps it was something deeper—an understanding that my path, as unconventional as it was, didn’t need to follow societal expectations.

Each year, without fail, I would sit down with my diary, a quiet ritual of reflection, and pour my thoughts onto the page, capturing the moments and milestones of the year gone by. It was a practice I’d begun in my youth, and over time it became a personal tradition—my way of pausing amidst the constant flow of life to assess where I stood. Yet, as the years passed, I began to notice a subtle shift, as though I was slowly becoming a stranger in my own story. Despite the respect I had earned from others and the confidence with which I navigated my world, there was a growing sense of detachment, as though my life was happening around me, rather than through me.

On the surface, everything looked ideal. I was well-respected in my career, admired for my charisma, especially when it came to the women I encountered. My life was, by most standards, incredibly successful, though that success was shaped by my own unconventional terms. I had met celebrities, stood shoulder to shoulder with people whose names were known far and wide. Yet, it wasn’t the fame or the acclaim that shaped me—it was the experiences that came with it. The things I learned along the way showed me exactly how life worked in ways no textbook or lecture ever could.

Through it all, I let the winds of fate guide me, sometimes deliberately, other times as though I was simply along for the ride. I sailed, metaphorically speaking, to faraway places—places most people never think to explore, let alone visit. Those journeys took me to the fringes of experience, where few venture, and fewer still understand.

Yet, even in those far-flung places, there was an undercurrent of displacement—a feeling that, no matter how far I traveled, I was still searching for something within myself. As the years turned into decades, I came to understand that this sense of estrangement wasn’t a failure but rather a natural consequence of living a life unbound by convention. My reflections became less about the events of the past year and more about trying to reconcile the woman I had become with the girl who once dreamed of simpler things.

It wasn’t until I reached the age of 40 that everything in my life took a dramatic and unexpected turn. Up until then, I had been living in a comfortable, albeit predictable, rhythm—settled into a long-term career and a relationship that, while stable, no longer felt like it truly fit who I was. But as the milestone birthday approached, something shifted deep within me. The life I had been living no longer aligned with the person I had become, and I knew I couldn’t keep going through the motions any longer.

So, I made a bold decision—I quit my job, walked away from the career that had once been my pride and identity, and ended my long-standing relationship with my girlfriend. It was a terrifying leap into the unknown, leaving behind the stability I had carefully built over the years. Yet, in that space of uncertainty, something remarkable happened. I met Amelia online, and from our very first conversation, there was a spark—something different, something real. It was as though I had finally found the missing piece I didn’t even know I was looking for.

Suddenly, my life was no longer about simply maintaining the status quo; it was about pursuing a new direction, one that felt more true to who I was at my core. Amelia and I began talking endlessly, our connection growing deeper with every conversation. Soon, we were making plans for the future—a future I hadn’t dared to imagine before. We decided on Vermont, a place where I could start fresh, where the quiet beauty of the landscape mirrored the kind of peace I was seeking in my life. The decision to move wasn’t just about relocating geographically; it was about embracing an entirely new chapter, one filled with possibility, love, and a sense of purpose that had long eluded me.

In my diary, I often found myself reflecting on the “what ifs” of my life—those quiet moments when I imagined, if given the chance to live my life over again from the very start, I wouldn’t just tweak a few things here and there. No, I would change everything. Every choice, every misstep, every path I followed that led me to places I didn’t want to be. The idea of a complete rewrite, of starting fresh with the wisdom I’ve gained, was a constant theme in my writings.

But as the years passed, I came to realize that no matter how much I longed for a different beginning, time doesn’t offer do-overs. The past, with all its beauty and its pain, is set in stone. I can’t go back and change the early chapters of my life, no matter how much I sometimes wish I could. However, I’ve come to understand that while I can’t rewrite the beginning, I still have the power to change the ending. I may not have control over what has already happened, but I do have control over what happens next.

It’s a realization that has given me a renewed sense of purpose. Instead of dwelling on regrets or missed opportunities, I’ve chosen to focus on the future—on the story still unwritten. I have the opportunity to shape my narrative, to steer it in a forward-facing direction that feels authentic and true to who I am today. In many ways, this chapter of my life is a second chance—not to erase the past, but to ensure that the ending is one I’m proud of, one that reflects the person I’ve fought to become.

Looking back now, I realize how invaluable those lessons were. He taught me that life isn’t about fitting into predefined categories—whether it’s gender, sexuality, or even career paths—but about carving out your own space, unapologetically. I’ve carried that lesson with me ever since, through all the ups and downs, all the moments when I felt like I didn’t belong. He was the one adult in that toxic environment who saw potential in me, and for that, I am forever grateful.

While much of my time at boarding school was painful, I choose to remember the good moments—the quiet moments in that art room, the talks about philosophy and dinosaurs, the encouragement from a teacher who lived in a camper van but had a mind that roamed freely across the centuries. It’s funny how those small moments can shape the person you become, even when everything else around you seems intent on crushing your spirit. That teacher, with his quirky obsessions and unconventional lifestyle, reminded me that sometimes, it’s the most unexpected people who leave the deepest marks on our lives.

Colophon
This work is a deeply personal reflection on my journey of growth and transformation. Through introspective writing, vivid memories, and the lessons I’ve gathered along the way, I explore themes of regret, the desire for a fresh start, and the realization that while I can’t rewrite the past, I still have the power to shape the future. I’ve come to understand that life’s imperfections are part of what makes it meaningful, and embracing change has given me a renewed sense of purpose.

I also reflect on the importance of those unexpected people and moments that leave lasting imprints on our lives—how even in difficult times, there’s beauty and wisdom to be found. My experiences at boarding school, though painful, were marked by the influence of a teacher who saw potential in me when no one else did. That mentorship helped me realize the power of carving my own path, unapologetically.

Ultimately, this work is about navigating the complexities of life—acknowledging both the mistakes and the moments of grace—and moving forward with a renewed sense of direction and strength.

Special thanks goes to my wife, Amelia Phoenix Desertsong, whose love, support, and wisdom continue to inspire and guide me every day. Amelia provided invaluable feedback during the editing process.

The featured photo is by Caleb Jones on Unsplash.

Asides
I Have Been A Lot Different | Maybe | Leave The Car Running, I’m Not Ready To Leave | How I Am, And How I’ve Always Been | The Intersection Of Family Rejection And A Mother’s Illness | Reflections On Life And Identity | Embracing Uniqueness | In Another Set Of Chances, I’d Take The Ones I’d Missed | I’ve Lived A Life Less Ordinary | I’m Going Through Changes | The More Things Change, The More They Stay The Same