The Pizza Principal: A Guide to Accidental Success and Fulfillment

Photo by Austin Chan on Unsplash

Midway upon the journey of our life, I found myself within a forest dark, for the straightforward pathway had been lost.

Dante's words feel like they were written for moments of self-reflection—those times when we pause and look back, wondering how we ended up where we are. For me, the path has been anything but straightforward.

I wasn't just a bad student—I was a legendarily bad one. I still hold the all-time suspension record at my junior high (a record that will never be broken because the school eventually closed down). I was thrown out of my first high school, stayed back in 10th grade, and went to summer school every year from 8th grade through 11th grade—always for math. I graduated 197th out of 210 in my class, likely with more detentions and suspensions than all my classmates combined.

If you had told any of my teachers at Pilgrim High School that, of all things, I would be celebrating 25 years as an assistant principal next month, they would have laughed. Honestly, so would I. But life, as I've learned, is full of unanticipated surprises and opportunities.

It's not about where you start. It's about where you end up.

After high school, I started my post-secondary journey at CCRI because there were no other options. But that fresh start gave me the opportunity to transfer to Northeastern University, where I graduated with high honors. I went on to earn a Master's degree from there as well, working as a graduate assistant, and after beginning a career teaching and becoming an administrator, eventually completed all of the coursework for a doctorate in Educational Leadership at Johnson & Wales University.

For someone who once seemed destined to fail out of school entirely, the 52 consecutive years that I have spent in schools feels almost absurd. And yet, this has been my path.

Honestly, I never expected that writing—something I've done quietly and sometimes under a pseudonym—would bring me some of the opportunities I've had in my life.

In college, I wrote one-act plays and short stories in creative writing classes. One piece, about traveling back to school on the train after my grandmother's funeral and reflecting on the complicated relationships I had with some of those who paid their respects—and those who didn't—left an indelible mark on me. When I read it aloud, the room fell absolutely silent, broken only by the sound of quiet sobs scattered throughout. It was the first time I realized I could connect with people emotionally through my words.

Our visiting professor, a renowned playwright, pulled me aside after class. We had one of those heart-to-heart talks, where he urged me to take my writing further. The kind of talks that in the movies come right before the montage—you know the one: the aspiring writer furiously scribbling in notebooks, crumpling papers and throwing them across the room in frustration, reading to test audiences and watching their faces light up, all set to inspirational music. Rocky with a pen and loose-leaf paper.

In the movie version, this would be the turning point where everything changes.

It didn't—not then.

For years, I carried that "what if?" with me, wondering what might have happened if I'd pursued writing as a career. I explored writing quietly, almost in the background of my life.

Then something unexpected happened. When Rhode Island Food Fights announced their "Lord of the Pies" event, I took on what seemed like an impossible challenge: 35 pizzerias in 29 days. Each visit became a story, each pizza a character in a larger narrative. What started as simple reviews quickly turned into something more. A pizzeria owner, moved by my style of writing, asked if I would write his eulogy one day. Another reader declared they'd try a pizza made of dirt if I wrote about it. The response was immediate and electric - pizza fans in the forum weren't just reading, they were sharing their own stories, their memories, their recommendations.

The irony isn't lost on me that I've become known for food writing all of a sudden. I'm a notoriously picky eater—the kind who can count their acceptable foods on two hands with fingers to spare. My friends have turned my limited palate into a running joke, complete with a greatest hits list of my food phobias. And yet here I am, writing about pizza with enough passion and insight that people are showing up to restaurants because of my words.

Maybe it makes perfect sense: when you only eat about twelve things your whole life, you become something of an expert on those twelve things. Pizza just happens to be the one I love enough to write about. And when I say love, I mean I could legitimately eat pizza for lunch and dinner every day for the rest of my life and never get tired of it. It's probably an obsession at this point.

During Tumblr's heyday, I wrote under a pseudonym and built an audience of over 25,000 followers. But even then, I never imagined that writing—about food, of all things—would lead to the kinds of opportunities I've had recently.

Almost weekly, someone reaches out—drawn in by my writing. A local television producer working on developing a new show asked if I'd like to partner as a writer. A documentary filmmaker invited me to appear in a project about interesting or unusual people from Rhode Island after hearing his wife doing dramatic readings of my pizza reviews on the couch. And a business I've appreciated and admired for years is excited about finding ways for me to contribute my writing across different media and formats.

These opportunities aren't just humbling; they're exciting. They've given me a new sense of purpose and possibility.

But the journey hasn't been without its challenges.

On social media, my reviews and posts don't always get the likes or comments I might hope for, especially from people at work. That makes the ugly voices in my head whisper: They don't like it. They don't like you. They think what you're doing is weird. They think you're weird. You're talking like your Shakespeare but you're writing Pizza reviews, dude.

But then I step away from the screen and into real conversations with my colleagues during the day, and everything shifts. The same people who don't engage online are often the first to bring up my writing in person. They tell me how good it is, they ask where they need to go for pizza next, what inspired a particular review, or if I've checked out a spot yet that they love. Time and again, they tell me I'm spot on and they love the delivery (no pun intended). Pizzeria owners tell me customers are showing up excited to be there because of what I've written.

This dichotomy—between the public silence and private acknowledgment—has taught me something important: the work we do doesn't always need public validation to matter. The value of what I create isn't measured in likes or comments. It's measured in the human connections it fosters, the meaningful conversations it sparks, and the ways it inspires others to act.

That newfound realization has been transformative.

For years, self-consciousness and introversion held me back. But now, those parts of me are burning off like a spaceship re-entering Earth's atmosphere. The process is thrilling, disorienting, and undeniably life-changing. I'm meeting new, creative, interesting people who see something in me that I'm still learning to see in myself.

It feels like something significant is just beyond my reach. For now, I'm embracing every opportunity the universe provides, exploring who I want to work with and what I want to work on and trusting that I'll figure it out in time. I'm not in a rush. And in the process, I'm discovering something remarkable: I like who I'm becoming.

I'm comfortable in my skin in a way I never was before. I don't care if everyone likes what I do or even likes me. Because I do. And for the first time I can remember, that's enough.