After 27 years of teaching, I find myself sitting at home today as my wife, Elysha, returns to school for her first day of work.
This is the first test of how I will feel about not teaching this year.
It’s admittedly an odd feeling. For most of my life, my days have been dictated by the school calendar.
From ages 5 through 18, my life was centered around elementary, middle, and high school. Vacations, holidays, and my day-to-day existence revolved around the heartbeat of school.
I graduated from high school in 1989 and struggled for six years before finally returning to school in the fall of 1994 at Manchester Community College. From 1994 through 1999, I attended and graduated from Manchester Community College, Trinity College, and St. Joseph’s University.
I also worked full-time as a McDonald’s manager and part-time at the school’s writing center, and my partner and I launched our wedding DJ company during that time, too, but I was a full-time student through it all.
Once again, my life was dictated by the rhythms of school.
Then, in 1999, I began my teaching career at Wolcott School. I taught at that school for 27 years, almost all of it in the same classroom, before retiring from the profession last year.
Aside from a six-year gap between high school and college, I have returned to school every September since I was five years old to begin class, either as a student or a teacher.
That schedule, rhythm, and pace are no longer a part of my life.
Today, I consult with corporate clients, filmmakers, entrepreneurs, YouTube creators, nonprofits, and more. I deliver keynotes around the world. Write books. Tell stories onstage. Produce shows.
At times, it’s a little like teaching, but it’s definitely not teaching.
Elysha went off to convocation this morning — an opening event that many of my colleagues do not enjoy and sometimes skip entirely — but one that I enjoyed immensely. It was an opportunity to listen to speakers attempt to inspire us about the coming year. It was a mix of educators, politicians, and professionals who often leaned into platitudes and banality but occasionally offered moments of true insight and inspiration.
I would begin every morning before convocation with a quick round of golf, often with a friend when they were available and sometimes on my own. I would walk a little executive course near the school as the sun rose, chasing a small, white ball and often seeing deer, coyotes, and a bobcat who liked to keep an eye on me.
Then, after sucking up the final marrow from my summer, I’d grab an Egg McMuffin and head over to the high school for convocation.
Walking through those doors always felt great. For the first time in two months, I saw many of my friends again.
Then it was into the auditorium for the program.
A student speaks every year, and this is always glorious. Three years ago, my former student, Shylo Peak, spoke, and for part of her speech, she essentially made fun of me in front of about one thousand of my colleagues.
I taught her well.
Back in 2005, when I was West Hartford’s Teacher of the Year, I had the opportunity to deliver a speech to my colleagues. At the time, it was one of the highlights of my career, and other than referring to my fellow Teacher of the Year finalists as “girls” — a verbal slip I still regret today — it went really well. I told a story that eventually became one I would tell on stages all over the world, after accidentally launching my storytelling career six years later by telling a story at The Moth.
That storytelling career eventually led to my retirement. What began as a whim — go to New York and tell a story for The Moth — now has me speaking to corporations around the world and consulting with everyone from Amazon to Microsoft to Yale University to the FBI.
Little do we know where doors will take us if we are willing to open them,
At convocation the following year, I had the chance to take the stage once again to introduce the next Teacher of the Year. I used the opportunity to speak briefly about my year serving as Teacher of the Year and being named one of three finalists for Connecticut’s Teacher of the Year. I spoke about the honor of representing our school district and the appreciation I felt for my colleagues.
I also took a shot at a small group of moronic administrators who had recently taken the keys from colleagues at certain schools, preventing access to their classrooms over the summer when they often get their classrooms ready.
Never miss an opportunity to let an administrator know how you feel about them publicly.
Over the years, other close friends have had the chance to speak at convocation as Teacher of the Year, including Wolcott School teachers Andy Mayo, Kathy Paquette, and Jennifer Stanish.
Those convocations were extra special.
My former principal, Plato Karafelis, introduced music to convocation during the year our school hosted the event, and ever since, convocation opens with a musical performance by a group of students.
Most folks have probably forgotten that Plato started that tradition.
Last year, my former colleague, friend, and storyteller Christina Fedolfi, our most recent Teacher of the Year, spoke. She was infectiously enthusiastic and hilarious.
It was my last convocation, and I’m so happy she was my final speaker.
We also had inspirational speakers at convocation over the years — administrators and hired speakers who took the stage to make our hearts soar. Some were excellent, including our former superintendent, Tom Moore, who never hired speakers, never stared at notes, but did the job himself.
Brilliantly so.
Some of those hired speakers — men and women doing the kind of work I do today — were excellent, too.
A principal in our district once spoke about how his immigrant mother made sure he had the right lunchbox every year, recognizing it as social capital and a way to feel part of the culture. He placed one of those lunchboxes on a stool as he spoke, and he brought tears to my eyes. He reminded us that behind every student is a parent and all of their hopes and dreams for their child.
I’ll never forget that speech.
We also had speakers offer nonsense over the years, including one who used a crown as a metaphor for achievement—one that the district administration sadly latched onto for the next two years. It was a ridiculous, logically inconsistent, tone-deaf, and socioeconomically blind idea that needed to go away.
Thankfully, it eventually did.
Good and bad, brilliant and banal. I loved convocation and always thought that the teachers who despised it or skipped it entirely were foolish. Ceremony, tradition, and rhythm are what mark a school year. It begins with a gathering of people who love children choosing to occupy the same space for a short period of time to say hello, catch up on what had transpired over the summer, and align themselves to the work at hand.
I loved it.
Then I loved arriving at school around 11:00 AM after playing the par 3 adjacent to the high school a couple of times between foursomes — one final squeezing of the marrow from summer. I would unlock my classroom door for the first time since the middle of June, and less than an hour later, I’d be ready for the school year.
After 27 years of teaching, including a quarter century in the same classroom, and possessing a minimalist spirit, it took me less than an hour to get ready every year.
It drove my colleague, Kerry Lynn, crazy, which was also one of my first-day joys.
Today, for the first time in a long, long time, I won’t be doing any of that.
Today, I will join my friend, former colleague, and fellow retiree Sharon for breakfast as convocation begins. While my former colleagues sit and wait for each speaker’s words, I will reminisce with a friend who retired two years ago.
How do I feel?
Okay.
I miss my friends already. I miss the fellowship that convocation brings. I will wonder what is being said. I’ll wonder who is boring the audience and who is making their hearts soar.
But I will also relish the freedom of not having to be in a certain place at a certain time for a required period of time.
Teachers are tied to schedules and classrooms.
Those restrictions have been lifted from my life.
Today, I will enjoy breakfast with a friend. Meet with an executive via Zoom to consult on her upcoming speech to investors. Meet with my agent and partner about upcoming business and travel. Take my kids to way too many doctor’s appointments. Help Charlie replace a rug in his bedroom and organize the mess of cords under his desk. Hit some golf balls at the range. Ride my bike. Write. Maybe even finish my book proposal.
Not a bad way to spend a day.
Different, for sure, and missing some of the things I once loved, but I think I can love this life, too, absent the structures, schedules, and rhythm associated with the school day.
Absent a lot of things I loved, but good, too, I think. Maybe even great.
At least I hope so.
