As a middle school English department chair and recently licensed United States Coast Guard Captain, Matthew Carolan seeks adventure in life. Whether racing as part of a crew on Liberty or delivering yachts from port to port on the unpredictable waters of the Great Lakes during the summers, he is always learning. “The lake is like an ocean, a saltless ocean, and you have to be careful and steady as you traverse it.” Matthew has spent decades in Traverse City, Mich. where he has written about many of his adventures in Traverse, Northern Michigan’s Magazine. 

Like sailing, Matthew uses his steady hand to lead his English students through timeless classics in his English class. However, he almost didn’t float into teaching.

After graduating from college with a degree in English and minor in Russian, he was hired on as a clerk at a Plaza law firm, but the days in the windowless office grew old, and the desire to teach began to creep into his mind. “I always had the soul of a teacher, and you might say I was called to the profession,” he said. He quit the firm, packed up his office, and set his sights on teaching. Not long after leaving the firm, he began an internship at Pembroke Hill’s intermediate school. For much of the 1992-93 school year, he taught in Ms. Ashley’s fifth grade class, then began to substitute across the division. He found teaching far more challenging than he had imagined, and he loved it. “I found that there are an infinite number of ways to teach a concept to an infinite number of different learners. The challenge never ends, a teacher’s learning never ends.” He also found that the easiest lesson could fall apart with one mistake. 

From there, his teaching journey would lead him to Sarasota, Florida, teaching at The Out-of-Door Academy and to Wilmington, Delaware at Tower Hill School. While in Delaware, he embarked on his master’s degree from Middlebury College’s Bread Loaf School of English. From there he moved on to take his master’s in fine arts, with an emphasis in fiction and literature from Bennington College, where he wrote a novel under Susan Cheever for his final thesis. “The feedback I received from my professors was instrumental in how I provide feedback to students,” he said. “I will line edit, but also provide personal notes of encouragement.” He enjoyed living in Delaware, but his family had a desire to return to Kansas City. “I made a phone call to Pembroke Hill, and the rest was history,” he smiled. That was 20 years ago.

Over the course of the 20 years spent at Pembroke Hill, Matthew has seen the middle school from several vantage points, as a teacher, an administrator and as a parent of two children who have since graduated, Alexander ’16 and William ’19.

“I am proud to have had my children come through Pembroke Hill,” he said. “My belief in this school played out in how they succeeded academically and athletically. From the classroom to the field, they learned about respect, they learned to work hard and never give up, and they learned to be true gentlemen.”

From a teacher’s perspective, he has a profound respect for his colleagues and deemed teaching, “the heart of the school.” Matthew shared, “To be a teacher is easy; to be a great teacher is incredibly difficult. You have to bring your knowledge and energy day in and day out to inspire students, while looking at life from an infinite number of students’ perspectives.” 

From an administrator’s perspective, as Matthew transitioned this year from being the middle school assistant principal to teaching seventh and eighth grade English, he said the goal was to improve the lives of everyone at the school in a manner that kept the school on a steady course. “It’s not always easy,” he said.

He has been reenergized in the classroom, watching his students grow and develop from the beginning of the year to the end of school. “Where they start the year and where they finish the year is impressive, he said.” At first, they may not understand those abstract concepts or the metaphors woven into a novel, but by May, they are giving you examples.” 

Even at the start of this year, the mockingbird in To Kill a Mockingbird was nothing more than a songbird, but they have since ventured into metaphors, discussing the mockingbirds of the world. “I want to hear what they think about the literature,” Matthew said. “After all, it's not about what I think. They must, however, learn how to have that discussion, learn how to arrive at their own thoughts. They must also learn to have a discussion in a respectful way, whether they agree or disagree. I always impress upon them to back up their assertions with passages from the novel. When we are having a discussion and I can remain silent, I feel like I’ve had a great day of teaching.”