Overview:
A veteran teacher reflects on his experience living and working alongside Simon Curry, highlighting Simon’s passion for teaching, deep care for students, and commitment to education despite financial challenges, ultimately portraying him as a compassionate and promising educator shaped by strong mentorship and purpose.
During the 2023/2024 school year at Blue Ridge School (my final year of fulltime teaching), I lived in a trailer. ‘A trailer’ wasn’t completely accurate. It was actually a cluster of trailers large enough to house four human beings along with three restrooms, a kitchen, common area and a large front porch. However, our individual rooms were smaller than the dorm rooms our students inhabited. I was given my own wing in that cluster of trailers. I knew I’d have three roommates. I had taught one of them when he was a sophomore at Blue Ridge – Dhruv Mehotra from India. The other two were complete strangers to me – Cassius Christie and Simon Curry. I truly didn’t know a thing about them except they would be every bit as young (in their 20’s) as was Dhruv.
The day I returned from visiting my wife in Annapolis, MD, to move in to my wing of the trailer, I began emptying my little blue Kia of clothing and really small pieces of furniture. On one of my trips out to my car, I saw a young man who looked as if he might be a new student at Blue Ridge. He was carrying an armful of my clothes into the trailer. “Hi, you must be Mr. Dunsmore. I’m Simon.” Talk about making a remarkable first impression. He learned soon enough to call me Dan, but his respect and kindness toward me has never wavered.
In January of his second year at Blue Ridge, Simon was given the opportunity to move into the Middle Boogher apartment in the dorms and become a hall parent. This was a much-desired move that gave him the privacy and space that a young bachelor deserved. That’s where I met Simon on Wednesday evening, September 3, 2025, when I visited the Blue Ridge campus. I took him Monument Brewery’s six pack of 12-ounce Trail Magic Hazy IPA since I knew he was fond of IPA’s.
It was the night before classes would begin in Simon’s third year at Blue Ridge, his third year of teaching anywhere. He had celebrated his 24th birthday in June. I told him that BRS was lucky to have him and asked how long he might stay before moving on. His response, not surprisingly, was thoughtful and heartfelt. “I have friends my age in the finance and business world who are already earning $100,000 more than I am, but several of them hate their jobs. I really love my job. I look forward to going to work every day, to teaching and coaching the kids. I am just sometimes jealous of the money my friends are making.”
Simon also recognizes that teaching at a boarding school is different from any other type of teaching situation. The 24-7 aspects of the job are demanding. He wants to eventually earn a masters degree in education, then possibly teach in a public school. For now, he has no plans to leave Blue Ridge. My hope is that the School can hold onto him as long as possible. I see in Simon a person who genuinely cares about others, who puts the needs of others before his own. This is the stuff that great educators are made of.
After graduating from Haverford High School in Havertown, PA, in 2019, Simon earned a BA in history and political science from the University of Richmond in 2023. His interest in history, and his desire to teach it to others were inspired by teachers Ryan Caviglia and Charlie Withers as well as his mother, who still teaches high school special education. Yet another of Simon’s positive personality traits is that he truly appreciates his mentors.
What made Simon fall in love with Ryan Caviglia’s AP World History class was his dry humor. He also never smiled during the entire month of September. “He commanded respect and made you want to perform for him. You wanted to raise your hand and be right. Over time, he started to unveil his personality and humor, and that caused all of us students to love him even more.” Simon will never forget that every day he wore a white or black dress shirt, a black tie, black slacks, and either a coat or a blazer. In the public-school world, that was rare to see. Simon knew he’d need Mr. Caviglia’s classroom management skills as well as his sense of humor.
Charlie Withers, who taught AP US History, had a very different teaching style that was every bit as enjoyable to experience as a student. This was eye opening to Simon. Different approaches to teaching could be equally effective. Charlie was warm, enthusiastic, and super approachable from the beginning. No frowns in the month of September. He also had unique lessons and activities. “I particularly remember his walking lectures in which he would walk his class through the halls like a tour guide as he lectured.” Charlie’s need for coffee was great as he simultaneously taught fulltime and pursued a graduate degree. That didn’t stop him from always being available for extra help during lunch and after school. Again, Simon learned from Mr. Withers’ example to find interesting ways to deliver his history lessons.
Ryan and Charlie provided nourishment for Simon’s interest in history and made him think about teaching. It’s Simon’s mom, though, who was and still is his ultimate role mode. Simon is one of three sons. “My mom was tough and loving in the same moments. She had to be to survive. How did she pull that off? I think great teachers need that same ability.” Simon considers his mom the best teacher at her school, but he’s not just being a loyal son. All of her colleagues speak highly of her, too, whether they be administrators, fellow teachers or the janitorial staff. “As an emotional support teacher, she understands her kids maybe more than their parents do. She has the patience of a saint.” His mom is now nearing retirement age but feels she has a few more years to give. I met his mom and dad one weekend when they came to visit Simon. I could see the qualities he describes. One final observation Simon makes about his mom’s work as a teacher is that it never seemed glorious, only admirable. I’m not sure I’ve ever heard or read a better description of what it’s like to be an educator.
Simon doesn’t just educate in the classroom. He loves helping young men develop as athletes, too. He coaches football and baseball at Blue Ridge in addition to teaching history. One of the faculty members he shadowed on the day he interviewed in 2023 was Head Football Coach Clint Alexander. Clint was teaching post-WW2 United State history. When Simon visited his class, Clint asked each student to introduce himself, say where he was from, and list one thing Simon should know about the school. Clint then stayed after class to talk to Simon for a full thirty minutes.
“I’m not sure if Clint was officially interviewing me, but he gave me a great deal of his time that day. I might not have so readily accepted the position at Blue Ridge if not for him. He has a larger-than-life personality, and his charisma is profound. When he called me in June to tell me I was going to coach wide receivers, I was so flattered that I failed to realize I had no choice in the matter!” Simon shared a classroom with Clint in his first year and coached alongside him. In his second year at Blue Ridge, the football team would go undefeated and win the state championship. “Clint is the best coach I’ve ever seen and one of the most special people I’ve ever met. He has shown me how to be an effective coach.”
Simon has an infectiously positive attitude, another personality trait that will serve him well in his teaching career. “I try to keep perspective when frustrated. I’m sure my peers in business face similar aggravations. It’s more important to me to enjoy the positive aspects of teaching, of which there are many, rather than dwell on what might not be going so well.” This is great advice for others planning to enter the profession.
In addition to Simon being one of the kindest people I know, he’s also wise beyond his years. He recognizes that AI and new technologies overall pose great challenges as well as opportunities for educators. Advancements in technology have been aspects of teaching since I entered the classroom in 1979 (and obviously before), but Simon sees that those advancements are accelerating. “Teachers and students must find a healthy balance of how to use artificial intelligence in the classroom so that it promotes learning. Ultimately, it is up to teachers to guide their students toward effective uses of technological advancements.” I’m confident that Simon will one day soon find himself in a leadership role in which he’s able to help other teachers navigate these challenges.
During our time in the trailer, we four guys (Dhruv, Cassius, Simon and I, the one much older than the other three), had plenty of chances to talk about life in general as well as specific pros and cons of teaching. Simon took all of that in. He’s quick to add that he’d visit his trailer mates in addition to those already mentioned if he were to go on his own gratitude tour. He considers us mentors. Any mentoring that occurred was unintentional, though. Rather, they were three young men beginning their careers with loads of questions and insightful observations while I was the old guy who had seen and tried some things. As I got all I could get out of my final year at Blue Ridge, and the other three got all they could get out of their first year, we bonded effortlessly. The conversations that sprang from our questions and experiences made for the best kind of mentoring. I learned a great deal from all three of them.
I wanted to commemorate our year together in the trailer so I commissioned my multi-talented sophomore English student Apichot “Juice” Kamonprapasawat from Thailand to come up with an illustration that pictured each of us in the trailer. I then had that illustration printed on blue long-sleeve shirts for Juice and us. I suspect we’ll all wear those shirts proudly and with much love for some time to come.
Simon’s point about low salaries in education is a critical one. While it may be true that educators don’t educate for the money, I think we also don’t have a choice. Yes, okay, it’s a calling. That’s another thing we say, again because it’s the best we educators can offer. But aren’t other higher paying professions also callings? Don’t professional athletes play the game because of their love for the game? Don’t actors and actresses star in movies because of their love of acting? Don’t medical professionals practice medicine because they sincerely care about the health and wellbeing of others? I truly hope Simon continues to teach. If I can convince someone, anyone, some lobbying group, some group of politicians, to see the wisdom in raising teachers’ salaries so that caring human beings such as Simon can educate and care for young people without having to live a pauper’s life, I’ll consider that a great accomplishment.
