For six years, he has served as a guiding force for Upper School students, as they take their final steps toward graduation. We sat down with Mr. Cunningham to learn about his philosophy, hopes for students, and diverse talents.

Please share your journey to education with us?
I was 12 years old when I started working with kids as a camp counselor-in-training and I haven’t taken a year off since! In college, I worked at a museum and a zoo while simultaneously student-teaching in a high school. I’ve been a classroom teacher, coach, college professor, theater director, and literary book editor. I’ve discovered that being in a school environment, and specifically working with high school students, is where I belong.

After attending College of the Holy Cross in Massachusetts, where I majored in English, I taught at the high school level for several years before moving to New York City to pursue my Masters in nonfiction writing at Columbia University. I taught at charter schools in Manhattan and Brooklyn before joining Dwight in 2014, where I have taken on additional roles with each passing year.

What is your educational philosophy?
I believe in holistic and experiential education. That is to say: I want students to have a range of educational experiences that match the diversity of their skills and interests. When I hear people talk about school as though it’s not “the real world,” I want my students to know that the considerable amount of time spent in school every day is, indeed, very real and meaningful. 

What do you hope that students gain from taking ToK? 
Theory of Knowledge (ToK) is a cornerstone of the IB Diploma Program designed to teach students to think critically about thinking. During the two-year course, students examine the nature of knowledge, learn to question assumptions, and develop a broader understanding of the world in which they live. I see ToK as 50% academic analysis and 50% self-help, in that it can help students understand why and how they think when they solve different kinds of problems, work in different environments, or relate to different people. 

The course has a great framework from which to begin, and it’s exciting to see how every student’s mind and life impact the dynamic of the course for everyone else in the room. ToK asks students to wrestle with some fundamental questions: What do we know? and How do we know? By answering what may seem like simply stated questions, students reveal a lot about who they are and how they navigate the world through some surprising, personal, and complicated responses.

What was your own experience as a senior? 
I was a high school senior twice! Once in New Hampshire and again in the UK. At the Holderness School in Plymouth, NH, I had a great year in which I pursued a lot of independent work in my classes, while building non-academic skills and habits that have helped me throughout my life. I graduated at 17 and took a gap year to complete my A-Levels at Blundell's School in Devon, England, where I was a boarding student. I had received a scholarship, so at first, it seemed a great way to travel to another country, but the experience turned out to offer so much more. I had only one year to complete a suite of two-year-long courses. That time was a major source of intellectual growth. It truly inspired me in so many ways as an academic, creator, athlete, and citizen — and allowed me to graduate again at 18.

How does teaching inform your work as Dean?
As the main grade 12 ToK teacher, I see almost all of the seniors in my classroom and really get to know them, their personalities, strengths, and skills. This knowledge is extra beneficial both for me and my students when guiding and supporting them as their dean. I also draw on experience I have had teaching 14-18 year-olds for many years, so I keep in mind the entire arc of high school — the whole journey — when supporting them as it comes to an end. If there is a common thread that guides my work, it is helping students to understand the power of taking responsibility for one’s actions and efforts, so that they can grow into the people they hope to be.

Seniors face many challenges — college applications, IB exams, graduation. How do you help them navigate?
The best thing I can do is listen and collaborate. I try to offer my best advice and perspective, and know that 17- and 18-year-olds don’t lack for people telling them what to do. I try to hear where they are, find out where they are trying to go, and light the way as best I can. 

During this challenging year, there are things beyond students’ control at the time they want to be most in control. By having an open door, open ears, a presence in the classroom, a little bit of humor, and a clear set of operating rules, I try to help them understand how they can best use the control that they do have. At the end of the year, when we celebrate all of their achievements, we’re proud to know that we’re sending them off to embark on the next leg of their educational journey as well-prepared as possible.

Tell us about your passion for kickboxing and Dwight’s program.
I’ve been doing one kind of martial art or another since I was six years old, barring a highschool pause to play lacrosse, when I learned to use sticks instead of fists. Kickboxing — Muay Thai specifically — is arguably the most intense form of striking martial art. The discipline plays a large role in my life. First and foremost, it’s a visceral outlet for the intensity and competitive streak I have, which don’t factor into my work cooperating with and supporting others. Muay Thai is also a thrilling challenge and offers opportunities for personal growth and learning. I am inspired regularly by the depth, subtlety, and creativity of the experts in the sport.

I have coached kickboxing before at other schools, but the best fit for me is doing so here at Dwight. When I first came, former P.E. teacher and Security team member, Eddie Purovic, had been running an after-school boxing program for over a decade. Despite being much better and more experienced than I am in coaching, Eddie kindly let me take over after a little while. I really enjoy sharing my passion with students, and kickboxing is a phenomenal way for a teenager to learn about him/herself, gain self-discipline and strength, relieve stress, and benefit in other positive ways. 

Your bio mentions doing voiceover work. Tell us about that!
I sang a lot in high school and college. When I voiced Audrey 2 (the carnivorous plant) in my high school production of Little Shop of Horrors, I was bitten by the voice-acting bug. I have narrated a few books and short pieces over the years, sometimes professionally and sometimes amateur, on stage and recorded. Probably my most exciting voiceover job has been announcing  Dwight’s annual global concerts in New York — and getting to hear my own voice through the speakers at Carnegie Hall! It’s been a real honor. The concert will again return to Carnegie Hall this year and maybe I will have the chance to do so again!

What’s your spark of genius?
I’m fascinated by understanding, explaining, and navigating the larger dynamics of whatever context I’m working in. Whether I’m analyzing an essay, mediating a conflict, or sparring in martial arts, I’m always thinking about what everyone’s expectations are ... about how their assumptions align with the standards and rules of a given situation — or don’t. That might sound complicated, but it just means that I Iike to figure out what the “rules” are wherever I find myself and how to play within and improve those rules if possible. 

What’s a little-known fact about you?
Perhaps it’s that I’m a native San Diegan. Most people don’t know that, but dude, the long hair, cowboy boots as formal footwear, Baja California accent when I speak Spanish … it seems a little obvious to me!

What is obvious is that Mr. Cunningham is dedicated to lighting the way for seniors, as they finish their high school journey and prepare for all the amazing opportunities that await them!