Randall Dunn

Cues and Views

Head of Rye Country Day School Randall Dunn, in brief.

Randall Dunn

Home: Rye, NY. Birthplace: Kingston, Jamaica, West Indies. Organization: Rye Country Day School. Title: Head of school. Pronouns: He/him. Significant other: My wife and greatest cheerleader, Liz. Alma mater: Brown University; Harvard University.

Recent recognition: Appointed board chair of the National Association of Independent Schools. Latest accomplishment: Co-chaired the 2025 Heads’ Conference of the New York Association of Independent Schools. Latest contribution to others: Mentor and coach for aspiring school leaders. Hobbies: Basketball, golf, running, strength training, hot yoga, travel and downtime with friends and family. Recent travel or adventure: Christmas in Paris with my wife and youngest daughter. Last book read: My Friends, by Fredrik Backman. Recent unique acquisition: Compression leg sleeves.

Personality profile: Kind, attentive, open-minded, positive and laughs a lot. Moral compass: Lifelong lessons from my hardworking Jamaican mama. How do you define an ideal business relationship? Teamwork, joy and support. What is your greatest joy? My awesome family. What word or phrase do you use far too often? Frankly. What occupation, other than your own, do you most admire? Visual and performing arts. What ingredient is essential to your perfect vacation? Complete physical, mental and emotional disconnection from work.

What was your first paying job? Delivering potato chips to stores. What was your favorite childhood toy or game? Pushing a bike wheel down the dirt road with a stick. What’s prominently featured on your home or office wall? Artwork made by my own children and students at schools where I have worked. What’s the best advice you received in your career? While some issues may feel insignificant to you, they can feel overwhelming to someone else, so respond to all concerns with respect, care and an open mind. What is your go-to source of news and information? CNN’s 5 Things and New York Times Breaking News. What company or organization do you most admire? Médecins Sans Frontières. What world event has had the greatest influence on your life? COVID.

What change would you like to see in the world?

Peace, love and understanding. They aren’t just words.

What message do you want to send out into the world? We all need to take better care of each other. What widely held belief do you reject? Schools should be run like any other business. What mega-trend most excites you? Artificial intelligence. What mega-trend most concerns you? Artificial intelligence.

What title would you choose for the movie about your life? Sturge Town Boy: Lessons, Love and a Purpose-Driven Life. What actor would you choose to play you in the movie about your life? Denzel Washington. Who would you like to spend an evening with, in heaven? My mom, two sisters, brother and niece. As a kid, what did you first want to be when you grew up? A shoemaker. How would you choose to spend tomorrow, if you knew it was your last day on earth? At home with my family, drinking good bourbon and eating curry goat, rice and peas and a really great salad. What day in your life would you choose to re-live? The day I reconnected with my wife, eight years after we graduated from Milton Academy. What period in your life would you do differently, if you could? My late forties, when I forgot the importance of work/life balance.

Personal motto: "I am the master of my fate, I am the captain of my soul" (William Ernest Henley, Invictus). Favorite quote: "The greatness of a man is not how much wealth he acquires, but in his integrity and his ability to affect those around him positively" (Bob Marley).

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