On My Mind: Reflections from Head of School Randall Dunn

2025-26 HEAD OF SCHOOL'S AREAS OF FOCUS

Mr. Dunn shared his areas of focus for 2025-26 in his first On My Mind message on November 7, 2025.

Dear RCDS Parents and Guardians,

As we enter the season of Thanksgiving, I want to take a moment to share my immense gratitude. What an incredible October we had at RCDS! We celebrated a terrific Wildcat Weekend & Reunion, achieved new records in the Annual Giving Challenge, and welcomed an impressive number of prospective families to our Admissions Open House. Amidst all of this excitement, our daily pursuit of academic excellence and the development of purpose-driven passionate learners continued in full force.

If you have been in my office, you likely know that Invictus by William Ernest Henley is my favorite poem—I have it framed behind my desk near a photograph of my mother. As an educator, Henley’s seminal work has always resonated deeply with me. It is about resilience, courage, and carrying on with an unwavering sense of purpose no matter the challenge.

This year, as we explore courage as a school, I am filled with hopeful optimism. We are talking about the courage to make authentic connections, to lift our heads from screens and away from social media, to seek knowledge, and to create ambitious plans for our future. At a time when bleak outlooks seem to abound, it takes courage to consider the possibility of brightness through excellence and undaunted care for our students.

I was reminded of this at the Alumni Hall of Fame dinner where we honored six new inductees—alumni, faculty, a coach, and even a team! Each and every one of these RCDS ambassadors demonstrated their own brand of excellence that is fueled by integrity, purpose, and courage. I urge you to read their stories and listen to their speeches here.

On a day-to-day basis, our theme of courage resonates across the School and—as the example of our alumni, teachers and former teachers shows—a Rye Country Day education is life changing, and it requires us all to make a difference. And that is just what we do.

So to borrow from Henley and make a Wildcat edit: I am so thankful for the unconquerable soul of our students and our school. Our focus and our work are inspiring and vital.

Thank you for all that you do for RCDS.

Go, Wildcats!

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,

As you may know, I meet with seniors regularly to discuss their observations of RCDS and other topics. Recently, at one of these "Senior Circles" meetings, I found myself buoyed by their impressive self-knowledge, their astute observations, and their genuine commitment to community (knowing these admirable young minds are poised to lead our world left me with a sense of assured hope).

The students' focus on their educational progress and aspirations beautifully reflected Rye Country Day's hallmark commitment to academic excellence. Their thoughtful counsel on ways to keep our community close knit and strong was a clear indicator of their love for this place.

Our seniors have a strong sense of what makes RCDS special—the rigor of our program, the support of our community, and our guiding compass that compels us to always ask how we can be of service. By this time next year, they will have made their marks as leaders at their institutions of higher learning. Here at RCDS, we will honor them by staying true to our core, and we will always be the school they are proud to call home.

Another 2025 RCDS "graduate" is Dr. Meredith deChabert, Assistant Head of School for Academic Programs, Institutional Research, and Data. She will be addressing our seniors as their commencement speaker before her coastward move to Rhode Island to become the next Head of the Gordon School.

Like our seniors, Dr. deChabert knows the heart of RCDS and will forever be a part of our wellspring of excellence. Surely, all of us at commencement will be misty-eyed as we bid farewell to these outstanding members of our community. Lucky for us, RCDS connection endures generations and transcends physical separation. Once a Wildcat, Always a Wildcat!

The long weekend is coming up, and although the weather may not be what we'd wished for, I hope you take some time (rain or shine) to reflect on what it means to be a Wildcat. And, I hope you share your love and gratitude with those you admire.

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,

Spring Break has officially arrived, and our Upper School musical cast and crew members have put into song what most of our students are surely feeling!

As we head into Spring Break, I want to express how incredibly proud I am of our RCDS community. Since we returned from Winter Break—which seems like just yesterday—our students have accomplished so much and our community’s connection has been strong. Here are a few community highlights from last three months, which you can read about on our website news feed:

• 30th Anniversary Festival Chorus Concert
• Winter Wildcat Day
• GEBG Student Action Summit: Arts and Innovation for an Equitable and Sustainable Future
• Young Physicists Tournament
• Family Skating Party
• Grand Opening of the We Are RCDS: Bridging, Belonging & Building Community exhibit in Partnership with Common Circles
• Debate Tournament
• Upper Musical - Head Over Heels
• Middle School Musical - The Lightning Thief: The Percy Jackson Musical
• Upper School Exams - and exam treats and games from the PA!
• Winter Sports Awards, which concluded a terrific winter athletic season!
• Kindergarten and Grade 1 Concerts
• Middle and Upper School 3D Art Show

And these events are IN ADDITION to the outstanding daily work of our students, faculty, and staff, as well as the supportive partnership of our parents and guardians!

Each and every day, I am inspired by the achievements and attributes that define our remarkable school—kindness, joy, dedication, resilience, curiosity, and a sincere commitment to making our world better and brighter. Thank you for leading by example, RCDS! 

I hope you and your children enjoy this well-earned Spring Break. Be sure to spend time with loved ones, and make the days joyful, restful, and reflective. We will see you in a couple weeks, ready for the homestretch of our year of connection.

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,

Being in a school environment is perfect for generating a magical mix of inspiration and excitement. I frequently find myself looking back with gratitude for what has passed and eagerly looking ahead to what is next. As the parents/guardians of our wonderful students, I know you understand this special combination of emotions.

With Winter Break approaching and with the new year on the horizon, I am feeling particularly inspired by the amazing learning that took place at our school this past fall and excited about the upcoming second half of the academic year! I am also feeling extremely grateful for our community and the CONNECTION we all share as proud Wildcats.

Thank you for your partnership and for entrusting us with your children and your family’s educational journey. Next year, we will hit the ground running with another Conversations with the Head presentation on January 15, this time centered around Competency-Based Learning (CBL) and the great, lifelong skills it offers students. Learn more about CBL here.

I also look forward to sharing the annual State of the School Presentation with you on Thursday, January 30, at 8:30 a.m. I will provide updates on my areas of focus, including the Master Plan and the AP Task Force’s summary of findings and proposed curriculum adjustments, among other topics.

January will also gather us for meaningful community events including the MLK Day of Impact, Festival Chorus, the Green Screen, Winter Wildcat Weekend, the Family Skating Party, and more. How fortunate we are to share this vibrant learning community!

I am sure your Wildcats at home are counting down to their well-deserved break—one more day (reminder: it is an all-school pajama day!).

I wish you and your loved ones a restful break and happy holidays.

Yours,

Randall Dunn
Head of School

2024-25 HEAD OF SCHOOL'S AREAS OF FOCUS

Mr. Dunn shared his areas of focus for 2024-25 in his first On My Mind message on October 28, 2024.

Dear RCDS Parents and Guardians,

Wow—the past two weeks at RCDS have been absolutely wonderful. From a perfect Wildcat Weekend to the record-breaking Annual Giving Challenge and our most well-attended Admissions Open House to date, RCDS CONNECTION has been front and center. It has warmed my heart to see our Wildcat family gather so joyfully to build spirit, support RCDS, and share what makes us proud of our school. Thank you!

As November approaches, I am thinking—as I am sure you are—about the upcoming national election. Like many of you, I am keeping up with the news, I am making my plan to vote, and I am thinking about the impact of the election on our nation’s—and more specifically our school’s—young people.

At RCDS, we are always guided by centering our students’ education, their well-being, and their ability to engage in compassionate, critical thinking. As we prepare for the election, we are taking an academic and community approach that elevates learning and rejects divisive rhetoric or unproductive discussions.

Dear RCDS Parents and Guardians, 

On this Spring Break eve, I want to share the overwhelming sense of gratitude I feel for our community. Spring is a time that conjures regeneration and exciting new growth, and I see us growing together every day.

I have seen the hard work of our students, faculty, and staff over the winter months come together, and the results are terrific—concerts, musicals, championships, community events, service projects, and, yes, even exams! I see the nurturing partnership of our families that helps us all grow even stronger. The dedication of this community is quite a sight, much like the daffodils we all admire at springtime. 

This Spring Break, enjoy your time with loved ones. Make the days joyful, restful, and reflective. We will see you in a couple weeks, ready for the homestretch and our continued journey together!

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,

When a new year approaches, we tend to raise our gaze to imagine the road ahead. I am inspired to share my thoughts because I have high hopes for the new year and for the future in general. I feel this way because I am surrounded by our students.

It’s quite hard—near impossible—to feel anxiety about the future when you see daily the amazing qualities of our students. They are thoughtful, compassionate, kind, curious, and capable young learners. Watching them engage with each other and with the adults at school gives me assurance that the future is in good hands—their hands!

I recently read You Will Do Great Things, one of my favorite children’s books, to our Pre-Kindergarten class. They were listening intently and their eyes lit up at the range of exciting accomplishments that life can offer. They are ready for a bright future. When I visited a fourth grade classroom, each student shared their favorite parts of themselves with their classmates who nodded and cheered. I found this activity profoundly moving. Our students feel proud and valuable, and they are incredibly self-aware. They also know the value of listening and caring. Minds like that will make the future bright.

Sixth graders in Ms. Henerey’s drama class delighted and impressed me with their ability to try theatrical exercises that tested their creativity and processing speed—I learned their minds work much faster than mine! Our Upper Schoolers, those closest to going off into the world to be the next architects of the future, have inspired me deeply with their earnest passion, their willingness and ability to engage critically, and the deep integrity of everything they do. With young leaders like this poised to go forward, I have high hopes. And I have endless gratitude for being a part of the educational journey preparing them for the years ahead.

I wish you and your loved ones a restful break and happy holidays. Thank you for entrusting us with your wonderful children. Educating them is our greatest privilege. They are our beacons of hope.

Yours,

Randall Dunn
Head of School

2023-24 HEAD OF SCHOOL'S AREAS OF FOCUS

I have shared with you that at the start of each school year I develop areas of focus to guide my work as Head of School. September and October are about workshopping my ideas and November and December are about finalizing the areas of focus. This process intentionally resembles the work of teachers and students as they develop routines in the fall and hone in on clear goals after that first round of conferences in November. Please scroll down to view my 2023-24 Areas of Focus, which I look forward to discussing in depth at the State of the School presentation in January.

Dear RCDS Parents and Guardians,

Here we are looking at Thanksgiving Break and then December in the not-so-distant future! The start of the holiday season feels like a milestone in the school year. Reaching a milestone never happens by accident; it takes a great deal of intention, care, and human energy. 

This is why the respite and warm embrace of school breaks are so important—time offers us a chance to recharge, recenter, and rededicate ourselves to our intentions. I hope you are all eagerly preparing for a joyful Thanksgiving, full of time well-spent both in community and in reflective self-care. I know I plan to make headway on my latest puzzle. Stay tuned for a progress update!

Something that underpins my daily work and my annual intention setting is our all-school theme of KINDNESS. We often hear about the benefits of Random Acts of Kindness (RAK). If you have practiced or been the recipient of RAK, you understand. But for those of us who have committed to actionable kindness, this practice came in the least random way. Intention, care, and planning go into building and sustaining this good habit.

I have been heartened by our students who, inspired by the year’s theme, are choosing and creating very real moments of kindness. A thoughtful thank you card, a high five, morning meeting shout-outs, an assuring smile, cheers for their peers at the board, on stage, or on the field; an understanding gaze during hard times, a joyful holler in good times—the list goes on. Our students’ intentional kindness will have lifelong benefits for them as individuals and for us as a community.

At this particular time in history when our world is heavy with tragedy and pain, acts of kindness can soothe, uplift, and heal our spirits. Practicing kindness creates meaningful moments of connection that help us recognize and celebrate the common ground in our shared humanity.

I am so proud our community is putting its energetic focus behind the pursuit of such a meaningful practice. The world needs kind people and that’s just the kind of people we are at RCDS! 

Happy Thanksgiving!
 

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,

The home stretch of the school year is an exhilarating time. There is much to anticipate, and much to get done! Students and teachers are wrapping up and showcasing class projects, seniors are preparing to graduate, eighth and fourth graders are getting ready to move up a division, sports teams are battling it out in the postseason, visual and performing artists are sharing their work, and much more!

As a former track athlete in high school at Milton Academy, I have a real appreciation for the finish line and the achievement it encourages. What’s particularly interesting about the finish is that it is often nowhere in sight at the start—and runners know that you can “picture” it in your mind, but you’d be remiss to think about it too much at the blocks. You have to stay in the moment, focused on your start, trusting that your teammates in a relay will run their hearts out, and that the finish line will appear in all its glory at just the right time.

By now, you know that another favorite pastime of mine is jigsaw puzzles (yes, it’s quite a ways from running, but bear with me!). In the fall, I began a wooden puzzle with non-traditional pieces—no edges or corners easily apparent, just swirling, mind-boggling curved carvings. I decided to place it in my office and invite students, parents, teachers, and staff to help. 

At a certain point, it seemed like it would never get done. In fact, it was daunting to even get started. Then I remembered the lessons from my running days, and I chose to think less about the finish line and just “stay in the moment.” Lo and behold, through teamwork, strategy, and perseverance, piece by piece came together.

Finishing the puzzle and crossing the finish line on the track are different tasks that deliver similar lessons: 1) Many minds accomplish incredible things, and 2) Not knowing how a process will culminate should not deter you, it should inspire you. Every academic year concludes with heart-warming reminders of the many lessons, achievements, hurdles, and dreams experienced by all constituents of the school. I love the exhilaration of this dash to the finish. With the long weekend coming up, I hope you enjoy the extra time with loved ones and take moments to reflect on the many accomplishments of this school year. When we get back that finish line will be even closer! Yours, Randall Dunn Head of School

Dear RCDS Parents and Guardians,
 
We returned from Winter Break refreshed and ready for more teamwork. Then we blinked … and here we are—two days until Spring Break! Time’s capability of shrinking and expanding has always mystified me. A lifetime of working in schools has only cemented my belief in the almost magical and mysterious quality of time. It is clear to me that “time” never really changes. How you spend it is what matters most. So, what have we done with this winter time we have shared together?

The academic schedule continued, culminating with trimesters ending in the Lower and Middle divisions and March Exams in Grades 7 - 12 (to our exam takers—remember to be proud of your accomplishments; we are very proud of you).

The winter athletic season roared in and out with impressive performances from our Wildcats, including double championships for the Boys’ Squash team. Our stages lit up with terrific performances. Festival Chorus, The Addams Family, and the Grades 2-4 Winter Concert brought us together in admiration of the passion of our performers.

We also nurtured our minds and community through workshops, field trips, conferences, service projects, and festive gatherings, including Winter Wildcat Weekend and the annual Arts Festival & International Fair. This list comprises just a few of our learning experiences since the last time I wrote you. I gaze with wonder as this incredible community makes so much out of every second, minute, hour, and day.

Mindful reflection is something many of us reserve for milestone moments (the end of a year, the beginning of a break, etc.). There is value and sense in that. I also want to encourage us not to wait—to take the opportunity to thoughtfully consider the small moments that can pack a lifetime’s worth of wisdom.

A reflective ritual I particularly enjoy is senior circles, meetings I have with small groups of seniors to discuss their observations of RCDS. These young leaders are at an inflection point in their lives. Their insight and drive inspire me. They are living every moment fully in the present while eagerly looking ahead to the future—all the while keeping and growing from the lessons learned in the past. These conversations with our seniors help me learn about RCDS’s strengths and areas of opportunity from the student perspective. They also serve as a reminder that we should ALL be living every moment of our lives like it is our senior year.

Every day is an opportunity to roll up our sleeves, dig in, pause, look back, and look ahead with ambition. Let’s do that RCDS, whether on vacation or at school. Have a wonderful, restful, and reflective Spring Break!

Yours,

Randall Dunn
Head of School

Dear RCDS Parents and Guardians,
 
With four days until Winter Break, the sense of accomplishment is all around. Through enthusiastic teamwork and a whole lot of spirit, we have arrived at the conclusion of the first half of the school year. There is a lot to feel good about—from the impressive work of our students in classrooms and theaters and on fields and courts to the partnership of our wonderfully supportive parents and guardians and the dedication and hard work of our faculty and non-teaching employees.

I recently had the pleasure of being interviewed by first-graders during their community unit. Their questions demonstrated the curiosity and open-mindedness that characterize childhood. They were so eager and willing to learn. This of course was adorable, but more so, it was a deeply inspiring reminder that our charge as a school is to harness and extend that curiosity and willingness to explore new ideas. This is what a lifelong love of learning is all about.

The door of my office is adorned with a metalwork sculpture of the RCDS seal, which features the oak tree in the center. I look at and think about this tree daily. It’s a striking representation of our work as a school community. At graduations and milestone moments—like the first-grade community interviews—we can see in our students the brilliant branches and far-reaching nature of their critical thinking, creativity, and ambition.  We can also appreciate all of the time and nurturing it takes for that growth to occur. 

To thrive, a tree needs healthy soil, just as students need a supportive community. To sustain strength through the seasons, tree roots must be deep and interconnected, just as students must feel a firm sense of belonging and nurturing care from peers and mentors. With all of these elements in place, the inevitable changes of each season are not challenges to the tree or student’s well-being, but opportunities for new growth.

As you head into your well-earned break, take some time to reflect on all of the growth of the first half of the school year, and the role each of us has played in the journey. It is a joy and privilege to be in community with you. The soil is healthy, the roots are strong, and the result is indeed brilliant.

I wish you and your families a joyful holiday season and a restful Winter Break. 

Yours,
 
Randall Dunn
Head of School

Sustained Focus on My Transition to RCDS Community

Advance Three Significant Institution-Wide Initiatives: Strategic Plan, Master Plan, and NYSAIS Accreditation

The Strategic Plan is underway. The Assistant Heads of School and I are working to assign committee leadership, identify action steps, and codify accountability and success measures. Working with Pam MacAffer, Assistant Head of School for Finance and Operations, consultants and members of our community, we will design the next RCDS master plan. This work will ensure that the progress we make pertaining to the strategic plan is complemented by the appropriate campus spaces. Dr. Meredith deChabert, Assistant Head of School for Academic Programs, is spearheading our self-study as part of our NYSAIS ten-year accreditation, and I will support her as necessary in this important process.   

Partner with Parents and Guardians

Dear RCDS Parents and Guardians,

I hope these beautiful—albeit chilly—October days are finding you well. Last week, I had the pleasure of seeing many parents at the PA’s fall luncheon. It was a lovely event that centered home-school partnership and the community we are all so fortunate to share. Indeed, as the most significant areas of our students’ lives, home and school must always be connected. In this second month of the school year, I feel we are living up to this quite well. From our divisional curriculum nights, discussions with counselors, and one-on-one conversations with teachers/advisors to grade-level receptions, athletic games, and joyous school events like the Block Party and PA luncheon, our lines of communication are open and active. 

In the spirit of continuing to build our relationship, I will periodically reach out to share what's on my mind—reflections and ideas that I hope will nurture our home-school connection. Today, I am sharing what I have articulated as my areas of focus for my year 1 at RCDS. At this point in the calendar, I finalize these areas of focus for the year, just as I know that students are also working to establish their goals with their teachers.

Though these "On My Mind" messages will not be urgent per se,  I hope you enjoy receiving them as much as I enjoy writing them. Through notes like this and our other numerous school communications and events, I believe we will forge a productive and robust partnership. Here we are, Rye Country Day … October!

Yours,

Randall Dunn
Head of School