The 2026 Spring Bulletin featured a Faculty Q&A highlighting Caryn Olson. Read it below.

What or who inspired you to become a teacher? 
I was fortunate to grow up attending a school similar to Rye Country Day, where I had many impactful teachers that I still think about more than thirty years later. That experience certainly planted the seed, but it was my father, an educator and school leader himself, who truly inspired me. His stories from school life, shared around the dinner table each night, made the world of education feel meaningful, fun-loving, and important. I looked forward to those conversations, and, in many ways, they quietly shaped my path.

Still, I didn’t take a direct route into teaching. In college, I double majored in Business and Psychology with plans to pursue a career in HR. After graduating, I took an analyst position at a Fortune 500 company, but it never felt right. One day, my (now) husband came to pick me up for lunch, looked around my office, and asked, “What are you doing here?” Without hesitation, I replied, “I have no idea.” In that moment, everything clicked.

That summer, I enrolled in a graduate program in Curriculum and Teaching and took a job in admissions at a private school in New York City. I soon transitioned into the classroom, and the rest is history. Afterward, my dad simply said, “I knew you would find your way.”

Looking back, my inspiration came from a combination of things: a meaningful education of my own, supportive parents who gave me space to figure things out, and people in my life who asked the right questions at the right time. I’m grateful for it all.

What is your favorite part of teaching fourth grade?
There are so many meaningful aspects of the fourth-grade curriculum that never lose their impact. Highlights include our interactive math program with Class Economy and our Language Arts unit on Social Issues, both of which challenge students to think critically and solve problems in authentic ways.

That said, my favorite part of teaching fourth grade goes beyond the curriculum. As a Lower School homeroom teacher, the word “home” truly matters. Before any deep learning can happen, it’s essential to create a classroom environment where everyone feels safe, known, and valued. When that sense of belonging is established, the real magic happens. Students feel comfortable taking risks, celebrating successes, and supporting one another through challenges. All of us working together to build a classroom community that is both supportive and joyful is, and always will be, my favorite part of teaching.

Do you have one standout example of COURAGE from this past year?
Courage shows up in many ways each day in the Lower School, but one standout example comes from our Lower School Morning Meeting. As the oldest students, fourth graders take on the responsibility of hosting those meetings. It is an important leadership role that includes preparing during recess and speaking in front of a large audience of students, faculty, and families.

For some students, public speaking comes naturally; for others, it can feel overwhelming. One student in particular was initially very anxious about hosting and asked if he could take more time to observe before taking on the role. That decision alone showed real self-awareness and courage.

A few months later, when his turn came, he truly rose to the occasion. He gladly sacrificed recess time to prepare, accepted feedback thoughtfully, practiced at home, and worked through his nerves. In the end, he delivered a presentation he should be proud of.

What stood out most was that his courage wasn’t just in standing up to speak—it was in recognizing what he needed, advocating for himself, and then following through with perseverance and hard work. It was a powerful reminder that courage often involves both vulnerability and determination, and that we are all capable of doing difficult things. Well done, Wildcat!!

Grade 4 is the “senior year” of Lower School, which is a special leadership role early bearing lessons in responsible citizenship. What does that look like in daily school experiences for fourth graders?
As the senior members of the Lower School, fourth graders step into a meaningful leadership role that carries both honor and responsibility. Early in the year, we mark this transition with a dedicated Leadership Day in September. On that day, students come together to reflect on what it truly means to be a leader. They explore questions such as: What makes a good leader? What traits do impactful role models possess? And what choices will we make as leaders in our community?

Leadership Day concludes with the creation of a class motto, words that guide the fourth grade throughout the year. This year’s motto, displayed proudly in the hallway, is: “A true leader is not measured by the size of their strength, but by the size of their heart.” This message becomes a touchstone for how students approach their daily interactions and responsibilities.

Throughout the year, students deepen their understanding of leadership in a variety of ways. They meet with Upper School Peer Mentors, who candidly share real-life examples of what it looks like to be a role model in everyday settings - whether in the classroom, the cafeteria, or the hallway. 

Guided discussions, often facilitated by Dr. Barker, present students with realistic scenarios that encourage thoughtful reflection and conversation. These moments help students consider challenges to “stepping up,” explore different forms of leadership, and recognize that leadership is not always loud or immediately visible.

Most importantly, fourth graders are given daily opportunities to live out these values. Whether working with Pre-K and Kindergarten buddies, engaging in book club discussions, or playing together at recess, students practice empathy, responsibility, and initiative. In these small but meaningful moments, leadership becomes not just a concept, but a habit - one that shapes their experience as the leaders of the Lower School.

Problem solving is a critical skill for success in our ever changing world, and it involves resilience, collaboration, and confidence. How do you help students develop these attributes in your classroom, and how can families support this growth at home?"
At Lower School Curriculum Night each fall, I like to share a piece of advice I first heard early in my teaching career: “Prepare your child for the path; don’t prepare the path for your child.” This idea is at the heart of developing strong problem-solving skills.

In the classroom, there is rarely just one way to solve a problem, especially in math. When students share multiple strategies, they deepen their understanding and learn that what works for one person may not work for another. Through partner work and small group collaboration, students practice explaining their thinking, listening to others, and adjusting their approach. Whether they begin with a visual model or an equation, the process matters just as much as the outcome. If answers differ, even better! This gives us an opportunity to analyze where thinking diverged and learn from it.

Problem solving, at its core, is about asking questions, taking risks, offering ideas, receiving feedback, and being willing to pivot. It requires both confidence and humility, and it thrives in a classroom culture where mistakes are seen as opportunities rather than setbacks.

Families can support this growth at home by reinforcing that the goal is not perfection, but perseverance. When children encounter challenges, the most valuable response is not to step in with the answer, but to encourage them to think through what they might try next. Real growth happens when students experience confusion, work through it, and come out the other side with greater understanding. In the end, resilience is built not by avoiding mistakes, but by learning how to respond to them. That’s a skill that extends far beyond the classroom.