Gaylynn Nakamatsu
Kindergarten Faculty
Related: In Good Company: Cindy Murillo
For Kindergarten Faculty Gaylynn Nakamatsu, teaching is more than a career – it’s a lifelong journey of discovery and growth. Over her 15 years at Punahou, she’s cherished watching early learners grow into confident, curious and compassionate young adults. In recent years, she has experienced full-circle moments when former students return to visit her during their senior year in the Academy. “Seeing them ask insightful questions, think creatively, and collaborate shows their growth as individuals,” Nakamatsu reflects. “It reminds me of the journey we share and the role I play in their lives, even as they move on to new stages.”
In her free time, Nakamatsu enjoys culinary adventures with her husband, Aaron, and visiting her daughter, Gabbie ’24, who is in her first year at Santa Clara University. She also dotes on her beloved Chihuahuas, Gidget and Burrito.
How has your teaching approach evolved over the almost 15 years you have been at Punahou – especially when it comes to encouraging students to take risks?
In the early years, I focused primarily on creating a structured environment that emphasized the importance of mastering foundational skills. While this was essential, I soon realized that true learning often happens when students step outside their comfort zones and embrace the possibility of failure as part of the learning process.
Over time, I made a deliberate shift towards fostering a classroom culture where risk-taking was celebrated rather than feared. I began by intentionally designing lessons that challenged students to tackle unfamiliar problems, think creatively, and express their ideas without worrying about being “right” all the time.
When you get students in kindergarten, they are not familiar with the school – how do you create a sense of community in your classroom?
I focus on building relationships with each student while also fostering a sense of belonging among the whole class. Because they are joining such a large community of learners, we start small and slowly expand their connections.
At the start of the year, we introduce a variety of welcoming rituals that help students feel comfortable and valued. One of the first things we do is spend time getting to know each other through simple icebreakers, like sharing our names, favorite colors or ice cream flavors. We make sure to engage with each student individually, allowing them to feel seen and heard, which helps establish trust early on.
How do you create an environment where students feel free to dream and discover?
We believe that students need the freedom to follow their natural curiosities and interests. When students are given the freedom to explore topics that excite them, they become more engaged and motivated to dig deeper. We encourage them to ask big questions and pursue their own paths of discovery, which helps cultivate their critical thinking and problem-solving skills. In this way, we also learn a lot from them.
Disappointment is part of life, how do you help students find ways to be resilient?
One of the first steps we take is to normalize disappointment as part of the learning process. We emphasize that it’s okay to feel upset or frustrated when things don’t go as planned – these emotions are completely natural. By validating their feelings, we help students understand that it’s not the disappointment itself, but how they respond to it, that truly matters. This shift in mindset allows students to view setbacks as opportunities for growth rather than as failures.
Your first class of kindergartners visited you a couple of years ago – what was that full-circle experience like?
Two years ago, my first class of kindergartners surprised me by visiting me on their first day of school as seniors. I had the opportunity to reflect on how much they had grown and how far they had come since we first started together. Seeing them visit as older students, confident and excited to return to a place where they once felt so small, was incredibly fulfilling. We shared old photos, stories – and a few tears! Personally, it was also a special moment for me because it allowed me to see the long-term impact of the relationships we had built.
