Spotlight: Esther Kwon (HI '22)

Growing up in an immigrant family instilled in Esther Kwon (HI ’22) the importance of serving her community and helping others strengthen their sense of belonging: “I chose education because it empowers me to contribute to the greater good with honor and integrity.” The assistant principal received Hawaii’s Milken Educator Award at Daniel K. Inouye Elementary School in Wahiawa on January 31, 2023.

Milken Family Foundation: What do you like about working with elementary students?

Esther Kwon (HI '22): They are incredibly compassionate, curious and creative. It is so rewarding to see students pursuing their wonders, and it has been a joy teaching them how to cherish their inquiries about the world. With answers so readily available and easily accessible nowadays, I find myself honing in on the complexities and types of questions our students are asking. Our students are so resourceful and I know that we will set them up for success if we nurture their skills on asking the “right” questions as they tackle problems facing our global society.

At my core, I believe teaching is about recognizing the infinite potential each student brings, designing meaningful learning experiences and opportunities that help students discover their strengths and passions, and inspiring them to use their talents to make a positive difference in the world. The quality of educational experiences our young children have today will directly impact the brightness of our future.

MFF: How did you end up in education?

Esther: When I was growing up, my parents always emphasized the importance of serving the community. As Korean immigrants, my family and I understood how hard it was to transition into a new life in a new country. We helped several new immigrant families in our neighborhood get set up with their housing, car, insurance, groceries, etc. Naturally, while my parents assisted the adults, I helped their children with school. I tutored them with their ELA homework, introduced them to my own friends, and explained cultural nuances as well as rules to games they’d never played before. I would even get called down from class to translate and calm down a younger immigrant student who would often be in tears. My personal experience as an English language learner gave me the ability to deeply empathize with people through the challenges I had to overcome. I believe this time period in my life was significant in solidifying my values of helping and leading others in a way that strengthens their sense of belonging.

My college experience at the University of Virginia (UVA) further expanded my definition of leadership, finding purpose in serving others, and sense of belonging. I was active in the Asian American student community at UVA. We raised awareness of AAPI issues by hosting educational events for the public, promoting AAPI visibility on campus by coordinating student activities of multiple AAPI organizations, and advocating for AAPI representation for policies and decision-making at the university. It was during this time that I learned that only 2% of U.S. public school teachers identified as Asian American. When Teach For America recruited me, I thought teaching would be a meaningful way to “live out” the causes I had been trying to champion. I applied and was accepted into the 2012 corps. I was placed in the Hawaii region, where I continue to serve today.

I chose education because the field empowers me to contribute to the greater good with honor and integrity. The concept of student self-governance from my university days has also greatly influenced how I operate with my students and my desire to develop good people who are leaders.

MFF: This is your first year as an assistant principal. What has the transition to administration been like?

Esther: My current role prioritizes promoting safety and security on our campus so that positive learning experiences can occur for both kids and adults. As an administrator, I have found a new level of appreciation for all of the different people and role groups that work together to operate a school — teachers, educational assistants, cafeteria staff, office staff, custodial staff, health aides, substitutes, parent volunteers, district and state specialists, and more. It has been eye-opening to see the level of communication and collaboration our teams engage in every day and how critical it is to foster strong stakeholder partnerships as a school leader.

My first year as an assistant principal has been about 1) adapting quickly to the many hats an administrator wears, 2) exercising courage in the face of conflict and navigating each difficult conversation or situation with aloha, and 3) learning how to nurture and support others while holding firm to boundaries and accountability. I am incredibly grateful for the opportunity to serve our school and grow my educational practice and emotional fortitude as a leader. My hope is to honor and strengthen the many gifts our school community members bring to this meaningful work of education.

MFF: How was your first year of teaching?

Esther: That year was when I realized that having good intentions is not enough. Reality check! I remember being passionate and eager to teach and to serve. I took up student council and after-school tutoring while still learning how to be a classroom teacher. I loved my students and expressed genuine care for them every chance I had.

My students deserved the very best, and I often felt like I fell short as a brand-new teacher. I think I tried to make up for my lack of experience and expertise with a lot of time and heart. The positive relationship-building was already there; what I needed were the skills, tools and strategies to help my students achieve excellence. I felt motivated to learn how I could improve as a teacher and better support my students in academics and behaviors.

Thanks to my colleagues and mentors, I was able to grow my teacher toolbox and gain confidence as a teacher. They invested their time and energy into helping me become a reflective practitioner. They joined me in laughter when I shared funny classroom moments and cried with me as I shared my insecurities about navigating a new career in a new place. I am so grateful to them for being there for me. I strive to provide that same support for other teachers as well.

MFF: You have mentored many new teachers. Why is this role important?

Esther: Mentoring is all about increasing new teachers’ efficacy as problem-solvers and decision-makers. When you are a new teacher, you may not even know what questions to ask or the range of support that is available to you. As a mentor, one of the first things I do with my mentee is to explain what types of support I can provide and what they can ask me to do: share or model effective strategies, observe lessons and collect data, analyze observation data, guide teacher reflection, co-plan routines/procedures or lesson plans, role-play scenarios, observe a colleague together, attend professional development together, etc. I give the analogy of having Siri on your iPhone, where its effectiveness will depend on the user’s engagement with it.

The most powerful role of a mentor is facilitating reflective conversations. A mentor guides new teachers on what they need to look for, what to prioritize or focus on, and who and how to ask for what they need in order to mobilize their next steps. The mentor is modeling the flow of questioning, thought processes, and problem-solving skills that reflective practitioners engage in consistently. Over time, the new teacher begins to internalize the different reflective framework and is able to think through questions and next steps on their own while routinizing the celebration of successes along the way.

In truth, all teachers benefit from opportunities for mentorship, collaboration and networking both within a school and across schools statewide. Teachers need to see great examples of what’s possible, be invited to a space to share innovative ideas without judgment, and have access to a support system that reminds them of their “why” during the toughest days. Mentoring is critical in increasing positive collaborative exchanges for new teachers, which in turn will retain talent for our schools.

MFF: Who are your role models?

Esther: I have met so many brilliant educators and role models in Hawaii during my first decade in education. I am who I am today thanks to all of the wonderful educators I’ve had the privilege to cross paths with in Hawaii:

• Jill Baldemor and the entire Teach For America Hawaii team for the incredible work they do every day for our keiki in Hawaii
• Jan Iwase for leading the charge on innovative and reflective practices in education
• Yuuko Arikawa-Cross for her organization, trust and encouragement as a school leader
• Leslie Toy for her unwavering commitment to public education and invaluable friendship
• Rachel Armstrong for always modeling firsthand what it means to be courageous, honest and forward-thinking
• Kristin Walje for her loving support and guidance as an extraordinary mentor in this new realm of administration
• Kelly Miyamura for empowering me to embrace my identity as a teacher leader and connecting me to so many more inspiring HIDOE educators like Mathieu Williams, Whitney Aragaki, Kristen Brummel, Derek Minakami, Kristi Oda, Lorna Baniaga-Lee, Lory Peroff, Jonathon and Erin Medeiros, and the list goes on....

MFF: How did you feel at your Milken Educator Award notification?

Esther: I was so confused and shocked, but mostly grateful. Up until that point, I thought we were getting together to welcome the superintendent to our school. In fact, I was the one who sent out a reminder email to our entire faculty and staff about the assembly!

A huge thank you to the Milken Awards team for coming all the way to the islands for the surprise of a lifetime. The Milken Family Foundation has gifted our school community with such a special memory. I can only imagine the amount of time, planning, and work that went into pulling off such an event. I am forever grateful!

MFF: How did students respond to your Milken Award?

Esther: Ever since the assembly, not a day goes by without a student asking me about the Award — how I felt, how happy they are for me, and of course, what I’m going to do with the prize money. It has been such a fun way to engage in conversation with different students as I consider each of their wild and endearing suggestions.

My favorite moment, though, has to be the day after the assembly. A fourth grader dressed up in a blue dress very similar to the one I was wearing at the assembly, with a pearl necklace to complete her outfit. Her classmates let me know that she was dressed up as me, and that they are calling her Mrs. Kwon #2. My heart!

[MEA Senior Vice President] Dr. Jane Foley had shared during an interview with one of our local news channels that one of the goals of the Milken Award is to influence young people and show them how much we value educators: “We want them to go home tonight and say, ‘I’m going to be an educator, just like Mrs. Kwon.’ ” I sincerely hope that many of our future educators were in the audience that day!

MFF: Any plans for your $25,000 Award?

Esther: At our school, students recite the Eagles Pledge: “Take care of yourself, take care of others, and take care of our school.” I plan on using the gift to travel and create special memories for myself, family and friends. That way, I can show up recharged as my best self to better take care of our school. Additionally, I will be saving some of the funds toward my continued professional learning and development.

MFF: How do you define “success” for yourself, and for your students?

Esther: I’ll quote Ralph Waldo Emerson here:

“To laugh often and much;
To win the respect of intelligent people and
the affection of children;
To earn the approbation of honest critics and endure
the betrayal of false friends;
To appreciate beauty;
To find the best in others;
To give of one’s self;
To leave the world a bit better, whether by a healthy child,
a garden patch, or a redeemed social condition;
To have played and laughed with enthusiasm and
sung with exultation;
To know even one life has breathed easier because you have lived —
This is to have succeeded.”

MFF: What do you hope students remember from their time with you?

Esther: I think about this often because I serve a transient student population at a school located on a military base. I hope our students remember feeling seen and valued for who they are and the gifts they bring; the importance of caring, respecting and learning from diverse people and places; and the call to make a difference and create positive change wherever they go.