Ken Kakesako’s professional life was a bit different years back when he was deputy director of Hawaii’s Department of Agriculture. Then, he spent his days at hearings and briefings advocating for agriculture issues. Now, the 36-year-old brings science alive to middle schoolers and is involved with after-school activities that enrich the educational experience.

When the desire to become a teacher hit Kakesako, Chaminade University made it easy for him to continue working while pursing his Master of Education. The program was appealing because he was able to continue to support his family by day and chip away at coursework in the evening.

In his first three years as a teacher at Stevenson Middle School, he’s been instilling his love of science in his students and founded the after-school wrestling club. He obtained a R.E.A.C.H. grant from the Lt. Governor’s office for $5,000 to fund wrestling and robotics and secured $30,000 for next year to go toward all clubs, including volleyball, ukulele and art.

MEd Ken KakesakoHe also worked with McKinley High School students to create ROOTS (Responsible Open-Minded Operations Through Science) at Stevenson and started a science Olympiad team. And if that wasn’t even to fill his plate, Kakesako also helped Chaminade with its accreditation process in by giving a student perspective as someone who had completed the program.

Colleagues and mentors were quick to recognize Kakesako’s enthusiasm and impact he has on his students. He was recently surprised during a weekly staff meeting with news that he was the recipient of the prestigious 2018 Milken Teacher of Promise Award. HawaiiUSA Federal Credit Union sponsors the annual award, which recognizes teachers who excel early in their careers.

“It was a great surprise during the meeting,” he says. “I’m grateful to those that made it possible, I’ve had great teachers and mentors supporting me.”

Kakesako’s mentor and fellow science teacher, Julie Segawa, nominated him for the award and she has a history of mentoring teachers that stand out from the crowd. She mentored another Chaminade graduate, Ryan Kagami, who received the 2014 Milken Teacher of Promise Award.

When Kakesako reminisces about his time spent at Chaminade, mentorship sticks out in his mind. “The best part of my experience was the interaction with professors,” he says. “My mentor, Sheri Fitzgerald, helped me gain knowledge and insight while I was student-teaching.”

Path to finding his passion

Like many, Kakesako’s path to his where he stands today included many twists and turns. After graduating from ‘Iolani School, Kakesako left Hawaii and earned his bachelor’s in Economics from Harvard University.

He then spent just over five years working in Japan. First, he taught English to middle school students and then he was a recruiter for an investment banking company. When it came time to start a family, Kakesako knew he wanted his children to grow up around family and share similar experiences he had growing up in the islands. So it was time to come home.

Back in Hawaii, he worked for the state. He was a legislative administrator and budget analyst for Senator Russell Kokubun and then became the DOA’s legislative coordinator and deputy director.

But returning to teaching kept tugging at him. And when he looked at his options, he choose Chaminade because of the program’s flexibility and emphasize on learning in and out of the classroom. Now, Kakesako uses lessons he learned at Chaminade – like taking concepts taught in class out in the world to make them relevant to students.

Ken Kakesako, MEd“I love it when my students make connections between things they’ve learned to their own lives,” he says. “We recently had a lesson about the super blood moon and many of them went home and shared the information with their parents and were super jazzed when they watched it. Their excitement gives me energy.”

Kakesako brings a myriad of skills to room 208 at Stevenson through the various hats he’s worn. He uses his past experiences in sales to “sell” his lessons to students, knowledge gained from working in government to secure funding for his classroom and after-school clubs and he uses strategies learned at Chaminade to make learning relevant and exciting to his students.

And in the end, it’s those lessons learned in his life that leave the biggest mark.

“I want my students to become educated citizens and exercise critical thinking,” he says. “I teach them to be deeper thinkers and that learning never stops. I’m preparing them for jobs that don’t even exist yet and hope that I am setting them up for a lifetime of learning.”


The Master of Education program offers concentrations in Educational Leadership, which prepares candidates for administrative positions with an emphasis on K-12 schools; Instructional Leadership,which provides advanced knowledge of classroom practices for teachers and other educators not currently aspiring to become administrators; and Child Development, which offers advanced study of developmental theory, research and application.

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