Kaila Schwartz takes the stage as Milpitas Unified’s Teacher of the Year

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Milestone birthdays are a staple celebration for many. But for Kaila Schwartz, her 30th birthday was the turning point in her career.

“I know that sounds really weird but around the time I turned 30, my dad reminded me that, when I graduated from Syracuse, I had promised myself that I would give full-time acting 10 years and that if at the end of those 10 years I wasn’t happy with where I was in my life, then I would reevaluate everything,” she recalled.  “And, well, my 30th birthday was that 10-year mark. I discovered that I really wasn’t happy. I was not feeling fulfilled. I felt like I had lost my creative spark.”

So Schwartz applied to the four most competitive Master of Fine Arts programs in the country, got  rejected from all of them, and was offered a job teaching fourth graders how to read Hebrew at a temple in Cleveland, Ohio.

“That’s the job that changed my life,” she said. “I fell in love with teaching, then got my Master’s in education. All of my inspiration came back. All of my creativity came back. My feeling of satisfaction was never higher.”


Schwartz said this zest for teaching has sustained throughout her career, which has been mainly in Milpitas Unified School District. She has been teaching Theater and English for 17 years at Milpitas High School.

“Seventeen years may be a long time to be in one school district ... but I have a strong connection, an affinity, for this community and for my students,” she said.

Schwartz was announced as Milpitas Unified’s 2017-18 Teacher of the Year during the Employee Recognition Celebration on May 30. She will be one of 29 accomplished educators honored at the 49th annual Teacher Recognition Celebration, presented by the Santa Clara County Office of Education, on October 22 at the Heritage Theatre in Campbell.

“I’m still shaking my head in disbelief,” Schwartz said of the announcement, adding it made her feel shock, gratitude, and humbled.

Schwartz was nominated by coworker LeighAnn McCready, Milpitas High School’s librarian.

“I was quite pleased with Kaila's honor,” McCready said. “Oftentimes our hardest workers go unrecognized because they don't toot their own horns.  Kaila does so much behind the scenes and more than many realize.”

McCready has watched Schwartz work hard for students in different ways since she arrived as librarian at Milpitas High School in 2007. She noted the growth of Schwartz’ theater program from one to two classes to a full schedule, her work with students in English as she challenges them to think for themselves, serving as the adviser to National Honor Society students and their coordination of the bi-annual blood drive, and her support of colleagues through her work with new teachers, and just in everyday interactions with staff. Schwartz has participated in the Teacher Induction Program for at least 10 years.

“She's a team player and isn't about the accolades even if they are well-deserved,” McCready said.  

Two of Schwartz’s seniors noted her class as being participatory with a style that makes them want to actively participate. She makes it a collaborative and not a competitive environment where they feel it is a project-based environment about learning, not just getting the points.

“I try to give students a forum to express themselves, and provide a safe space for them to tell their stories, speak their truths, and develop their self-esteem,” Schwartz said of her philosophy towards training students in the performing arts. “I encourage students to build bridges of understanding across all facets of life. And I also foster an appreciation of the arts.”

Before coming to Milpitas, Schwartz graduated from Shaker Heights High School in 1985, received a Bachelor of Fine Arts in acting and directing from Syracuse University in 1989, earned a Master’s Degree in Secondary Education from John Carroll University in 2001, and did her student teaching at Charles F. Brush High School in Lyndhurst, Ohio.


Growing up in the Cleveland area, Schwartz said the path to Milpitas was clearly paved.

“Toward the end of my Master’s program, we had to create a resume and we had to do interviews,” she said. “I participated in the university sponsored teacher fair,  but I also posted my resume on various sites in different states, one of which was CalTeach. The day after I posted my resume on CalTeach, I got an email from Terry Queenan asking for an interview. The interview was scheduled for a week later. He said it would be a 45 minute interview. It lasted over two hours. I flew out a week or two later to see the school and as soon as I stepped foot on campus, I was offered the job.”

Since starting with Milpitas, Schwartz has been credited with developing an award-winning theater program. This year alone, they won third place for the NorCal Thespian Play Festival, First Place/Grand Prize for TheatreWorks’ 1440 Countdown, and a performance spot in the Edinburgh Festival Fringe for 2019. They have also won numerous awards for playwriting at the 1440 Countdown, having performed at six out of seven competitions. Awards include Best Drama, Best Comedy, Second Place, Third Place, and Schwartz was featured in a TheatreWorks video advertising 1440.

There was an extensive application process for the Edinburgh Festival Fringe, and Schwartz said it was great to be chosen since it was such a challenging application process. Of the information covered, Schwartz had to explain what sets her theater program apart from other high schools.

“I run my rehearsals like I would run them with professional actors,” she wrote in the application. “As a result, I’ve had students tell me that the training they have received from me has set them apart in the working world and has led them to greater opportunities than their peers.”

In addition, the application asked where her students went after high school, and  if any of them had achieved any level of success in theater. They also wanted a five-minute video, reviews, letters of recommendation, student testimonials, and her philosophy on arts education.

She noted being chosen was incredibly validating because they were selected from a Board of Governors on the East Coast, who are all theater educators at the university level.


Schwartz said the awards are great to mark their accomplishments but there is a deeper meaning to the participation.

“It’s really important for my theater students to get a taste of the real world of theater,” she said. “I love my relationship with TheatreWorks because it puts me closer in touch with local theater artists, and it puts my students in touch with them.”

The partnership started about 10 years ago when she first brought her students to one of their matinees. They were impressed with how well behaved her students were both during the performance and the preshow workshops. A couple of years later, they started competing in their 24-hour play festival, now known as 1440 Countdown. Soon after that, she was convinced by one of their educational theatre associates to bring the Young Playwrights Project to her advanced students.

“Everyone on their education staff has become a friend and colleague,” she said.

Despite enjoying her job, Schwartz said there are still challenges that she has to work through, including long hours, fundraising, and feeling like she constantly has to prove to people that an arts education is valuable.

“The skills are applicable to every career path,” she explained. “My students live collaboration, they learn creative problem solving, they become quick on their feet, they are able to work with people of all different personality types, and they’re able to stay focused on getting a task done. They also learn how to work under pressure, and they learn how to stay positive while working under pressure. Most important of all, they gain confidence and self-esteem.”

Despite the challenges, Schwartz said the students are what keep her going.

“They have so much creative energy and they want so much to express themselves, and I think many of them are grateful for the opportunity to do that without judgment,” she said.

They keep her so energized in fact that in five years, even 10 years and beyond, she can’t imagine doing anything else. Twenty years later, looking back on her decision to change her career, Schwartz said she never imagined it would lead to this. But she is paid back in full every day by her students.

“I have so many students out there who make me proud every day. I am proud to know them. I am proud of the humans they’ve become. I’m happy that they are finding happiness and satisfaction in what they are doing, whether or not it’s in performing arts. I’m happy and grateful to have been even a small part of of their lives,” she said.

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