36-year ‘magical career’ with MUSD coming to close for Diana Orlando

When the 2022-23 school year comes to an end in June, elementary school educator and teachers’ union leader Diana Orlando’s “magical career” in education will conclude after 36 years with Milpitas Unified School District.

“It truly is a family here,” said Orlando, who started as a substitute teacher for Rose Child Development Center (CDC) in March 1987. “I have made some of my closest friends here in the District. They are now my family.”

Orlando’s educational pathway quickly went from part- to full-time when she was hired September 4, 1987 as a preschool teacher and head teacher for the what was referred to as the “latch-key programs” before being hired as a Science Specialist, splitting her work day between Sinnott and Curtner elementary schools.

“MUSD has always been a cutting-edge District and always puts students first,” Orlando said. “We give out staff freedoms some Districts would never allow. We have been a collaborative District whether that be between teachers, between admin and teachers or between the association with the District.”

Board President Chris Norwood recalls first meeting Orlando while on the 2014 campaign trail at Peet’s Coffee in Milpitas. “Her passion and care for MUSD teachers, staff, students and families was evident throughout the conversation,” he recalled. “She wears her heart on her sleeve and is unapologetic about it. Fast forward nine years and numerous conversations later - her approach, care and passion are still very much the same. … She is always the champion for educators, friends and family.”

After remaining at Curtner for a year as a science specialist in 1990, Orlando transferred to teach 1st Grade at the same school and did so until 2000 when she moved to Pomeroy to teach 1st grade, where she remained until this school year’s end. “I looped between 1st and 2nd with my students until 4 years ago,” she shared. “I ended my teaching career in 2023 in second grade.”

“Leading from the heart, that’s what I’ve known Diana to do throughout her career. She is about people and strives for the best education for all learners,” said Superintendent Cheryl Jordan of her longtime MUSD colleague. “Diana has been an integral part of shaping our work together, especially in building a Culture of We; her love for kids reverberates throughout and will continue to do so for years to come.”

Colleague Laura Polden, now at Zanker Elementary, shared: “When I was a student teacher at Pomeroy, Diana always made me feel supported and loved. She is great for a warm hug and an ear to listen to everything you have going on in your life, not just at work.”

What has made MUSD so dear to her heart: “The people,” she said. “MUSD is my second family. I raised my girls in this District and I am proud of the education they received here. The lifelong friendships mean everything to me.”
Colleague Ashley Grilli, currently at Rose Elementary who established a strong, lasting bond with Orlando and her family over the years, shared: “Whether the occasion was celebratory or full of grief, Diana has always shown me what it means to be a caring mother, a committed teacher, and a person who stands up for what she believes in.”

Orlando, an active member of the Milpitas Teachers Association who has held officer roles of site rep, negotiator, lead negotiator, vice president and eventually president, stepped outside the classroom and dedicated 2022-23 as the first full-time released MTA union president. She fondly remembers fun times at the Benevolent BBQs up at Ed Levin Park at the end of the school year as well as The Sharon Smith Unity picnics. “It brought us together to celebrate the school year and wish everyone a wonderful summer,” she noted.

Some more of her most memorable moments/events throughout her storied career are playing in a bowling league with her MUSD colleagues, other staff bonding events, including trips to horse races, hockey games, baseball games, football games, “and who can forget the Perotti staff bus trips. Lots of good times in MUSD over the years.”

In the upcoming years, Orlando plans to spend more time with her daughters and boyfriend, traveling and working out. She also is interested in volunteering with Mental Health and Suicide Prevention groups and substitute teaching “to get my kiddo-fill and see all my friends and colleagues.”

For the younger generation of educators, Orlando said: “Teaching isn’t just a job, it’s a career. Find your passion within teaching and follow it. Always remember the reason you became a teacher because that will keep you moving forward even in the toughest of times.”

“Make sure you find balance between work and home because this profession can consume your every waking moment,” she continued. “Be creative, be silly, be the person you wanted as a teacher and never forget our kiddos need us and we need them. Teaching is hard but it’s so rewarding. Stay strong and enjoy this magical career we call teaching.”

---