Stephen Gilbert will end his career with the Gilroy Unified
School District in June
Gilroy – Stephen Gilbert doesn’t exactly fit the stereotypical retiree. He’s 55, doesn’t have grandchildren yet and wants to travel to Antarctica.
But he and his wife had always planned on early retirement.
“Probably 20 years ago we decided if we could retire at 55 we would make that a priority,” he said.
And since the Gilberts are “savers,” have made numerous real estate investments, tend to pay double mortgages and don’t have looming credit card debt, their long-held aspiration has become a reality.
The Rucker Elementary School principal will finish up his career with the Gilroy Unified School District this June. He gave the district notice of his retirement in January, in order to give them enough time to find a replacement, he said.
Although Gilbert knew he wanted to retire early, teaching wasn’t his initial goal. The Milpitas resident kind of fell into education.
Gilbert graduated from University of California, San Diego, in 1973 with a bachelor’s in history. After college he spent 13 years working in various management positions at Longs Drugs stores in the San Jose area. And from 1986 to 1988 he sold a melange of products to drug and grocery stores.
But he grew tired of retail and was looking for a career change. At a party he met an employee from the Milpitas Unified School District who suggested that he substitute teach.
One day in the classroom and the Rucker principal knew he’d found his niche.
“The first day I came home I was hooked,” he said.
Gilbert decided he liked the elementary school age the best and began teaching in the Hayward Unified School District. He taught in Milpitas for five years before making the move to the administrative sector.
In 1997, he was hired as assistant principal at Las Animas Elementary School and moved up to principal two months into his tenure when the principal resigned. Four years ago he took over as principal at Rucker, Gilroy’s north end elementary school.
Cindi Heath said her first experience with Gilbert when her daughter was in the second grade was pleasant.
“He was very helpful,” she said. “There was an issue that needed to be addressed and he listened to what I had to say.”
Two of Heath’s three children attended Rucker when Gilbert was serving as principal. Heath said Gilbert attended all of their meetings, was supportive and was always the last one to leave at events.
“I think he did what he felt was in the best interest of the school and the children,” she said.
Gilbert decided to make the transition from teaching to the principal’s office because “I was looking for a way to have an impact on a larger number of kids and a different level of challenge.” And because of his managerial background in retail, Gilbert knew he would fare perfectly well as a supervisor.
So what will the Santa Cruz native miss once he enters the world of retirement?
Gilbert will miss being involved in the decision-making process and the unique diversity of Rucker, a school that’s populated with migrant students, students who transfer specifically for the GATE program and wealthy kids living on big spreads in the country.
But the one segment of his job he thinks he’ll miss when he ends his tenure at Rucker, is the unique relationships he’s developed with the school’s 500 students and parents.
Although they won’t be Rucker kids, Gilbert will have a chance to develop those bonds during retirement. For the next couple of years, the former educator plans to return to the classroom to teach, but it won’t be in Gilroy.
After spending an average of two hours a day commuting, he wants something closer to home. Gilbert’s excited to apply all the strategies he’s learned, such as those to help students learning English, since beginning his tenure as principal. Back when he was teaching, everything wasn’t so data-driven and individual student assessments weren’t “as pervasive.”
That attentiveness to achievement and raw information is one of the characteristics Amy Anderson highlighted when asked about her boss.
“He’s very organized and he’s very good at crunching numbers,” said the fourth grade teacher, who has taught at Rucker for eight years. “He keeps us focused on data and data analysis.”
Gilbert Profile
Education
– Bachelor’s:
UC, San Diego
– Teaching
credential: San Jose State
University
– Master’s:
CSU, Hayward
– Professional Administrative
Services
Credential: SJSU
Family
– Married, 32 years
– Daughter, 24
