After graduating high school, O'Brien packed his bags and left to launch a career in Los Angeles, doing a little bit of everything from working as a director's assistant to publicity for feature films.
"It just wasn't as fulfilling as I thought it'd be, even though it was what I always wanted to do," O'Brien said. "I decided I needed to have something more fulfilling in my life."
Looking back on his trajectory, O'Brien called his segue into the classroom "natural," especially coming from a family with a history of teaching, dating back to his great-grandfather.
"I always enjoyed school as a student and always had some amazing teachers that made a difference in terms of sparking my interest in school and different subjects," he said. "I knew I was going to go to college, so I always had a career path in continuing my own personal education."
O'Brien first considered teaching as a career during college when he was working at a sleep-away camp in New Hampshire.
"I really enjoyed working with kids and influencing them and getting to know them and always thought teaching would be a real natural career for me because of my personality and my way of working with kids. I always put that on the back shelf as another possibility," O'Brien said.
A few years later, O'Brien was participating in a company-wide volunteer day while working for Paramount Pictures that rekindled his dormant interest in education. "Working with the kids in the classroom, donating my time, I realized I really enjoyed it much more than what I was doing," he added.
O'Brien made a decision to completely stop his career in television and film and came back to the Bay Area to get his teaching credential from Dominican College in San Rafael. He then applied to teaching positions with a number of school districts, but PUSD wasn't one of them.
"The funniest part is I personally didn't apply to Pleasanton," O'Brien said. "I was living with my grandmother in the city and taking care of her while I went back to school ... and when it came time to apply to positions, it was the old send in the mail, it wasn't electronic.
"I was getting ready to go to the post office with about eight applications and noticed that day was the due day for Pleasanton Unified and so I thought if I mailed it, it's not going to get there in time, so I purposely didn't mail that one, I left it on the kitchen table," he continued.
"My grandmother thought I'd dropped it and she put a stamp on it and gave it to the mailman, so it was out of sight, out of mind for me. When Pleasanton called me up for a job interview, I said, 'I didn't apply to you guys,' and they said, 'Well, we have your information right here so come on in for an interview,' and the rest was history -- so I owe that to my grandmother."
Since then, O'Brien has been a popular teacher and administrator during 21 years with the district, including five years teaching at Donlon Elementary and another 12 years in the classroom at Hearst Elementary.
He said he enjoyed the past four years at Pleasanton Middle, but likes his new school because "there's fewer students so I feel like I could almost focus more on the elementary kids."
O'Brien envisions creating "a place where kids are learning but that they love to come here to learn," but he also has another all-encompassing goal for the campus.
"You could say a goal like we're going to improve 5% more on the state test scores -- what does that really mean other than we're teaching kids as best we can," he said. "It has to be deeper than that -- are we reaching all the needs of our kids? Socially, emotionally, academically, behaviorally. The main goal is to focus on all those things collectively."
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