Meet Dr. Barbara Ostos

She calls it the longest shortest year of her life. Dr. Barbara Ostos was announced as Santa Catalina’s fifth head of school in June 2021, but her first official day on the job didn’t arrive until July 2022. For those 13 months in between, Barbara planned and prepped like never before. She talked regularly with school leaders as she sought to better understand Catalina and its needs, reached out to other new female heads of school to form a network of mutual support and learning, and prepared to move to California with her family—all while staying on top of her duties as an assistant head of school in Oregon.

In the midst of that high-pressure chaos, during a visit to Catalina in March, Barbara still found time to take off her boots and join a game of kickball with a group of third-graders. Relationships are a theme that runs through Barbara’s 20-plus-year career in education, and a value that guides her as she settles into the Catalina community—a community built on relationships. Her knack for centering the human connection was one of many qualities that made her a perfect candidate for Catalina. “Barbara had the experience and qualities we knew were essential for the new head of school,” says Carolyn Hartwell O’Brien ’74, a member of the board of trustees and head of the search committee. “What drew me to her personally was her warmth and intelligence, and her natural ability to connect with the students she met.”

By all accounts, Barbara embodies Santa Catalina’s mission. She says, “I’ve always felt a higher sense of responsibility for the people around me, my family, and the communities I’m part of. Serving in that capacity— helping us be the best versions of ourselves as individuals and as a collective—is something that I’m drawn to.”

Barbara was born in León, Guanajuato, Mexico, and grew up in San Diego, where she and her two siblings were raised by their mother and grandparents. Her mother, a real estate agent originally from Cuba, worked hard to put all three kids through private school. Barbara attended parochial schools from prekindergarten through grade 8. As a PreK student at Sacred Heart Coronado, she was allowed to join the first-grade classroom while she waited for her mom to pick her and her brother up from school. “I was excited to sit there quietly and behave well, which I could do,” Barbara recalls.

She transferred to Saint Rose of Lima School for grades 4-8, and in sixth grade got her first taste of leadership as the lower school representative in student government. She continued to serve in the student government in high school at Francis Parker School, which she attended on scholarship. As student body president, she helped orchestrate a Las Vegas-themed homecoming where an Elvis impersonator skydived onto the football field to crown the king and queen.

Barbara was an athlete at Francis Parker, playing volleyball, basketball, and softball. “I was a tri-sport benchwarmer,” she jokes. She was also passionate about French, and traveled to France as an exchange student during her senior year. She had a lot going for her when it came time to apply to college, but it was uncharted territory. Her brother joined the Marines out of high school, which meant Barbara would be the first in her immediate family to go to college. She cast her net far and wide, earning acceptances from every school she applied to. She decided on Harvard University, where she was involved in Latino leadership organizations and worked in the admissions office. “Harvard opened my eyes to a larger world,” she says.

After graduating cum laude with a degree in government, and unsure of her next step, she learned that Francis Parker was looking for a history teacher, so she applied. During her interview, the head of school gave her some professional advice: “If you’re not going to be in a school for the rest of your life, don’t stay here for more than three years.”

It took her less than one year to realize that yes, this is what she wanted to do for the rest of her life.

“School is my jam,” Barbara says. “I get to work with amazing children, get to work with committed adults, get to think about what they need in the moment and what they need in the future—which is constantly evolving—and I get to work with families who are highly invested. What is there not to love about this?”

Barbara taught history, French, Spanish, and study skills in the middle and upper schools. She started taking on grade-level leadership positions and eventually became dean of students for the middle school. Turns out that middle school is also her jam. “The opportunity to mold and cheerlead and be patient and loving during those years is fun,” she says. “They still love doing silly things, but at the same time you can begin to really challenge them to think deeply.”

After 10 years at Francis Parker, Barbara moved to Portland, Oregon, to serve as the middle school head at another coed prekindergarden–grade 12 day school, Catlin Gabel. She held that position for seven years before being promoted to assistant head of school, and stayed there until coming to Catalina. During her tenure at both schools, Barbara continued her own education, earning a master’s degree in nonprofit leadership and management from the University of San Diego and a doctorate in educational leadership from UC San Diego.

When Santa Catalina launched its search for someone to take over after Meg Bradley retired as head of school, Barbara was casually looking for other opportunities. Wanda Holland Greene, head of the all-girls Hamlin School in San Francisco and a close friend of Barbara’s, provided her name to the search committee. The two met in 2014 when Barbara was accepted as a fellow in the Aspiring Heads Fellowship Program through the National Association of Independent Schools; Wanda served as her mentor. “Barbara’s intellectual heft, warmth, humor, and vivacity drew me to her immediately,” Wanda says. “I knew that Santa Catalina would be a place where Barbara could be her authentic self—both as a person and a professional. There was no doubt in my mind that her devotion to her Catholic faith and her own family, as well as her relentless focus on excellence in education, would be embraced at Santa Catalina.”

The more Barbara learned about Catalina, the more she saw her skill set and beliefs aligned with the school. Many aspects of Catalina caught her attention, from its Dominican history to the intention behind curriculum to the integration of a health and wellness program. She also values that Santa Catalina is a faith-based school. “I believe that a grounding in spirituality is an important part of raising healthy kids today,” Barbara says. “Research tells us that children who have a stronger spiritual base are less prone to anxiety and depression and further mental health challenges. Ensuring that they know they are loved and respected and valued, not only with each other and within our community but with something that’s bigger than them—I think that’s important.”

Ultimately, Barbara was drawn in by the conversations she had with students, teachers, parents, and others connected to the school during the interview process. Now that she’s here, she has made it a top priority to continue those conversations. She spent the first months of her term getting involved in student life and holding formal and informal conversations with constituents to hear about their experiences and ideas for improving the school. “This is about really getting to know people and allowing them to get to know me,” she says.

Listening and learning is the first of three major goals that Barbara has set for her first year. Her second goal is to assess institutional readiness for future initiatives involving diversity, equity, and inclusion. She brings experience to this arena, having led DEI initiatives at both of her previous schools. This year, she wants to start with collecting data to identify trends across all areas of Santa Catalina. Her third goal is to partner with the Upper School admissions team on creating an updated enrollment and retention plan.

“Working with Barbara has been invigorating and inspiring,” says Laura Lyon ’81, chair of the board of trustees. “Barbara is a natural when it comes to collegiality, encouraging others, and being truly authentic in her connection and care of those around her. Combine those skills with her professional expertise and seemingly boundless energy, and you’ve got in her what it takes to guide us forward in a bold and courageous manner.”

As a leader, Barbara loves to think about bigger problems and how to solve them, always in collaboration with others. She actively seeks alternate perspectives—even opposing ones—to help her make the most informed decisions. And she’s a doer. At one point during her conversation with the Bulletin she used the word hope when talking about the future of Catalina and abruptly stopped herself. “Not hope,” she said. “Hope is not an action. My goal is …”

Barbara is also not afraid to ask questions and to seek the right people to guide her through unfamiliar territory. As someone who worked in coed day schools for her entire career, she would be the first to tell you that leading an all-girls boarding program is an opportunity for growth. “Now that I’m here, I’m beginning to discern more clearly the areas where my experience and my competence hold me in good stead, and other areas where I can say, I don’t know,” she says. “For instance, all-girls boarding is absolutely one of those learning curves, so I’m actively reaching out to my network of mentors to get the support that I need.”

The rest is lived experience, and Barbara is getting plenty of that as she and her family settle into campus life. Her husband, Carlos, is a Venezuelan-born corporate accountant. Their children, Lydia, in seventh grade, and Luke, in first grade, are excited to be Santa Catalina Cougars. “The Ostos family is loving being part of this very intentional community,” Barbara says. “We have felt extremely welcomed by families and colleagues, and with Sister Claire and Sister Christine, it really feels like a homecoming of sorts.”

As she gets ready to tackle the second half of her first year, Barbara is looking forward to further building those all-important relationships and planning for the future of Santa Catalina School. “This place is amazing and has the foundation to forge forward in creative and relevant ways.”