"There are so many beautiful things happening right now," read Jordan Fowler, senior class president of the Palo Alto girls' school, sharing the words of motivational speaker Steve Maraboli.
Fowler set the tone for a ceremony centered on the bonds formed in the Castilleja community and the strength and confidence the graduates have gained through those relationships.
After the senior class sang "In My Life" by The Beatles, class valedictorian Angela Li spoke of this confidence, telling a story in which she found herself at the top of a wooden pole, 40 feet off the ground, after she had climbed it at the encouragement from her friends during a sophomore retreat.
Upon jumping from the top of the pole, Li said that during her freefall, before the harness caught her, she felt "exhilaration" even though she was afraid of heights.
"I realized that it was true what people said. Life begins at the end of your comfort zone," Li explained.
"Both within and outside the classroom, we've been empowered to stretch ourselves to simply try out what we may not be initially comfortable with," she said.
Li spoke of the school's challenging assignments that pushed her and her classmates' boundaries. She said that throughout their years at Castilleja, Li and her peers implemented changes at the school, initiating projects and starting new clubs.
"But we would not be where we are here without the support of the entire Castilleja community," she said. "We had the help of our teachers and mentors who not only shared their knowledge but nurtured our lifelong love for learning."
Li added that she hoped that, upon graduation, her peers would continue to have "the strength and courage to take that flying leap."
"I cannot wait to see where we all land," Li said.
Guest speaker Mona Simpson, a UCLA English professor and author, said that during her high school graduation she felt average and "undistinguished."
"I knew I could have worked harder," she said. "I wasn't as good a student as I might have been, and I understood that, though I couldn't have said then exactly why."
Although Simpson said she had a difficult time remembering the details of her own graduation, she told graduates, in a speech peppered with humor, "This is the second huge rite of passage in your life, and you don't remember the first one."
On a more somber note, Simpson told the graduates: "Graduating high school is a big deal (because it is) one of life's plot points, and like most of those, it involves gains and losses."
Simpson shared her own coming-of-age story in which she navigated having a mother with mental illness, financial limitations and trial and error in her own writing before she became the student she never was.
"I was in the middle of a story I didn't understand," she said.
Although Simpson worked hard in college, she was driven by her passion for learning and not the promise of reward, she said. She cautioned graduates against focusing on their goals without taking their journey, and whether their needs are being met, into account.
"Don't worry about winning prizes or coming in first. Find love and community," she said.
"Most of all, to end by quoting Henry James, 'Live, live, live,'" she declared, her words followed by thunderous applause.
In the final speech of the day, Head of School Nanci Kauffman related the lives of the Castilleja graduates to the subject of "Lean In," a book written by Facebook's chief operating officer, Sheryl Sandberg.
"Published in the year of your graduation, Lean In is destined to become a symbol of this moment in time when once again discussions about the role of women and the choices we make have taken center stage," Kauffman said.
Kauffman spoke of Castilleja's motto, "Women learning, women leading," and said that the all of the graduates can be considered leaders.
She said that the graduates, who at one point or another shared their own perspectives, became leaders because they had to take a risk.
"I see our newest alums, young women who are poised to 'lean in,' even when they are criticized or misunderstood," she said.
Kauffman added: "Today you become Castilleja women forever. Honor this privilege. 'Lean in' to discomfort and make this world a better place."
This year, three of the "Castilleja women" — Grace Arnold, Simone Seiver and Amanda Stephens — shared the honor of the Castilleja Award, which is given, through a faculty vote, to students who exemplify what the school calls the "Five Cs: Conscience, Courtesy, Character, Courage and Charity."
Seiver, who is student body president, advised her classmates in an earlier speech to "use humor as a compass."
"Humor illuminates what is human. It's disarming. All the things in this world that can make you unfeeling — being too serious, too automatic, too pompous — humor is the antithesis to that," she said.
After the ceremony, Seiver, who plans to attend Yale in the fall and hopes to study an interdisciplinary major that combines ethics, politics and economics, said she did use humor to guide her in her college choice because she enjoyed the wit of the students she met when she visited the university.
At the same time, Seiver spoke with a sense of gravity as she recognized the bittersweet transition from high school to college.
"I'm thrilled, I mean, I'm on the precipice of a really exciting time, and I think my classmates feel similarly, that it's a combination of sadness and nostalgia but also a lot of joy and pleasure for what's to come."