For Jason Smith '99, purpose has never been about a title—it has always been about people.
From the classrooms of The Woods Academy to the streets of Washington, D.C., and now the halls of St. John’s College High School, Jason’s life has been defined by a simple but powerful philosophy: invest in others, and everything else will follow.
A Foundation Built on Community
Jason’s memories of The Woods are filled with joy, friendship, and a deep sense of belonging.“I loved my experience there,” he reflects. “It was a great community—it was special.”
He recalls everything from performing in the Grade 8 play to time spent in the library, but what stands out most is the people. Surrounded by a close group of friends from across the globe—including Brazil, Zimbabwe, China, and Slovenia—along with the teachers who shaped him, Jason was deeply influenced by a community that celebrated both connection and diversity.
Among them, one educator stands above the rest.“Mrs. Piwko really challenged me and pushed me,” he says. “She never let me be comfortable, in the best way possible.”
That balance of care and accountability became a defining influence, shaping Jason’s approach to leadership for years to come.
Structure, Discipline, and a Calling to Serve
Jason credits The Woods with giving him something he needed early in life: structure.“I needed structure, and The Woods gave that to me,” he explains. “That discipline carried into high school, into the police department, and into my life.”
Originally aspiring to join the Secret Service, Jason took advice from a mentor and pursued law enforcement as a pathway. What began as a stepping stone quickly became a calling.
Over 12 years with the police department, he served throughout Washington, D.C., including Southeast and Southwest neighborhoods. His work ranged from patrol to specialized units focused on crime prevention, firearms removal, and undercover operations.
But for Jason, the most meaningful part of the job was never the assignments—it was the relationships.“The best part of the job was the people,” he says. Rather than staying behind the wheel, Jason and his partner chose to walk the streets, attend community events, and build trust.
“We had to become part of their lives,” he explains. “If you’re not investing in people, you’re not going to connect with them.”
A Life-Altering Turning Point
In 2018, Jason’s life took an unexpected turn. Diagnosed with a brain tumor, he underwent surgery that led to significant complications, including hearing loss and a stroke. What followed was a long and difficult recovery—learning to walk, see, and regain basic functions.
Yet even in that moment, Jason found clarity. “It was completely meant to be,” he reflects. The overwhelming support from his fellow officers and community reinforced what he had always believed: people matter most.
And as one chapter closed, another began.
Returning to Education and Purpose
After retiring from law enforcement, Jason felt a pull back to a familiar place: education.
Through a conversation (not even a formal interview) he found his way back to St. John’s College High School, where he now serves as Assistant Principal of Student Safety and Conduct. “The minute I started working with the kids, I knew it was what I wanted to do,” he says.
In his role, Jason oversees everything from campus safety systems to student discipline, but his approach is anything but transactional. Instead, it mirrors the same philosophy that guided him as a police officer: build relationships first. “I don’t want our office to be a place students are afraid of,” he explains. “I want it to be a place where they feel cared for.”
Leading with Accountability and Compassion
For Jason, leadership is rooted in a balance of accountability and care. “I want students to know that I care about them,” he says. “And because I care, I’m going to hold them accountable.”
Whether he’s helping a student navigate a difficult moment or simply showing up at games, plays, and events, Jason prioritizes presence. It’s in those everyday interactions that his impact is most deeply felt.
He recalls one student undergoing cancer treatment, quietly battling lymphoma while continuing to attend school. “I just wanted to make him smile,” Jason shares. “Sometimes it’s the small moments that matter most.”
Defining a Life of Purpose
When asked what it means to live a life of purpose, Jason’s answer is clear: “Putting others first.” It’s a philosophy that shows up in everything he does, from mentoring students to supporting colleagues to simply being present for those who need it most.
And it’s a lesson he hopes to pass on to the next generation. “Treat every interaction like it matters because it does,” he advises. “Leave people better than you found them.”
Full Circle
Today, Jason’s journey reflects the very values first nurtured at The Woods Academy: community, compassion, and purpose. “It’s one of those places you always come back to,” he says. “It’s hard not to look back and smile.”
From a student shaped by strong mentors to a leader shaping the lives of others, Jason Smith’s story is a testament to the enduring power of education and the profound impact of a life lived in service to others.