Winston Fisher '92: Building Community, Leading with Purpose

For Winston Fisher ’92, Sandy Spring Friends School was far more than a place to learn. It was a place where he felt accepted, challenged, and genuinely safe to be himself.

“It was the community,” Fisher reflects. “It was a group of people who were just accepting and a place where I could feel comfortable. That really made a difference. It embraced me.”

Today, Fisher’s life and career span business, philanthropy, and civic leadership. As a partner at Fisher Brothers, the renowned real estate development firm founded by his family, he has spent decades helping lead complex projects while also dedicating significant time to nonprofit and civic causes. But when he reflects on his years at SSFS, what stands out most is not achievement or prestige. It is the feeling of belonging that shaped him during some of his most formative years.

“It was still coming out of the hippie era,” he says with a laugh. “There was that vibe, but at the same time it was a place of rigorous academics.”

That balance of warmth and intellectual challenge left a lasting impression on him. Fisher recalls courses like English history and Russian literature as deeply influential, not simply because of the material itself, but because students were expected to engage thoughtfully and critically with the world around them.

“We had high expectations,” he says. “You had to prepare. You had to be engaged.”

More than three decades later, Fisher believes the kind of education he received at Sandy Spring is more relevant than ever.

“We live in the age of AI, where critical thinking is probably the most important skill you can have,” he says. “What’s more foundational than being taught ethics and critical thinking?”

Importantly, Fisher distinguishes safety from sameness. What mattered to him at Sandy Spring was not conformity, but the freedom to question, grow, and develop his own perspective within a community grounded in care and respect.

“I never felt constrained at Sandy Spring,” he says. “I felt it was a place where people were safe.”

That sense of openness continues to shape the way he approaches leadership and civic engagement today. Fisher describes a meaningful life not as one focused narrowly on success, but one rooted in participation, curiosity, and contribution.

“I want to live an interesting life,” he says. “A life where you’re engaged, you’re trying to help people. I like solving problems. Doing things that benefit society is rewarding.”

Throughout his career, that philosophy has guided both his professional work and his philanthropic involvement. He believes deeply in stepping forward, taking responsibility, and remaining engaged with the broader world.

“There’s no substitute for hard work,” he says. “Be the person who gets there earliest and stays the latest. Raise your hand and take responsibility.”

For current students and young alumni still finding their path, Fisher offers advice rooted in both humility and resilience.

“People think they have to have every answer early on, and you don’t,” he says. “You have to try things.”

And when obstacles inevitably arise?

“You dig under it, jump over it, go around it — but don’t stand there in front of it.”

As he reflects on the future of Sandy Spring Friends School, Fisher hopes the qualities that shaped his own experience continue to define the community for future generations: intellectual rigor, ethical inquiry, and a culture where students feel both supported and empowered to think for themselves.

“I hope it’s still a place where people feel safe to be themselves,” he says. “The schools that do a great job are the ones that teach people how to engage with differences and develop their own points of view.”

Looking back, Fisher sees SSFS not simply as a chapter in his life, but as part of the foundation beneath it; a place that helped shape his values, sharpen his thinking, and reinforce the importance of humanity, belonging, and courageous dialogue in an increasingly complicated world.