Stephen Druggan, Head of School, Springside Chestnut Hill Academy

In an interview with Invest:, Stephen Druggan, Head of School at Springside Chestnut Hill Academy, discussed the institution’s commitment to nurturing student potential through relationships, real-world problem-solving, and holistic wellness. He emphasized preparing students for life beyond college by equipping them to navigate a digital world and lead with an entrepreneurial mindset. “Education is all about relationships,” said Druggan. “It’s not a certain lesson or algorithm or poem, but how someone made you feel as a student.”

What insights or practices from international education do you believe will be most valuable for students and families in Philadelphia?

I don’t think it really matters where you are in the world — education is about relationships. It’s not a specific lesson or algorithm, but how someone made you feel as a student.

At SCH, we blend historic traditions on our Philadelphia campus — some dating back to the late 1800s — with forward-thinking approaches. We ensure teachers and colleagues have the support they need to build relationships that help students reach their full potential.

We draw students from more than 100 zip codes, giving the school a village-like feel — a place the city comes to. Our campus welcomes students into a community where people genuinely care about them. That’s the core of education.

From your perspective, which key trends are shaping education today, and how do you see them influencing the future of your school?

If you’re an 8- to 15-year-old today, the algorithm is playing you. That wasn’t true when we were growing up. The question is whether we’re equipping students to understand how algorithms shape their lives — and to stay healthy and whole in a digital world that isn’t going away.

Second, as part of a privileged community, we ask how we can give back. Through our Center for Entrepreneurial Leadership, 100% of our students leave grade 10 having launched a venture — for-profit or nonprofit — centered on something they care about.

We emphasize caring for yourself so you can care for others. In a digital world, do we still understand the need for nature, for service, for community? Those village-school values, rooted in SCH’s history, matter more than ever.

Given your offerings in engineering, robotics, and outdoor education, which impacts do you see as most powerful on students’ growth and development?

The culture of this school is a culture of “yes.” Too often, schools operate from a culture of “no” — or from the idea that tradition dictates who students should become.

At SCH, we aim to develop students who see everything as an opportunity. Problems are opportunities. Success is an opportunity. When a student asks a question, the answer is “yes — and here’s how we can make it happen.”

That mindset begins early, with small classes and engaged teachers — on campus, in the woods, and through CEL — encouraging students to build, test, and explore. Students leave here comfortable pushing boundaries and taking intellectual risks.

I love that approach, because too often young people are conditioned to hear “no” as they’re shaped into compliant future workers.

For 20 years, our board chair was Dick Hain, founder of Urban Outfitters. He played a key role in guiding the merger of two traditional schools into a more contemporary, independent institution. That influence helped establish an ethos of learning from the past — but using that wisdom to make the world better, not simply the same.

Given that your curriculum emphasizes entrepreneurship, design, and real-world problem-solving, how does this prepare students for life beyond graduation?

In many ways, we’re more focused on preparing students for life at 25 and beyond than simply for ages 18 to 22. Yes, our students attend top colleges — but what matters is what they do with those opportunities.

Students are given a blank sheet of paper, along with mentors and structure, and asked to turn it into something meaningful — and to be accountable for it. That’s much closer to real life than filling in bubbles on a test.

Our goal is for students to leave not just comfortable with a blank page, but excited by it.

You mentioned the importance of being healthy and whole. What progress have you seen in wellness and belonging?

All middle and high school students participate in multiple sports — typically one they excel at and another where they learn to support others. Finding a physical activity you enjoy is key to lifelong health.

Equally important is the arts. Throughout history, the arts have helped people make sense of the world, especially in difficult times. Students are required to engage both physically and creatively, and to learn how those dimensions work together.

One challenge is helping students know when to take something off their plate. American culture struggles with “white space.” When you do too much, none of it tastes good — so we intentionally build in room to pause.

What role do you see technology and innovation playing in teaching and learning?

Technology has clear downsides, especially around social media — but also enormous potential. The challenge with AI is whether it makes students lazy or pushes them to think more deeply.

If AI simply helps students finish faster so they can disengage, we’ve missed the point. But if it’s used as one of many tools to grapple with complexity and make sense of the world, then it strengthens learning.

We write to understand a complicated world. The question is whether digital tools help students do that work — or avoid it.

As you look ahead, what are your top priorities for this next chapter of leadership?

My top priority over the next decade is organizational health. Over the past nine years, this school has accomplished an incredible amount. I don’t know exactly what the next 10 years will bring — but my responsibility is to ensure our teams are healthy, cohesive, and clear in their purpose.

We didn’t expect to run a school through COVID, yet we did — and we were the first in Philadelphia to reopen for in-person learning. If we maintain clarity, reinforce it, and communicate it well, I trust we’ll be ready for whatever comes next.