Q&A with Greg Rolland, VISIONS Leader Alum

Greg was a leader on our first Alaska cross-cultural summer service program in 1995.
He looks back on the early days and what those years meant to him.

What years did you work with VISIONS and on what programs?

“VISIONS was a pioneer in cross-cultural service programs for high school students” . I was part of the inaugural VISIONS Alaska (a now retired) program in Gulkana in 1995 with director Bradley Hubbard, Susan Kolb, John Freeman and his wife/partner Lisa Olszewski, and Zak Barse. I spent three summers leading programs in Alaska, returning in 1996 (Gulkana) and 1997 (Mentasta). I then returned as Program Director for the 1999 South Carolina Sea Islands program among the Gullah culture of John’s Island.

What made you want to be a leader for VISIONS?

It just sounded so amazing to share my love of outdoors and cross-cultural service learning with volunteer teenagers and when I spoke to legendary founder Joanne Pinaire on the phone, I was sold on her passion and integrity. As a teenager, I had explored the Beartooth Mountains of Montana on a backpacking trip with Outward Bound, and expected to land at one of the Montana programs. But Joanne took a chance on me for that first Alaska summer and I’ll always be grateful.

Tell us about your experience during your VISIONS program.

We did many cool construction projects for our host communities: Sheds and building additions made from wood and cinder block; playgrounds; a basketball court; and even a timber bridge over a stream.

But the most transcendent moments came from nature and the warmth of our hosts: Being invited to a seasonal hunting camp with fresh-cooked Copper River salmon, ATVs pulled by sled dogs in off-season training, the sightings of moose and Dall sheep, the 360 degree views atop a mountain summit. All of it without selfie sticks, cell phones, or electronic devices (well, maybe a satellite phone—we can’t be perfect)!

What did your VISIONS experience mean to you?

Look, we’re all on a journey in life and I am definitely the “seeking” type—I wanted to explore, learn, connect, and make sense of a complex and multicultural world. Leading VISIONS was transformative and utterly joyful—which for a pretty serious, intellectual guy, that’s saying something! We all worked hard while also having opportunities to play, listen, and take interpersonal risks. My VISIONS experiences gave me a more optimistic view on humankind—they affirmed that it’s possible to create a positive and trusting community of people within a short period of time, and even across cultures.

What have you done since, as a throughline to that experience? How did your work with VISIONS influence the work you are doing now?

Well for one, VISIONS offered such meaningful experiences that it was very hard for me to break from leading summer programs! But eventually I transitioned to overseeing on-site wildlife classes and summer camps for kids at the Baltimore Zoo (now called the Maryland Zoo). It was a time of changing leadership and poor management choices there, and employee trust deteriorated to the point that the zookeepers unionized.

Let me tell you, it’s hard to sit comfortably with dysfunction when you have experienced teamwork and good leadership like I had at VISIONS, so ironically, that period propelled me in a new direction: I headed off to graduate school with a focus on nonprofit management, eventually focusing on finance and accounting. Now I work in school administration at an independent boarding school for teenagers.

What kinds of things did you take away from your VISIONS experience (intangibles)?

Before VISIONS I was a service-oriented athlete, poet, visual artist, and intellectual. But afterwards I walked away with greater self-confidence and an awareness of myself as a leader, despite leaning toward introversion.

Also I really treasured the regular Circle, or group meetings, when we took deliberate time to pause, reflect, and really listen to everyone on the program—what an opportunity to foster empathy, empowerment, and healing! In my professional life today, I shamelessly borrow the lessons of VISIONS and build in moments for regular group sharing and listening among my office team.

What are you up to these days?

I live in Massachusetts along the Connecticut River valley with my wife and we both work at a private boarding school, me in school administration handling the finances (I am a CPA now) and my wife as nurse director for the health center. I like trail running and just got back from a favorite 5-mile loop on the mountain ridge nearby.

Not long ago I reunited with Josh Block, a friend, teacher, and former VISIONS leader, to hike the demanding-yet-breathtaking “Pemi Loop” in the White Mountains of New Hampshire. But mainly I’m just trying to appreciate time with my teenage daughters before they all head off to college and beyond.

We hear you’re sending your child on a VISIONS program this summer! What helped influence that decision?

Haha, it never was my call actually. I’m happy to say that VISIONS was her decision alone, and based on the live webinar she attended. If you’ve been a parent long enough you might relate: To a teenager, what a parent did a generation ago usually carries little weight or perceived relevance. But I’m secretly very excited!

What do you hope to be doing 10 years from now?

So much! Another chapter of life. Another adventure. There is paid work in this world and there is the compelling work that desperately needs to be done. Sometimes they overlap but I am hoping to lean into the latter as much as possible.

What would you like to say to the VISIONS community?

These are tough times. Cherish the fact that you were and still are a part of something special. Be gentle with yourself and others. Thanks for doing great things and being an inspiration!

Anything else to add?


Owen Clarke is a writer for VISIONS. A career outdoor journalist, his work appears in 30+ international magazines, including Iron & Air, Climbing, Outside, Rock and Ice, SKI, Trail Runner and The Outdoor Journal. He is also the executive editor of Skydiving Source and Indoor Skydiving Source.

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