Been there, done that.

Been there, done that.

“I said a bad word.” I murmured in a childlike voice. It was all I could come up with as they stared at us from below and offered supportive shout outs. I had just screamed a one-word profanity, as Will Laughlin and I, together, fell from the high wire. Dangling by the ropes, harnesses and the trust of our belays on the ground, I felt failure. Swearing was a fear and anger-fueled reaction. Instinctively, I flung one arm back and caught hold of the wire. We recovered and Will and I were once again upright grasping forearms and locking eye contact as if both our lives depended on it. We each leaned back, found the sweet spot where we could counterbalance the inequity of our size and weight and successfully sidestep our way to the tree.

I was leading the ISANNE Sparking Leaders retreat. During the group debrief I shared that the challenge had rattled me. I have done ropes courses before, lots of times, hell I have even taught them. I had the cocky been there, done that attitude. But then I fell. I failed. I hadn’t expected to. The richness in it though is that it was that I had to figure it out. I had to get back on the wire, synchronize with my partner, and get to the tree. I was experiencing the Outward Bound moto in practice: learn by doing. I loved it and was thankful that the ISANNE Sparking Leaders Retreat participants warmly invited me to actively participate.

As the new Director of Education and Innovation at Hurricane Island Outward Bound School I am humbled and honored by the responsibility entrusted in me and excited to be connecting with ISANNE as an early partner. With a background in Public Health Education and as a three-time Outward Bound alum, I feel I have finally found my place, my people and my purpose. Outward Bound believes in teaching the intangibles of character, compassion, courage, and confidence. I am charged with a worthy and significant role of advancing our educational approach and our impact. With faith in the OB philosophy and practice I decided designing a retreat for independent school leaders seemed like a great place to begin. Let’s involve education experts and see if what we are doing resonates with them, I thought. My inner sceptic questioned though, what outcomes is this group really after and how will I know if we made an impact?

Despite the thoughtful planning and program designing I had done with my Outward Bound team for ISANNE Sparking Leaders Retreat, I was new enough to lack confidence in our ability to really “spark” these leaders. After all, they too are experienced educators focused on social and emotional learning. I had to trust though that the retreat team-building exercises and the physical elements would prove both relevant and necessary to connect and engage the cohort of colleagues and peers with meaning and purpose.

Participants were leadership teams from Brewster Academy and The Oliverian School. Some activities were segregated by school, others were in a large group and occasionally individual. At one point, I was relying on a mix of three participants with a map and compass tromping through the woods in the dark. We all showed some vulnerability, felt a little uncomfortable and demonstrated some grit. I was inspired by the willingness everyone showed in trying new approaches to tackling problems. I noticed frequent shifts in group dynamics that allowed space for new leadership to emerge. Team members took turns with difficult tasks and supported one another’s “challenge by choice” decisions. A space was created where rapid self-awareness surfaced, and participants freely admitted when they could have done something better or more effective.

The reflection time was powerful. Teams shared how the retreat impacted them and their plans for transference of learnings back on campus. They felt better equipped to communicate and tackle challenges at school because they intentionally cultivated group dynamics routed in empathy, patience, and introspection. Insights turned into action plans.

Leaders unplugged, dove in and the sparks did ignite. Through a blend of observing, listening and participating in the two day retreat I didn’t just notice and self-discoveries, I felt them. As Craig Gemmell put it “Problem solving is play for us.” His team has made a commitment to playing with OB again.

We are all doing the same good work. Let us lean into each other – this deep network of talent and experience – to better understand our collective strengths, styles and even gaps. Join us for the 2nd Annual Sparking Leadership Retreat in June of 2020 where we will once again offer the option of participating in the CliftonStrength assessment as a complement to the wilderness retreat. 

For a deeper dive I invite you to also consider the exclusive Outward Bound sailing expedition in the Florida Keys designed specifically for educators or campus influencers.

I welcome this community into ours. It just makes sense. In the spirit of Outward Bound, let us learn together by doing together.

To those in the field,


About The Author

Amy Root

Amy Root is the Director of Education and Innovation for Hurricaine Island Outward Bound School and is based out of Camden, ME. She has been with HIOBS since 2019.