Reflections On 2019--Circling Up

For many this time of year is filled with celebration and resolutions--and yet the milestone of a new year is simply a construct we have created. What remains clear, however, is how effective such a cycle of change can be for people. We operate well when there are beginnings and endings. 

It has always been my practice to use this time of year as reflection. Among the many things that Outward Bound taught me is the "ebb and flow cycle of experience"--this is what I now call Expeditionary Leadership.

It begins with a determined amount of time--the expedition. Prior to launch you plan. You meet with your partner and your course director and plan your route. You plan your meals and figure out what gear you will need. You discuss your strengths and places where you struggle. You review the files of the participants who will be joining you. And you lay out the first 72 hours.

Then you launch. During that immersive/training phase you are teaching. Much of the teaching revolves around the basic skills the group needs to survive--how to cook, how to set up shelter, how to read a map and compass. How to do whatever activity propels the group--paddling or backpacking or sailing or skiing. But the most critical teaching is around how to be in a small, intimate community--how to create a shared set of principles to live together, how to start and end the day, how to support each other when things get hard, how to have healthy conversations when conflict arises. 

As the journey progresses the Expeditionary Leader's role shifts, to one of coach. There is constant reinforcement for individuals to depend on each other and not the Outward Bound Leader. And finally, during the final expedition, the role of the Outward Bound leader is one of a safety net and a champion. If you have done your job well the group no longer needs you.

Reflection is built into this entire process. Guided journaling, debriefs of experiences and situations, and review of each day are the norm. We "circle up" to start and end any shared learning experience and the leader takes the crew through a process of reflection and learning.Talented leaders help make connections between the wilderness experience and each participant's life at home--we call this transference. Without reflection it's just a hard, maybe fun trip in the wilds. With transference it can become a life changing experience. 

This reflective practice has served me long beyond my days leading wilderness trips. And setting these "expeditions" has always allowed me to create beginnings and endings, specific points to reflect on what I have learned and where to course correct. In truth this is no different than establishing learning points in project management or using Scrum and Sprints in Agile. As a former Outward Bound leader who has had a career teaching Agile shared with me, "I've spent my whole life teaching people how to circle up."

So I reflect on 2019 and the conclusion of this annual expedition: I began the year visiting my publisher, Berrett-Koehler in Oakland and ten months later achieved a life goal of seeing my first book in publication. After that visit our family flew to Hawaii to explore a possible relocation. And here at the end of the year I sit in my new home in the town of Waimea on the Big Island. Along the journey there were good-byes--to my friends and colleagues in New Hampshire--and hellos, to new neighbors in Hawaii and new connections during the launch of my book. I travelled and connected and reconnected with amazing people who hosted me and celebrated the launch of my book with me. It was one of the most remarkable years of my life.

There were definite moments of doubt and fear and challenge in 2019. But looking back the path forward seems so clear. No matter what path you take in life you end up right in the moment of now. And for me, that moment leaves me with a deep sense of peace, gratitude and joy. 

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