Sailing100Simon Peter first met Christ on the shores of the Sea of Galilee, a story we hear in the fifth chapter of the Book of Luke. During a single morning, Peter changed the direction of his life, choosing to stop being a fisherman in order to follow Jesus and become a “fisher of men.” Peter’s story was apt for explaining a phrase that I use: “more sailing than driving.” I have made a habit over the last couple of years of describing any situation that will require finesse and an ability to adjust on the fly as “more sailing than driving.” For some reason, almost certainly misguided, I have assumed everyone knows what I mean. In short, Simon Peter made a life decision like a sailor does. He was not following a specific roadmap. He was faced with something he could never have expected that offered a life of greater meaning. So, just as a sailor does when facing a new opportunity, he chose a new course. His ability to do this represents courage and boldness. Already a proven leader, he chose to follow.

As a young girl, my mother grew up sailing each weekend on Fishing Bay around a point from the far larger Chesapeake Bay of Virginia and Maryland. Years later when she tried to pass along her love for sailing to my sister and me, it was clear early on I would not be much of a sailor. At age six or seven, my contribution was to complain about being bored and do my best to avoid being hit in the head by the boom swinging across when we tacked. I liked going fast, but we rarely seemed to go fast. In the moments when the wind faded to a breeze, then diminished to stillness, I wondered why we’d chosen floating in a hot boat rather than some other more entertaining hobby such as capturing bugs on the grassy edge of the narrow bay shoreline or fishing for sharp toothed Blues. During those dead air moments, as we sat waiting for any breeze that might help us move again, I realized that sailors never go straight toward their destination. They take advantage of what the wind gives them—moving closer to but not directly at their destination with each tack. Good sailors know how to make the most of the situation, and they know how to take advantage of an unexpected opportunity—a breeze stiffening off the port bow or the promise of an advantageous wind around the point. With decades (and decades) separating me from my time at Fishing Bay, I have come to see sailing metaphorically, rather than simply as a pastime I never quite understood well enough to see why some people thought it was fun.

Long after my time on Fishing Bay, I watched the America’s Cup with fascination for two central reasons. First, were the moments when two boats would take hugely different routes to the same buoy—there was something ingenious about the strategies of the skippers. Second, sailors on those boats knew exactly how to work together toward a greater goal. The defining characteristic of the best boats was the ability of a crew to be stronger because of each other, rather than trying to find success despite each other, or trying to be better than one another. Our graduates when we have done our work well, learn to be part of such crews, and they learn to be skippers of such boats. Peter was clearly able to fulfill both jobs—we and the young people in our charge can do the same, and importantly, all of us should.

All too often we pretend there is an accurate roadmap for what lies ahead of us in our lives—a sequence of turns along a well-delineated route guaranteed to take us where we need to go. A lot of schools appear to teach their students as if this is true. Implicitly or explicitly they, in partnership with parents and families, send the message that a young person should go here [insert name of college], major in X [insert major], get a job doing Y [insert profession], and live here [insert name of city]. This is dangerously misleading, and it sells our young people far short. The best-laid plans fall away when we are faced with the unexpected. In such moments, we want our kids to be equipped like Peter to navigate a new opportunity and challenge. I want our students to be ready to rise just such an occasion. In an Episcopal school such as ours, this is our most important and I believe, sacred work.

So, what should we want our students to learn? To sail. Our students should become good sailors—entrepreneurial ones, ones who are brave enough, as well as smart and knowledgeable enough, to make a necessary shift in order to work toward a better world, a more fulfilling life—ones who, like Peter, know how to become part of something greater than they may have ever imagined.

Earlier this year, my wife, daughter and I headed to Richmond, Virginia to help celebrate my mother’s eightieth birthday. In the piece above I mention my mother as a sailor who spent much of her youth on the water pulling everything from the wind it would give her. To my thinking now looking back over so many years, she was a sailor the way a good musician is a musician–at some point such people forget the science, and they move on by feel. On the water she learned to trust herself, as well as work with others; she learned to be brave enough to ride on the full strength of a powerful tail wind, as well as patient enough to sit out still air. My mother has needed all that learning in her life, and she has deployed it in a way that has showed me to aspire to as much myself. Her intelligence, grace, kindness, humility, passion, work ethic, and even her “don’t tread on me” approach to multiple cancer battles together serve as an excellent buoy for which any of us might rightly sail.

About the Author

Ross Peters 200wJ. Ross Peters serves as Head of St. George’s Independent School in Memphis, Tennessee. Before coming to St. George’s, he was Head of Upper School at The Westminster Schools in Atlanta, Georgia. He has also served as Upper School Director at Hawken School in Cleveland, Ohio and as Assistant Head for Academic Affairs at Asheville School in Asheville, North Carolina. He holds a B.A. from The University of the South and an M.Ed. from the University of Georgia. Read more on Ross’ blog at