Articles

Antifragile Schools are Sailboats with Great Crews

Written by Ross Peters | September 17, 2026

For me, sailing offers an apt metaphor for the antifragility requisite to preserve and extend a healthy, strategic school culture.

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 the sharp toothed Bluefish that we called Choppers. During those dead air moments, as we waited 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 intended destination with each tack.

Strategically successful schools are like sailboats with an excellent crew. These antifragile schools have the ability not only to survive threats, but to gain strategic, competitive advantage as a result of how they meet opportunities.

Such schools have a stable sense of identity, one that is broadly shared and consistently communicated. The essential characteristic of an antifragile school is the ability to hold onto what is core to the identity and character of an institution, while also nurturing an ability to react to changes in the ecosystem in which the institution exists.

Institutional antifragility deepens when it approaches volatility, uncertainty, complexity, and ambiguity (VUCA), as a BOTH/AND challenge. Such schools are BOTH keenly aware of what to preserve at all costs AND willing to make changes, at times bold ones, in order to adjust to and flourish within a fast evolving operational and cultural context. Antifragility requires a deft balance between preservation and change, and among its critical outcomes is competitive advantage.

When institutions go astray in a VUCA environment, it is likely a result of tilting too far in one direction or the other. When the preservationists dominate, an institution may become particularly brittle and thus vulnerable to outside threats — they are simply not able to adjust to or respond to challenges with decisive and productive action. In EXPLO Elevate's work with schools on enrollment management, we see schools' inability to adapt time and time again. Such schools slip into a kind of dangerous paralysis and simply maintain the same failing steps over and over, year after year. While they avoid becoming victims to every new trend, they lose the chance to imagine new pathways to success.

On the other extreme, when the loud voices of dramatic change dominate, corrosion is likely to occur from within as some board members, teachers, and even leaders will press against what they perceive as a dangerous reaction to shifting conditions. In this situation, the tension is internal to the institution. As opposed to a challenge outside of the school to which the school must react, such as changing local enrollment market conditions, or a new competitor, or an economic downturn, the internal tension reveals itself through increasingly strident tensions finding their way to the surface of the school's strategic dialogue. The preservationists make too many things in the school sacred and untouchable, while the change-centric voices can be too willing to let go of critical components of the school's identity.

Therefore, in addition to preserving those aspects of a school's identity that should never change (a short list), stewarding equilibrium between stability/familiarity and change is therefore central to institutional antifragility.

In the context of stewarding school strategy, successful schools have the ability to "hold course" (preserve), as well as to "tack" and "come about" (make change) in order to get where they want to go without ever losing sight of what should never change or denying the need at times to alter approach. In other words, preservation and change exist in a symbiotic relationship with a shared goal rather than existing in a conflict between right and wrong where one side or the other will win. Each in equal parts shares in strategic success.

When the crew works in balance, the boat has the greatest chance to "win." Winning in the context of admissions and enrollment strategy, for instance, means achieving competitive advantage by yielding an abundance of great-fit students and retaining the highest possible percentage of them through graduation.

With decades separating me from my time at Fishing Bay, I have come to see sailing as more than simply a pastime I never quite understood well enough to see why some people thought it was fun. Good boats and accomplished crews, like successful institutions and the experienced leaders within them, know how to make the most of the situation, and importantly 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. Additionally, they know how to stay on course as the wind slackens or shifts. And not less significantly, they know how to read the wind so they don't spend too much time directly facing into the wind.

Too often we imagine that strategy is something that pretends to be an accurate roadmap for what lies ahead for an institution — a sequence of turns along a well-delineated route guaranteed to take us where we need to go. This is dangerously misleading. To believe that we are driving on a predictable path dramatically increases our vulnerability to the unforeseen circumstances that arrive for all institutions. Such roadmap-devoted leaders and institutions look great when things are going their way, when their strategy is right on schedule, when demand is high. However, when something goes off course, they become quickly ill-equipped to take decisive action. Sailing provides a far better way of understanding a healthy approach to strategy because it prepares us both for staying on course and for finding our way back on course when the context within which we operate changes. It gives us a way of navigating all the "points of sail."

Great Schools — ones prepared to excel in the years ahead — both preserve and change...and again...and again. They recognize that in order to end up where they want to go strategically, they must sail.

Such an approach defines institutional antifragility and sets a course for strategic execution and institutional sustainability.