In his Commencement Address to the Class of 2025, Head of School Bill Taylor reflected on the journey of the Class of 2025 through the lens of “becoming” — a process, he explained, marked by a deepening sense of self-awareness: “The awareness of who they are becoming… the awareness of what are their distinctive gifts and talents… the awareness of what distinguished each of them as human beings… and the awareness of the men they are becoming.” Building on that idea, he introduced the central theme of his address: vigilance. He defined it as “that sense of being alert, of being aware of what is going on around you and the opportunities that we are presented with if we are being alert to our surroundings.”
He explained that vigilance doesn’t only arise in moments of danger. “More often, the opportunities to sharpen our vigilance happen when we feel at ease, when we are comfortable, and when we are just going with the flow.” He praised the Class of 2025 for how they had embodied this idea: “First of all, I need to let everyone know that the Class of 2025 is a great class… And, for me, and for others who are paying attention, it is your vigilance that helps make this class truly distinctive and, indeed, GREAT.”
To the class as a whole, Taylor extended his thanks for the ways they showed up throughout the year: through over 30 chapel talks on topics like awareness, community, attitude, commitment, and forgiveness; through their leadership in chapel and contributions to school spirit; and through the depth and intention of their Senior Independent Projects. “You have indeed been vigilant toward the recognition of the gifts and talents of your classmates and other students at this School.”
In closing, Taylor challenged the Class of 2025 to take their vigilance with them — and to anchor it in self-awareness and integrity. “Be watchful. Be aware. Know when you have to act. And, equally as important, know when you may be better off waiting before acting. All of this involves vigilance.” He concluded with a reminder of what had made the class great: “Your vigilance is shaped by your integrity,” he said. “Not only that, strive to ensure that your vigilance is also connected to the fabric of integrity and relationships that have helped nurture your journey of becoming at Trinity-Pawling.”