Headmaster Bill Taylor in All Saints' Chapel

As an educational leader, I find myself looking forward a good deal of the time. What skills will students need to possess in the future in order to be well-prepared for a changing world and a dynamic workplace? What will be the short and long-term implications of the pandemic on student learning and well-being? What do we need to be doing now to ensure that Trinity-Pawling will be well-fortified to provide a transformational learning experience for its students five to ten years from now? How will we strategically augment the financial foundation of the School to ensure that it can weather another unforeseen storm in the future like we were able to do with the recent pandemic?

Indeed, much of my job is about looking forward, and then planning backward from that vision. When I tend to look backward in time, it is often to ensure that important traditions and successful strategies are not overlooked in the planning process for the future. As a result, it has always been difficult for me to look back solely for the purpose of reflection.

This month, Trinity-Pawling will undergo its decennial accreditation by the New York Association of Independent Schools (NYSAIS). This process includes a four-day visit to campus by educators from other New York State independent schools who have been tasked with the responsibility of confirming that the School is meeting certain standards for the present and has a plan in place to direct its momentum towards a sustainable future.

The faculty and staff of Trinity-Pawling School have spent the past year and a half preparing for this process through the creation of a comprehensive self-study of the School’s progress since the last accreditation in 2012. This self-study also points to the future that has been illuminated by our Strategic Vision that was adopted by the Board of Trustees in 2021.

In reading through the self-study report created by our team of faculty, I could not be more proud of where we are as a school. Much has been done over these past ten years to move the School forward: the curriculum has been enhanced to better leverage ways that boys learn best through experiential learning; the endowment has been significantly enhanced; and there has been the creation of new facilities and the renovation of older ones; among many other changes designed to strengthen the School and the experience of our students.

The self-study process revealed the many ways that the School has sought to lean into important traditions to bolster their relevance for the present and the future. The self-study points toward the future and illustrates how the School can continue to improve and grow stronger in ways that have been outlined in our Strategic Vision.

This self-study process also highlights the tremendous work that has been done by the faculty of Trinity-Pawling School over the past ten years. They are the driving force behind the School’s progress and the means by which the goals of our mission will be realized in the experience of our students. Significantly, though, it is the faculty that is the entity by which continuity from the past is brought to relevance as the School moves forward through its present and into its future.


by William W. Taylor