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Headmaster's Blog


Teaching in Transition, Discovery of Self

This is an unprecedented time to be a student. It is a remarkable time to be an educator. And, it is a somewhat disconcerting time to be a parent. The world is rapidly changing, and the social, economic, and demographic implications of this change are extraordinary. Our students are growing up in a world that will look much different when they enter adulthood than when their parents did. It is estimated that by the time a student today is 38 years old, he or she will have had 10-14 different jobs. If the trends from the past decade continue, the jobs that will be most in demand when today’s high school student enters the workforce did not exist when that student entered high school. At the same time, 15% of the school-age population that is educated in India represents a greater number than the entire United States workforce. While no one can accurately predict the future, it is prudent to anticipate that the pace of change that has defined the recent past will continue to shape the future.

What are the challenges for schools to prepare students for this future? In addition to creating a foundation of academic knowledge, it is incumbent upon schools to also strongly emphasize those skills that will be necessary in this rapidly changing world: critical thinking, collaborative leadership, creativity, entrepreneurship and initiative, written and oral communication, analysis, and problem solving. In a world characterized by the ubiquity of technology and automation, these skills are representative of what cannot be easily replicated. It is the goal of Trinity-Pawling to deliberately highlight these skills in the curriculum because they garner greater individualized value in college and career. None of these skills, however, will be useful, unless the student also develops a deep sense of self-awareness of their own gifts, talents, and potential. The critical job of the educator today, therefore, is to build the skills that will provide value for our students from a foundation of developing self-awareness and autonomy. I believe that Trinity-Pawling is distinctively and deliberately poised to prepare our students for an ever-changing world as leaders.

In a recent column in the New York Times, David Brooks wrote of the need for schools to help students channel their energy and focus toward emerging interests. His argument is that a learning culture driven by the prominence of the G.P.A. forces students to spread their energy and focus across a wide spectrum of areas, instead of challenging student interest toward an exploration of their passions. While schools today do not live in an “either-or” choice between emphasizing G.P.A. or individual student interests, I do believe that many schools do not do enough to help young people discover their gifts, talents, and passions. The learning environment at Trinity-Pawling guides students toward greater self-awareness through the relational trust that characterizes its community. Here, there is room for boys to explore interests and pursue passions in a learning environment that encourages healthy risks and supports them in this process.

In the newly developed Practicum for Civic Leadership, Trinity-Pawling students will be afforded the time and resources to explore their interests on a deeper level, strengthening their foundation of self-awareness. Each rising senior is asked to ponder and select an area of personal interest they would like to pursue further. The School will help channel this exploration and, ideally, team each student with a mentor who has experience in this field. Each student will begin this independent exploration during the summer before his senior year. When he returns in the fall, the senior will be charged with creating an artifact that captures what he has learned through his exploration. For example, a boy interested in film may produce a screenplay; a boy interested in poetry may choose to create an anthology of original works; a boy interested in engineering may produce a schematic design for a new bridge; or, a boy interested in music may build his own instrument or piece of music. Students, in short, will be challenged to dig deep into an area of emerging interest so that they can discover something more about it and themselves.

In The Element, Sir Kenneth Robinson argues that self-discovery and self-awareness forge a skill set of productivity and maneuverability that will enable young people to better navigate the turbulent waters of the rapidly changing world. The “element,” according to Robinson, is “the meeting point between natural aptitude and personal passion.” People who are in “their element” are “doing the thing they love, and in doing it they feel like their most authentic selves….Being there provides a sense of self-revelation, of defining who they really are and what they’re really meant to be doing with their lives.” The Trinity-Pawling learning environment will continue to search for those spaces where a boy can immerse himself into self-awareness and discovery. In a culture in which girls outnumber boys in colleges by almost a margin of 20%, this type of discovery and awareness could be a game-changer in the life of a young man. As I said, it is an exciting time to be an educator at Trinity-Pawling!

Posted by wtaylor on Monday May, 16, 2016 at 02:45PM

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A Commitment to Character

As we prepare young men for the world beyond Trinity-Pawling, we seek to convey this fundamental lesson: Character is the single most influential force to propel us forward - whether academically, physically, socially, or spiritually.

Trinity-Pawling has so much to offer!

Check out everything you can do and be in the pages on our site.  And if you'd like to contact us, we'd be happy to hear from you.  You can reach the admission office at 845-855-4825 or by email at

Not Just In the Classroom

What makes Trinity-Pawling unique? The Effort System is at the heart of everything we do.

The Pride

At Trinity-Pawling, every boy is a three-season athlete.  Whether he is learning the basics or has been excelling for years, he is part of the School's century-old athletic tradition.  T-P competes in the Founders' League, a highly competitive arena showcasing some of the nation's best prep school talent. T-P offers 13 interscholastic sports with 30 teams.

We're Seriously Creative

The Arts are an integral part of every Trinity-Pawling student's education. Whether they wish to develop existing talents or experiment with an entirely new form of expression, each student will have at least one year of music, theater, visual art or art history.


As a parent or guardian of a Trinity-Pawling student, you are a welcome member of the community. Your involvement through event attendance, participation in the Parents' Association, or simply staying connected is appreciated.

This could be you!

Over 100 years ago, Frederick Luther Gamage, Trinity-Pawling's Founding Headmaster, said, "Whether a boy succeeds or fails in the first instance at everything he tries is irrelevant.  The only boy who truly fails is the boy who fails to try."  Today, a century later, 315 boys live learn and grow together in an environment that fosters commitment, effort and character across the board.

Stay Connected!

Trinity-Pawling has a rich tradition of alumni connectivity. We want you to participate in the life and vitality of the School. Through this engagement, alumni will help Trinity-Pawling propel forward.

Stay Connected!

Trinity-Pawling has a rich tradition of alumni connectivity. We want you to participate in the life and vitality of the School. Through this engagement, alumni will help Trinity-Pawling propel forward.

As a convenience, Trinity-Pawling School links to Google Translation which provides an automated translation of our website. The tool is not perfect, and the context of the copy may not be precise when it is translated. As a result, sometimes the translation may lose some of its intended meaning. Therefore, Trinity-Pawling School cannot guarantee the accuracy of the converted text. Where there is any question, the English version is always the authoritative version of the website.

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