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Headmaster's Blog


Conscientious Discipline

My first paid job was that of a garbage collector one summer when I was nine years old. That summer, my father was on sabbatical on Iona, a small the island in Scotland. While my father and mother were enrolled in a program at the local abbey, my six year old brother and I were left to entertain ourselves while safely trapped on the island.

To facilitate our entertainment and to promote goodwill with the locals, my father created a work-study program for my brother and me. For each piece of garbage we collected on the island, he would reward us with one half of one pence. While not fully aware of the relative value of the British currency as it related to the price of a candy bar or ice cream, I did grasp that an island beautification campaign could be a windfall. Each day, then, we hunted for garbage and each afternoon we counted our trove that was measured toward our weekly payout.

By collecting garbage, I was rewarded with candy, ice cream, and memorable days spent exploring the island. This job, though, also reaped other benefits that became apparent years later. First, I still collect garbage. I am always picking up pieces of litter around campus and even away from school. Secondly, and more importantly, the garbage collecting job provided me with an opportunity to exercise conscientious discipline on a daily basis. This practice led to other paid work experiences in middle and upper school such as delivering newspapers, cutting lawns, shoveling snow, and working in a supermarket. Before the age of 18, I had many experiences that demonstrated to me the rewards and value associated with conscientious discipline. Importantly, the practice of conscientious discipline also carried over to my academic responsibilities on a daily basis.

Trinity-Pawling School compels me as an educator because of the emphasis of conscientious discipline that pervades its learning culture. Aristotle wrote, “We are what we repeatedly do. Excellence, then, is not an act, it is a habit.” At Trinity-Pawling, boys learn that details are a critical component of excellence and finding success. They learn that the value of an education is not measured solely by what can be known, but what problems can be solved. They learn that asking the right question is just as important as knowing the correct answer. They learn that effort reflects character and that their character is something built and strengthened over a lifetime. They learn that a community must enriched through acts of kindness, charity, and forgiveness. At Trinity-Pawling, boys learn that the camaraderie of brotherhood creates bonds of friendships they will share for a lifetime. They learn that a school can be like a family and the mutuality that exists with their teachers is a powerful dynamic that distinguishes their learning and their growth as young men. They learn that honor is something to be respected and protected. Boys learn by doing at Trinity-Pawling and this can be joyful. In this process, they discover that conscientiousness builds confidence and is the key toward unlocking the potential for greatness that each of them possess.

In his book, How Children Succeed, Paul Tough touts the importance of conscientious discipline and its importance in helping young people learn the measures of success. Tough’s book is an insightful analysis of how certain character traits are predictors of various forms of success in adulthood. Individuals with high qualities of conscientiousness, writes Tough, achieve at higher levels in high school and college, are physically healthier, and are high achievers in the workplace. While it may be customary to associate success with conscientiousness, the research demonstrates that conscientiousness is a trait that can be nurtured and grown. For Trinity-Pawling School, this research is validation of a learning environment that has been helping boys find their greatness as young men and leaders since 1907.

Posted by wtaylor on Thursday September, 3, 2015 at 03:11PM

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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.


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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.

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