William W. Taylor, Trinity-Pawling School

Local heads of school in Westchester, Fairfield and Dutchess counties talk about lessons learned from the pandemic, inspiration, superpowers, what makes them smile and – in one case – the benefits of dogs on campus.

Founded in 1907, Trinity-Pawling School is a college preparatory boarding and day school located on a 230-acre campus in Pawling, where the school serves boys in grades seven through 12 and offers a postgraduate program as well. 

Taylor earned a bachelor’s degree at Kenyon College in 1985, and while subsequently working in advertising, he had an epiphany that he wanted to pursue a career that emanated from a commitment to service — which led him to earn a master’s degree in religion at Yale University. Taylor later served as president of St. George’s Independent School for 14 years. In 2015, he accepted the position of headmaster at Trinity Pawling School, where he had served as associate headmaster in the 1990s. He and his wife, Jennifer Luce Taylor, are parents to two adult children.

Tell us something surprising about your school. 

“Among the many successful alumni of the school is Frank Morgan, who played Oz in ‘The Wizard of Oz’. His legacy is a reminder to have a bold vision but to not let such boldness obscure the fundamental value of humility.”

How did your school cope during the pandemic? 

“We placed a significant amount of focus on emphasizing our collective responsibilities to serve and protect the health of the common good of the community. It was a very successful navigational objective and we made it through the year with minimal exposure to Covid. 

“Like most boarding schools, we did not bring students back to campus for the short period of time in between Thanksgiving and Christmas vacations. Instead, we focused on project-based learning while being remote. This was highly successful. When we return to school (this fall), we will be on campus for this period between the two vacations, but we will use this time for experiential, project-oriented teaching and learning rather than traditional classes.” 

Which aspects of running a school are most appealing to you? 

“I enjoy being a part of the transformational process of growth in the lives of young people by providing foundations of timeless values that are bolstered by the introduction of skills and learning motifs that will be expected of them in an ever-changing world.”  

What superpower do you bring to the school? 

“Vision. Prior to beginning my tenure as headmaster at Trinity-Pawling, I led the venture of creating and leading an independent day school. It was in this process that I discovered that I had strengths that combined having a vision of what did not yet exist with an ability to build the foundation and supporting structures to support this vision so that it reaches fruition. I have used these skills toward creating an innovative curriculum for Trinity-Pawling, as well as other forward-thinking initiatives at the school.”

What led you to choose education as a career? 

“I wanted to have a career where I could help young people discover the joys of learning and help them reach toward their potential as human beings.” 

What reaffirms your career choice?

“I am reaffirmed whenever a young person begins to realize that they possess distinctive gifts and talents — and that these gifts and talents are qualities about themselves that they can begin to access, through the assistance of talented teachers, to find the joys of learning and the passions of life.”

Did you have a favorite teacher who affected your life? 

“I credit Mr. Sam Hougas of Darien High School, who had the most profound impact on my career choice. Not only did he help introduce me to the joys of studying history, but he also challenged me to become a more complete and thorough student. He was a mentor who saw strengths in me that I could not see at that age.”

How do you recharge in your free time? 

“I like to recharge by finding time to reflect on walks, playing golf, riding my bike or listening to music. I also enjoy reading as a means to introduce new insights and revelations.” 

Trinity-Pawling School at a glance

  • Head of school: William W. Taylor
  • Number of faculty and staff: 60
  • Student enrollment: 200
  • Annual tuition: $47,000 to $66,000 

For more, visit trinitypawling.org.

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