Derek Kirk ’01, Third Career Teacher

Teaching is the third career path for Derek Kirk, and the third time’s the charm. For him, what greater purpose in life is there than to do very meaningful work in changing young people’s lives? When he saw the opening for an assistant teacher position at Windward during the summer of 2020, he felt that “it was an amazing opportunity to return to a school that was so impactful with me academically to now guide me as an instructor. I knew that Windward would be the perfect place to hone my craft as a teacher.” 

“It was an amazing opportunity to return to a school that was so impactful with me academically to now guide me as an instructor. I knew that Windward would be the perfect place to hone my craft as a teacher.” 

Derek attended Windward as a student for two years. He spoke fondly of two of his former teachers, Sheila Okin and Adele Barracca, for teaching him multiple organizational strategies to improve his writing composition, including planning, notetaking, and quick outlines.  

“When I learned about how to outline a paper, that was a gamechanger for me as a student,” said Derek. “There are still sentence starter charts on the walls in Windward classrooms, so it’s nice to see certain things haven’t changed. I continued to organize my work in the same way when I was in graduate school and drafting research papers and theses.” 

After Windward, Derek attended Horace Greeley High School in Chappaqua, and he excelled academically by retaining the writing skills he learned. Plus, he advocated for himself,  he used the accommodations he was entitled to, and he had extra support from his high school resource room. Derek moved on to receive his bachelor’s degree in communications from Quinnipiac University. He grew increasingly confident in his academic ability, so Derek was proud to have completed his second higher ed degree, a master’s in public administration with a focus on healthcare, from Pace University without using any accommodations. 

Derek then began his career in the healthcare and finance arenas as a financial analyst at White Plains Hospital. He continued to work in small medical practices as an accountant, medical billing operator, and payroll coordinator. A decade passed before Derek had a lightbulb moment. A close friend of his that he met at Windward was describing their experience as a teacher, and he realized that he wanted to leave behind healthcare and finance and explore a new career possibility of teaching. 

Derek completed Pace University’s master’s program in childhood education in 2019. As part of his coursework, Derek acted as a student teacher in Chinatown and observed public schools in the Upper East Side. “Once I was in front of the classroom, I truly felt that this was the perfect move for me. I love working with students and giving them the tools that I learned over the years.” 

The following year, Derek returned to Windward as an assistant teacher at the Manhattan Middle School. In his first year, he had a fantastic time working with Olivia Gennusa as his mentor teacher in language arts classes. This year, he is working with Shirley Hwang, Ruby Silverstein, and Ellen Colton across all academic disciplines. Additionally, Derek is leading a pilot program of new computer classes three times a week.  

Although the Manhattan campus did not exist yet when he was a Windward student, the program and overall student experience still ring true for Derek. “When the students were doing writing samples at the beginning of the year, I could sense their frustration about the painstaking amount of time it took them to brainstorm ideas and put them into an outline,” said Derek. “I totally remember what that was like. Until I came to Windward, I didn’t have any idea how to begin and come up with a plan to write. Seeing the progress of the students and watching them gradually build their toolkit from the fall to the summer really spoke to me, because I noticed much of that change in myself as a Windward student.” 

Derek has been impressed with the growth of Windward, expanding from one building in Westchester to three campuses and four divisions. “It’s fantastic the School has thrived in the years since I have been a student. It’s an important school and helps so many people. It is so important that a school like Windward exists.”