From First-Generation Student to Mentor: Meet Tim Cushing

Director of Communications Marybeth Bentwood recently sat down with our incoming Director of College Counseling, Tim Cushing, to discuss the journey that shaped him—and the students he hopes to serve.

Tim joins Holderness this summer after nearly a decade at Brewster Academy, bringing admissions experience and a deeply personal commitment to his work. As a first-generation college graduate, Tim knows firsthand how transformative the college process can be—not simply as a pathway to acceptance letters, but as a time of growth, self-discovery, and confidence.

Tim is originally from the greater Plymouth area, having graduated from Plymouth Regional High School in 2006. He then attended Stonehill College and graduated in 2010 with B.A. degrees in Psychology and Visual and Performing Arts, with concentrations in Music and Theatre.

Tim began his career in college admissions, spending seven years working at Stonehill College, Babson College, and Wheaton College. His work in admission gave him a comprehensive understanding of the application review process, institutional priorities, and how students can most effectively present themselves.

In 2017, Tim switched sides of the desk and began working in college counseling at Brewster Academy. In 2022, he was named Dean of College Counseling. In that role, he was responsible for counseling students through every stage of the college and financial aid process while supervising a team of counselors. Tim prides himself on being fully committed to student-centered decision-making, building long-lasting relationships with students and families, and focusing on authentic fit in the college process. He believes the college search is not simply about admission results, but about helping students grow in confidence, clarity, and self-understanding.

A Leader in the Profession

Throughout his career, Tim has been deeply involved in national and regional professional organizations. He currently serves as the President of the Lakes Region Independent School College Counseling Association (LRISCCA) and previously held numerous leadership roles within the New England and National Association for College Admission Counseling (NEACAC and NACAC), including Chair of the Summer Institute, Governing Board Member, Assembly Delegate, and member of the Professional Development and Finance Committees. He presents regularly at regional and national conferences. Tim remains committed to professional development and maintaining strong relationships with colleges and universities.

In addition to his work in counseling and admission, Tim has a passion for coaching. He served as an Assistant Coach for the Men’s and Women’s Tennis programs at Wheaton College while working in admission. At Brewster Academy, he was the Head Coach of the Boys’ Varsity Tennis team until 2023, leading the program to its first-ever Lakes Region Championship. He also serves as an Assistant Coach for Brewster’s Boys’ National and EYBL basketball program, helping the team capture a Prep National Championship in 2020 and reach the Final Four at Chipotle Nationals in 2025.

Helping Students Thrive

He believes college counseling is about far more than “getting in.” It’s about mentorship: helping students understand who they are, what matters to them, and where they will thrive. Having worked in college admissions, Tim offers an insider’s perspective — insight that helps demystify a landscape that has grown increasingly complex.

At the heart of his philosophy is a simple but powerful idea: bring humanity back to the process. Behind every application is a young person becoming more fully themselves. Tim sees his role as guiding that growth with clarity, honesty, and belief.

He is energized by Holderness's leadership and mission, inspired by the care students show for one another and their community, and deeply grateful for the opportunity to return to his hometown. Outside of work, Tim enjoys being on the lake, boating, playing and listening to music, watching and playing sports, working out, and spending time with his family and friends.

This summer, we are proud to welcome a counselor who understands that the college journey—at its best—is about becoming.