With a Little Help: A Profile of Chuck Webster

By Lauren Hall 

“I was an inconsistent high school student to say the least.” It is surprising to hear such a mediocre self-assessment come from Chuck Webster, the head of University High School.  Webster oversees one of the best college preparatory schools in the nation, with a strong and commanding presence. But his firm commitment to and love for education was not always so definite. Not much in his life was. But with boosts from key mentors along the way, a winding road has led him to the collaborative and welcoming culture that he now proudly calls home.

Webster was born in Detroit and later moved to Birmingham, Michigan at the age of seven. Birmingham provided a comfortable suburban existence in which to grow up, but the culture was confusing to Webster. While wealthy and gorgeous, the town was filled with “country club wives who really weren’t on good terms with themselves.” The resulting mixed messages caused Webster to question the correct road to happiness. Money, in and of itself, certainly did not appear to lead to self-fulfillment.

“School didn’t like me, and I didn’t like it much either,” recalls Webster. As a result, Webster describes himself in high school as a “lost soul.” That all began to change when, in his words, “a teacher found me.” Phoebe Chow noticed the high school junior’s potential.   “She wouldn’t let me simply go through the motions and wouldn’t accept that I wasn’t smart,” Webster fondly remembers. With his teacher’s encouragement, he followed her to Oakland University, where he enrolled as an undergraduate.

While he had moved farther along in his journey, the road did not get any straighter. Webster would still not describe himself as “career oriented” and did not methodically pursue his degree. Instead, before completed his studies, he dropped out and began working many manual labor jobs, from coating metal with acid to undoing air hoses under moving trains. His work environment was in stark contrast to those in which he was raised and currently thrives. According to Webster, a fellow employee died in a workplace accident, and “three of the workers’ wives would have to come in to sign their husbands pay checks as they were illiterate.”

According to Webster, the Vietnam War distracted he and many others his age “from what we wanted to do in the future.” However, once again Webster benefitted from another mentor entering his life. After a six-year pause, he reenrolled at Oakland University and encountered Professor Jim Hart.   An otherwise routine film theory class that was led by the charismatic teacher became a turning point in Webster’s life. With Hart’s inspiration and guidance, Webster for the first time began to manage school, and as he describes “the rest of it just sort of fell into place.” Webster quickly finished his undergraduate degree, proceeded to earn a masters degree, and began the process of getting his doctorate degree.

Still unsure of his future, Webster hung around the university, finding kindred spirits with a shared love of literature. “Every Friday no matter what I had on my schedule, I was at a coffee shop discussing twenty books with my friends,” describes Webster. Now twenty-six years old, Webster still had not settled into a career path.

Unexpectedly, Webster and his future profession were united by a collision. In 1978, Webster’s car was damaged in an accident, and according to Webster, “you didn’t have to have auto insurance back then like you do now.” Faced with a $500 repair bill, he looked into a job opening at a school not far from where he grew up. The Roeper School needed an English teacher for a semester; Webster ended up staying for eight years.   His now ignited passion for education led him from that position to become the head of University High School.

At University, Webster has created an environment in which collaboration is highly valued. He operates with the motto “Take care of who you can take care of and people will take care of you.” That outlook carries forward to the students, who take a strong interest in each other’s success, and to the faculty, who are supportive of one another.   With great pride, Webster relayed a story of fellow teachers making a great effort to welcome and ease the transition of a new teacher.

Webster has used mentor/mentee relationships to strengthen University’s supportive culture. According to one of the students that he mentors, “he is increasingly invested in individual people.” The mentee further explained, “[Webster] is constantly telling us about our best attributes, so that we can improve and become the best versions of ourselves.”

Given the personal help Webster received along the way, it should be no surprise that University takes great pride in a supportive culture. Webster now finds himself in a collaborative educational environment that creates opportunities for students to receive the same benefits of personal mentorship that he once received. While the road has not been straight or always deliberate, a once lost soul has found his way home.