A Teacher at Heart

“He said, ‘Billy Peebles…is that what you go by?’” Collegiate’s Interim Head of School recalled one recent morning as his two-year stint on North Mooreland Road as well as his distinguished career in education spanning four decades was coming to a close. “I said, ‘Yes, sir.’ He said, ‘That doesn’t sound like a headmaster’s name to me.’  I said, ‘Well, that’s my name.’”

 

As he relayed the story, Peebles smiled, which he does quite often, then added, “I quickly figured out that that wasn’t a place I wanted to be anyway.”

 

William S. Peebles IV is his given name. His great grandfather, who founded the Peebles Department Store chain in 1891, was Will. His grandfather was William. His dad was Bill.

 

He’s been Billy all his life, even when he ventured at 14 years old from his home in Brunswick County, near Lawrenceville, to Episcopal High School and later Princeton University, when he taught, coached, and undertook various administrative roles when he was just slightly older than his students, and later when he served as head of three schools and fulfilled three interim assignments.

 

At every stop, his colleagues, regardless of job designation, have called him Billy, which speaks loudly and clearly to his humility, lack of pretense, authenticity, Solomonic wisdom, soft-spoken manner, and innate understanding that to command respect, one must show respect.

 

His name, you see, is his identity.

 

“It’s who I am,’’ he said.

 

His position notwithstanding, Billy Peebles is a teacher in the noblest sense, and, true to his nature, he’s quick to credit those who inspired him throughout his journey, which includes 36 years as a school head.

 

“Growing up, I picked up early on, as did my three siblings, how important my parents felt education was,” he said. “They always said, ‘It’s the one thing we can give you that nobody can take away.’”

 

In the fall of 1969, Billy headed off to EHS, where he thrived.

 

“When I left Episcopal,” he said, “I wrote my headmaster, Mr. [Flick] Hoxton, my assistant head Mr. (Sandy) Ainslie, and some other faculty who had meant so much to me to thank them and tell them that because of my experience, I thought I wanted to teach. Except for college and graduate school and a year in the business world, that’s what I’ve done for 41 years.”

 

With three semesters remaining at Princeton, Peebles took a year off and served an internship at Virginia Episcopal School in Lynchburg. A teacher there became ill, and Peebles assumed his teaching (history), coaching (JV football and lacrosse), and advising duties.

 

“That gave me additional impetus to want to teach,” he said. “Of course, we violated every accreditation standard imaginable because here I am teaching these classes without a college degree.”

 

After he returned to Princeton and completed his A.B. in politics, Ainslie, now the VES headmaster, hired him at age 23 to teach American history and serve as director of admission and financial aid.

 

“It was a fabulous learning opportunity,” he said. “It was demanding. I loved every minute.”

 

He remained for four years, then worked a year as assistant manager of the Peebles Department Store in Woodbridge, Virginia.

 

“It was a great experience,” he said, “but I quickly figured out that I wanted to get back into teaching.”

 

His course charted, Peebles enrolled in the University of Virginia’s Darden School of Business and earned his MBA, which, he felt, would help him in his future endeavors because he now aspired to be a school head.

 

During his second year in Charlottesville, that call came from Powhatan School, a K-8 institution with 140 students located in Boyce, Virginia. After seven meaningful and fulfilling years there, he, his wife Penny, and their young daughter Sara moved to the Asheville School in western North Carolina.

 

“I’d spent those years at VES, and I yearned to get back into the boarding school business,” Peebles said. “I missed the sense of community where you’re living literally with your colleagues and with the kids.”

 

A decade later, he stepped away once again, this time to devote a year to study and reflection at the Virginia Theological Seminary in Alexandria.

 

“There was clearly a spiritual dimension, but in many ways, it was as academic as it was spiritual,” he said. “I’d gotten very interested over time in theology, especially the role of religion in American history.”

 

One of his projects culminated with a paper about Abraham Lincoln’s religious journey, which Peebles described as “a very interesting, unorthodox, far-from-linear process because he actually started out in many ways as a non-believer and over time acquired a real commitment to faith.”

 

His scholarly research into Lincoln’s odyssey was hardly a passing fancy, for he had long before developed a profound respect for the 16th president.

 

“I revere Lincoln for many reasons,” he said. “His reverence for words. He had the equivalent of one year of formal education. Most historians consider him as our best writer as a president, rivaled only by [Thomas] Jefferson, who had the best education money could buy.

        

“His lack of ego. The Team of Rivals story where he brought in [William H.] Steward, [Salmon P.] Chase, and [Edward] Bates [to his Cabinet]. All three were candidates for the Republican nomination. All three had a low opinion of him. All three thought they were better qualified to be president. He ultimately won them over.”

 

He referenced, also, Lincoln’s ability to remove himself, albeit briefly, from the cacophony of daily life.

 

“I worry today about our kids not having enough solitude, about not knowing how to do nothing,” he said. “That’s when we get our most creative inspiration. During the four years of Lincoln’s presidency, he went to the theater more than 100 times. He knew he’d be criticized for that, and he was. People thought it was frivolous. Where is he? We need him to have a hand on the throttle. Run the ship of state. Right?

 

“He said he needed to be in a different place. It was a different setting than making policy about war and government appointments and managing egos. It required enormous discipline to pull away, particularly when you think about the challenges of his time. Pretty amazing.”

 

As was Lincoln’s example of great leadership, which Peebles has modeled throughout his own personal and professional journey.

 

“A huge responsibility of leaders,” he said, “is to discover the talents in the folks around you, help them become their best selves, and, from Lincoln’s first inaugural address, appeal ‘to the better angels of our nature.’”

 

In 2003, Peebles answered the call to head Lovett School in Atlanta, where he remained for 15 years.

 

“I knew it was time,” he said of his departure. “I’ve always said to my board chairs and trustees that I need to figure out a year before they do that it’s time for a new voice. You really have to want to be a school head. You can’t be intimidated by the challenge or ambiguity of it. Schooling can sometimes get messy. I’ve always enjoyed figuring that out. There’s always plenty to figure out in this business.”

 

In 2018, he and Penny settled in Richmond to be close to family and friends. He hardly stayed put, however. He’s served on several boards as well as one-year stints as interim head at Palm Beach Day Academy and Powhatan School before joining the Collegiate team in July 2022.

 

“I’ve been asked what distinguishes Collegiate,” he said. “It’s the fundamental kindness of the kids and the respect they have for their faculty. The kids have been so good and kind to me as the interim. I think that’s genuine. I don’t think they’re doing that because I just happen to be in this office. I think that’s the way they’re wired. I feel so fortunate to wrap up the 41 years in teaching here.”

 

“Forty-one years in teaching” isn’t a slip of the tongue. Peebles, you see, has always considered himself a teacher at heart. In fact, wherever he’s been, teaching at least one class each semester has been part of his regimen.

 

“Teaching reminds me why I entered the profession to begin with,” he said. “That’s what I’ll miss the most. It’s an uplifting experience that arms me with the energy to do the other things I need to do.

 

“Not every day in the classroom is a picnic. Some days, you’re on. Some days, not so much, but when you have those days when you feel the energy and the lights go on with the students, it’s magical. We’ve all had them. It’s hard to describe, but you know it when you see it and feel it. Hopefully, I’ll have the opportunity to continue teaching somewhere down the road. I’ve always taught, and I’ve been grateful for that privilege.”

~Weldon Bradshaw