What my high school principal taught me about being young — and growing up

One day during my junior year of high school, my friends and I skipped lunch period to go to Wendy’s. Leaving school grounds without permission: a time-tested no-no. When we returned, our principal, Peter Anderson — who was patrolling the lunchtime courtyard sporting his two trademarks: a crew cut and a scowl — saw us trying to sneak through a side door. Once we realized that he had spotted us, a bunch of long-haired, hacky sack playing, Grateful Dead-obsessed 17-year-olds, we tried (without much tact) to backtrack on tip toes and go in the front entrance. Needless to say, we were caught, Wendy’s bags still in hand.

“Boys…” Mr. Anderson said, beckoning us over, in his deep, authoritative drawl. “That’s got to be the stupidest attempt to avoid me I’ve seen all year.”

We steeled ourselves for retribution, but instead, he took us into his office and made us a deal: we could serve the few days’ worth of the detention we so blatantly deserved, or we could…write him a song. We looked at each other, dumbfounded.

“Think about it,” he said. “See you Monday.”

Knowing my friends and I were musicians , Mr. Anderson figured some songwriting homework would be a more creative, lasting lesson than sitting in detention hall watching the clock tick by.

Monday morning, we came in, guitars in hand, and played him a song we had written over the weekend — a plea for mercy amidst the temptation of a Wendy’s frosty. It was, in my admittedly faulty memory, a song about an older person staring across the generational divide and remembering we were all young once. And dumb. And hungry. Or something like that. Mr. Anderson listened, stone faced, from behind his desk during the entire performance. Then as we finished, the outlines of a wry smile appeared near the corners of his mouth.

“Good song,” he said. “Don’t do it again. Get out of my office.”

Peter Anderson, who passed away this past summer at age 79, began his career in the Andover public school system, before becoming a principal in North Carolina and Illinois. In 2000, when my class began our freshman year of high school, he returned to the district where he got his start, this time as principal of Andover High. He joked that it was his freshman year, too.

The early word on Mr. Anderson was that he was a drill sergeant. He had a tough demeanor, demanded excellence and didn’t have a lot of room for nonsense. During a summer student leadership program before freshman year began, he gave the opening address and moodily asserted that he’d be deeply and personally disappointed if he didn’t return in three days to find that we had all become the future leaders, not just of our high school, but the next generation of America. I hadn’t spent a single official day in high school yet, and I was already petrified.

The out-of-town facilitator leading that summer workshop summed up how we all felt: “What’s up everyone? My name is Doug and I’m gonna be honest: your principal scares me. But in a really good way.”

I came to understand what he meant. Mr. Anderson set a high bar for his students. He expected us to work hard and challenge ourselves. If he felt you were taking the easy way out, he had no problem telling you. Loudly.

But he didn’t just make scary speeches and then lock himself in his office until graduation day, hoping we’d somehow figure it out. He made genuine, lasting connections. Some days, when I felt an undefined pang of teenage alienation, I would finish lunch in the cafeteria and go sit outside in the courtyard by myself (I know, so emo). Often, Mr. Anderson would walk outside and sit down next to me. On the surface, we had little in common (think Neil Young breaking bread with Robert Duvall’s Colonel Kilgore character in “Apocalypse Now”). But we forged a real relationship.

I learned about his son who was serving overseas, about his early years teaching and about the things he always said he valued: character over experience, humility over bluster, integrity above material success.

Recently, for reasons both generational (I now have two young boys) and chronological (I just turned 40), I find myself looking back at people who made a difference in my life. Some of them know their impact, but not all. Mr. Anderson retired years ago and moved out of state. Aside from a few brief encounters over the years, we mostly lost touch. But I’m not alone among my classmates in saying he was one of the most impactful people in my life, during the years when I most needed direction and an occasional kick in the pants.

The year after the Wendy’s incident, Mr. Anderson invited us — the same kids he could have thrown in detention without a second thought — to perform a song at our graduation ceremony at the Tsongas Arena in Lowell (cementing for eternity among our group that we have “played arenas”).

One of my favorite sayings is, “the true meaning of life is to plant trees under whose shade you do not expect to sit.” It reminds me of those who helped shape my life, especially those who are no longer here, and how those lessons learned will one day be part of what’s left for my own boys.

The quote is attributed to a man named Nelson Henderson, but when I think about it, more than two decades after the great Wendy’s caper, it’s still Mr. Anderson who comes to mind.