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From classroom to Zoom

‘The sky’s the limit if you want to embrace technology,’ says Bill Holiday, whose anything-but-textbook journey will end after nearly 50 years in education

BRATTLEBORO—Ask which Vermont teacher was most plugged into technology before the COVID-19 pandemic, and colleagues point to Bill Holiday, one of the seemingly few adults who can singlehandedly juggle Google Classroom, Skype, Facebook, and Twitter without help from a student.

“I’ve been paperless for more than a decade,” the Brattleboro Union High School educator says. “I deliver resources now the same way I have for many, many years.”

But Holiday, 70, isn’t some upstart showoff. Instead, he is believed to be the longest serving teacher working in Vermont today — a fact the state Agency of Education can’t confirm, only because his 1972 introductory forms were filed well before the start of its digital database.

A member of Brattleboro’s class of 1968 when the interstate was under construction and the term “information superhighway” had yet to be coined, Holiday recalls the day he stopped paying attention to his history instructor to ponder his summer job on a paving crew.

“I remember saying to myself, ‘You can tar roads for the rest of your life — no disrespect — or you can use your brain to do something like this,’” he says.

Holiday went on to study at the since-closed Windham College in nearby Putney and student-teach in the Windham Southeast School District, where he has worked for nearly a half century.

“My first day, the principal took me aside and said, ‘Here are the textbooks.’ I opened up the first chapter, and the first sentence was, ‘To know London is to know England.’”

Holiday winces now the way he did then.

“And so, to know New York City is to know America?” he thought. “That’s the last textbook I ever used.”

Hours of graduate school at night, on weekends, and during the summer honed this thoughts about teaching.

“As I sat there absolutely bored to death, I asked myself, ‘Are you doing this to kids?’”

Holiday teaches history by tapping primary sources and personal travel, having visited tourist-friendly North America and Europe as well as such world trouble spots as Cuba, Northern Ireland, and Vietnam.

But don’t look for him to share observations on a chalkboard or mimeographed handout.

“I constantly lamented being in that infernal copy room churning out reams of paper that would land on the classroom floor,” he says.

And so, Holiday moved to overhead and computer projectors.

Take the time the teacher logged onto his laptop to connect via Skype with the grown son of the late Soviet Prime Minister Nikita Khrushchev, who was 8 hours ahead and 4,500 miles away in Moscow.

“He was a 27-year-old advisor to his father during the Cuban missile crisis,” Holiday told his class. “I was your age when that happened.”

Holiday, fascinated by issues of war and peace, also has video-chatted with speakers from Vietnam (who stayed up until midnight to accommodate a 12-hour time difference) and hosted an in-person appearance by Daniel Ellsberg, the U.S. military analyst who leaked portions of the top-secret Pentagon Papers revealing the government’s history of intervention in Indochina.

“I talk with eyewitnesses to historical events in this country and around the world,” the teacher says. “The sky’s the limit if you want to embrace technology.”

Unlike most colleagues, Holiday was well-positioned to continue his lessons when the threat of COVID-19 forced schools to move online this year.

Even so, he has faced obstacles.

“There’s very little human contact,” he says. “There’s nothing like an exchange person-to-person.”

The teacher also has found opportunities.

“For better or for worse, the general nature of public education is to provide all the structure to the point of micromanagement,” he says. “One of the worst questions I get asked is, ‘Just tell me what I need to do to pass.’”

“The answer isn’t that simple,” he says. “I tell students, ‘I don’t know what you can do, but what’s more tragic, you don’t know what you can do.’”

“With students at home now, they have to budget and balance their own schedules,” Holiday observes. “In the final analysis, we all may be better for it.”

Looking ahead by looking back

Holiday knows today’s headlines seem unprecedented, but he can point to the past influenza pandemic of 1918, centuries of racial strife, and the financial panics of 1837, 1873, 1893, and the 1930s.

“We don’t use the word ‘depression’ anymore, but we’re in one right now,” he says. “Almost nothing is new. Virtually everything that happens I can put into the context of history.”

Now, so can his students. Many have participated in peaceful demonstrations on issues ranging from civil rights to President Donald Trump’s Cabinet picks.

“The lessons aren’t lost on students,” Holiday told the press in 2017 when students held signs with such slogans as “Fight for Your Future” to protest the appointment of U.S. Education Secretary Betsy DeVos. “They’ve decided to be a part of history rather than just read about it.”

Holiday has lived that philosophy since his first day on the job.

“I remember saying to myself, ‘If I ever wake up some morning and sigh, ‘I’ve got to go to work,’ I’m getting out. This is not a job that anybody should do unless they’re 100 percent committed.”

That said, the teacher is set to retire this month — but only because his wife is, too. (As outgoing superintendent of the Windham Southeast School District, Lyle Holiday is his boss.)

“When I started, there was no Gulf War, no Operation Iraqi Freedom, no Afghanistan,” he says. “I’m now teaching 50 years more history. But this job has been a labor of love.”

Holiday says the same about his past stints coaching football and boys and girls basketball, as well as his present side gig as a play-by-play announcer for Colonels sports on WTSA radio.

Named “most versatile” in his 1968 yearbook, he notes the evolution of records, cassette tapes, and CDs.

“They’re all gone — everything’s now in the cloud,” Holiday says. “Is it better than it was? It’s different. You move on, you adjust.”

“My job isn’t necessarily to teach everybody everything,” he says. “My job is to put people in a position where they can learn, and sometimes that means getting out of the way.”

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Originally published in The Commons issue #566 (Wednesday, June 17, 2020). This story appeared on page A1.

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