Tom Woodward’s Unusual Journey to MA

February 7, 2017

It is eight a.m. on a Friday morning and Tom Woodward is ready to start his A Block Constitutional Law class. His 18 students are sitting at chairs with desks attached arranged in a semicircle around the outside of the classroom, with Woodard sitting at the front of the class at one of those same desks. He leans back in his chair to stretch, looking completely in his element as he instructs the class to take out the US Supreme Court cases they had read for homework. A twenty-minute discussion ensues in which the class reviews the homework before breaking away to work on a project.

Woodward conducts the class with a unique combination of relatability, humor, passion, and ease. He almost looks like a student sitting at his desk with his heavily annotated copy of the cases, yet he commands complete attention of the room. He allows the class to get sidetracked, joining in fully on conversations about anything from ADHD to the inauguration. He then somehow connects the completely unrelated topic back to the Supreme Court so subtly it’s hard to realize it’s happened until the class is speaking once again about Loving v. Virginia. His signature dry, borderline inappropriate, humor also makes a clear appearance in his class. He makes the class laugh nine times in 20 minutes, something very impressive considering it is so early in the morning.

After 28 years at MA, Woodward has become a pillar of the community. Not only do students love his personality, I actually interviewed him because so many people asked me to bring back the short video segments Talks with Tom in which Woodward would answer many random questions quickly, but they also love his classes. Given all this, it may seem obvious that Woodward would end up teaching history in Marin. But he was never so sure he even wanted to be a teacher.

“Right after college, I worked for a lawyer as kind of an assistant. Oh, it was miserable. I was trying to decide if I wanted to be a lawyer,” Woodward says.

Growing up in suburban Philadelphia in a family full of teachers, Woodward attempted to “delay the inevitable” of a career in education from a young age. As a kid, he wanted to be a professional athlete, first as a relief pitcher for the Red Sox, “talk about great hours, holy cow,” and then as a professional golfer. Right after college, however, this desire to experience something new came in the form of law.

“I couldn’t decide if I wanted to go into teaching because it was kind of the family business,” Woodward explains. “I was trying to decide, ‘Am I doing this because it is a family thing or do I actually want to do it?’ So, I thought about maybe doing the law thing.”

The long hours quickly killed Woodward’s idea of being a lawyer. In retelling the story, Woodward describes his decision to leave law with a simple “eh, I [didn’t] want to do that.” This sense of nonchalance is the centerpiece of the way Woodward speaks throughout the interview, especially as he describes what he did next.

“I went to acting school in New York for a year,” Woodward says.

Although Woodward is known to be a Netflix connoisseur and often seems to be an amateur stand-up comedian, I would have never thought Woodward would have actually pursued acting. In fact, in retelling this to other members of the community one person choked on the water they were drinking, another burst out laughing, and yet another simply stared at me. But even as I express clear shock in hearing this to Woodward himself, he does not even flinch, nor does he make eye contact with me. He simply continues to tell the story.

Photo Courtesy of Tom Woodward
When I asked for images of Woodward from his past for this article, this is the first thing he sent me.

“I thought it would be fun,” Woodward says with a shrug. “You could meet girls, you know. I did a lot of acting in high school and college and I really liked it so I thought, ‘eh let’s see what the New York thing looks like.’ But it was, talk about competitive, oh my God, it was pretty bad.”

Despite its competitive nature, Woodward actually really enjoyed acting. He only gave up acting, and finally went into teaching, out of necessity, “I got married and my wife got pregnant,” Woodward says. “We needed an income, so that’s why I broke away from that. That’s why I became a teacher. I needed money.”

Photo Courtesy of Tom Woodward
Woodward and his son are still close; here they are golfing together in Southern California.

The cadence of his voice changes for the first time in the interview as he speaks about his first teaching job, something he truly hated.

“I was teaching compulsory drama to middle schoolers. Oh God, that was dreadful. I wanted to be a history teacher but I couldn’t find anything. Trying to teach compulsory drama to eighth grade, particularly eighth-grade boys, who don’t want to do it,” Woodward says as he sighs, shaking his head.

The monotone returns as Woodward describes how he left that job quickly in order to move to Los Angeles. He and his wife moved to take care of his mother-in-law following the death of his stepfather-in-law. Although he stayed in LA for two to three years and got his first job as a history teacher, Woodward stresses two things he is known to hate, overcrowding and bad weather.

“LA was way too crowded. Oh my God, it was so crowded,” Woodward says as he shakes his head, putting his head in his hands. “There are 10 million people in the LA basin a full third of the California population. It is just insane. There’s just nothing I liked about it, at all. [Even the weather] was too smoggy.”

Their experiences in LA led Woodward and his wife back to the East Coast, this time to rural Vermont. However, the harsh winters quickly became too severe for them and they returned to Southern California once again, this time to Ojai to teach at the Thacher School.

After three years at Thacher, he got divorced and followed his son to Marin, “My ex-wife had friends here, so she wanted to come up here. I wanted to stay near where my son would be, so I thought, ‘oh ok.’ Also, my friend from college, his wife was the college counselor [at MA]. So she said, well I’ll see if I can get you an interview or something,’” Woodward says.

Even after the interview, it was a fluke he got the job as a history teacher at MA.

“It turns out they hired somebody else. So I thought, ‘oh ok well that’s how it goes.’ Then in June, they called me and said that that person had backed out of their contract. They signed a contract, then decided they didn’t want to teach in a private school. They asked me if I was still available,” Woodward says with a laugh. “I said, ‘I don’t know I’ll have to check.’ I checked really fast and said yes.”

Before this point, Woodward has told the stories of finding his career, the birth of his son, and his divorce with the monotonousness of a story he’s had to tell a thousand times. But he seems surprised, still, that someone had backed out of their contract leaving him with the job of history teacher at MA.

Twenty-eight years later, Woodward still seems surprised he ended up at MA. While Woodward didn’t plan to teach at MA for so long, he definitely does not regret it.

“I had no idea [I’d be here for so long], no idea,” Woodward says with a slight smile. “I never thought it’d be thirty years. I just woke up one day and was like, ‘woah, 25 years.’ ”

Woodward and I then switch to a conversation about movies, TV, and social media. After a 55 minute interview during the last block of the school day, and basically mid-sentence, Woodward starts to get up and walk out of the room.

“Can I go home and take a nap now?” Woodward says with a laugh.


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