From New Jersey to California, and now online, musician still loves teaching after retirement.

Bill Dempsey has been a musician in one form or another since childhood. As a teacher, a performer and a history buff, he’s woven his skills and interests into almost every aspect of his life and still teaches today.

“Teachers never retire. When the COVID-19 pandemic hit I was contacted by a group of women in South Carolina who’d seen one of my videos and wanted me to teach them ukulele via Zoom. That was more than four years ago, and we’re still going strong. Also, I’ve worked as a professional musician since I was in junior high, and I still do a variety of gigs. Almost every teacher I’ve ever known has a side job, a second job—call it what you will.”

Dempsey’s teaching career began in New Jersey in 1973 where he grew up, and a dream of surfing led him to move to California in 1988.

“Since I was a kid, I’ve read surfing and car magazines. Everything in them was centered in Southern California, so one year I saved up my money, packed up my van and left in January in-between blizzards. When I came here, I knew no one, and the first year and a half I lived in a youth hostel in Huntington Beach. During that time, I found a teaching job at the Ocean Institute.”

That forced Dempsey to get creative by including music in his lessons. “I really loved teaching living history at the Ocean Institute, and to incorporate music, we sang traditional sea chanties. There was enough flexibility in the program to combine the two. And in the outdoor science program, we would get a few hundred kids to do sing-alongs on science subjects.”

What made you pursue a teaching career in music instead of history?

“I always wanted to be a musician. I love that you can get paid for teaching, playing music, and people applaud! What other kind of job can do that for you?”

Beyond applause, Dempsey found value in being part of a community. “I taught for more than 20 years in the Santa Ana Unified School District and being around like-minded people was important to me. In my experience most teachers like each other. I would go to the teachers' lounge at Monroe Elementary to eat my lunch and have my coffee break to get to know others. I taught there for 16 years. The teachers were supportive and positive.”

Dempsey found inspiration in helping students gain skills they could move through life with and knew that while at school, they were cared for. “Sometimes, coming to school is the only time that day students can get food and it chokes me up, thinking about it. Mostly I taught third grade through fifth grade students. I knew when these kids finished their education and wanted to pursue music, they had the basic foundations and knew how to read music.”

How did music become important to you?

In fourth grade Dempsey wanted to play the trumpet, but all the instruments were being used by other students, so he was given a trombone instead. This was challenging because his arms weren’t quite long enough to play the big instrument. “There are seven positions for the trombone, and I was a shorter kid so I could only reach four when I started. My parents were always supportive, and they got me private lessons in the eighth grade. Later, my mom told me they couldn't see me, but they noticed my slide wasn't in synch with the other trombone players.”

Did you have a favorite teacher? What did they teach?

“It’s hard to pick one, but the director of music in the town I grew up in was my favorite. He left me with a great love of John Philip Sousa and Henry Fillmore marches. Most of all he taught me pride. He said if I’m going to make a mistake, make it a good one, to play out and be proud.”

What’s one fun thing about you?

“I started playing music when I was nine years old, and I’ve never stopped. I started surfing when I was 14, and I’ve never stopped. I’m 73.”

What’s your best piece of advice for new teachers? 

“Always have a backup plan and never work a job just for money. If you’re in the arts, be prepared for a rough road and be flexible. I wanted to be a high school band director, and I hated it. I wound up teaching little kids how to play Twinkle Twinkle Little Star, and I loved it!  If you want to be a music teacher, get into a large school district because music is the first to get cut and you could move to different schools. Also, teaching is a team sport in my opinion. It’s the teachers, the administration and the parents that make it great.”

What are you enjoying most about retirement? 

“My wife Teri and I travel a lot. We’ve been to Hawaii more times than I can count—Jamaica, Puerto Rico, Caribbean cruises, and many places in the states, especially when visiting family. We’re currently planning a trip to Costa Rica early next year.”

Teacher Talk is a series of profiles on California teachers and other educators. To be considered for a future profile, email Communications@CalSTRS.com with Teacher Talk in the subject line.