Barrington's Teacher of the Year: Connie Oswald

Middle school math teacher focuses on connecting with students

By Josh Bickford
Posted 9/20/23

Connie Oswald was humbled to learn that she was Barrington’s Teacher of the Year. The Barrington Middle School math teacher said she loves working with students and feels rewarded each …

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Barrington's Teacher of the Year: Connie Oswald

Middle school math teacher focuses on connecting with students


Connie Oswald was humbled to learn that she was Barrington’s Teacher of the Year.

The Barrington Middle School math teacher said she loves working with students and feels rewarded each day. Oswald said she was flattered to be nominated and selected for the distinction — she feels fortunate to work in a district with so many dedicated educators and draws her passion for teaching from the students she leads and all those she has taught in the past. 

“I know, if I think of myself and I think of the time I’ve been in Barrington, and even when I was out on the Indian reservation or when I was up in New Hampshire, wherever I was teaching, the kids were the most important thing in the world to me,” Oswald said. “And making sure they learned and making sure they felt so happy to be in my room. I don’t know, that’s all I’ve done for all these years. I’ve never been a person that needed big accolades. I never needed to be the head of this department or the head of that department. I’m not that kind of a person.”

Barrington Middle School Principal Andy Anderson said that while Oswald may not aim for the accolades she is definitely deserving. 

“When the opportunity came up for the middle school to nominate a teacher, it was really a no-brainer for me to have Mrs. Oswald representing the middle school,” Anderson said. “When you think about Mrs. Oswald you think about the impact she has on her kids. It’s not just the cluster kids in front of her. It’s the thousands of kids who came before the current cluster that she’s made an impact on. It’s everything that we’ve been acknowledging. It’s taking the time to get to know the individual kids as individuals, getting to know what their interests are. Just be able to really connect with them.”

Oswald prides herself in that connection. The longtime educator said building relationships with students and their families is paramount. The key to those relationships, she said, is made through conversation. 

“Every day we talk,” she said. “I probably talk to every single kid in my class every single day. Lots of kids. I always offer to stay after school or come in early. Tons of kids do that.”

That effort yields connections that last long after students move out of the middle school, even after they graduate from Barrington High School. Oswald said that after she was named Teacher of the Year she received congratulatory texts from some former students who are now in college. 

She recalled one text that stated: “It’s about time. You’re the one who does it right.”

“That means the world to me,” Oswald said. “And I think it’s because I make everybody feel good about learning. I have a quote in my room that my kids all put into their interactive notebook for math… ‘We all come in at a different place. We all learn at a different pace. And we all celebrate our learning, and we’re not in a competition.’ I’ve stressed that every day. I think the kids feel they know they can trust me, they know they can rely on me to help them whenever they’re struggling.

“That, to me, is my achievement.”

Oswald said her position offers plenty of challenges — the toughest is helping those students who are just not comprehending the material. 

“There’s going to be times when I give a test and somebody really, really doesn’t feel like they were properly prepared. I’m hard on myself then,” Oswald said. “What did I not do? I can’t just say that I taught so you’re supposed to know, because we all learn at different paces. We all learn in a different way.”

Anderson said teaching middle school math can be particularly challenging, but Oswald does a great job navigating the obstacles. 

“Middle school math is tough,” Anderson said. “You’re leaving the concrete to go to the abstract, and sometimes kids who don’t identify as being good at math they kind of feel that ‘I’m never going to be good at math.’ But Mrs. Oswald is able to breathe confidence in them for them to see themselves as mathematicians and math students. And she has, with thousands of students…”

How it started

Oswald was still a student when she realized how important teachers are. 

She was in high school when she came to know and appreciate her chemistry teacher, Sally Candon. 

“I grew up in West Chester County in New York, and I went to a private high school, but my family was going through a bad time and I did not always want to go home,” Oswald said. “And Sally lived a block from my grandmother in the Bronx. And I loved my grandmother. She was the most important person in the world to me. Sally would drive me down, drop me off at my grandmother’s. She’d pick me up the next day.

“I was at school a lot. It made such a difference to me. Everything. My academics did so much better because I felt like somebody cared,” she said.

Oswald went to college in Massachusetts and studied to be a doctor. She wanted to help people, she said. But in her sophomore year, she faced a tough situation when her father became sick. 

“I knew that I was the oldest in my family — how was I going to pay for med school? It just didn’t all fit together that it was going to happen,” she said. 

Oswald started thinking about different career options and decided to try education.

“I tried it out and my professors were like, ‘You’re the most natural teacher we’ve ever seen,’” she said. “I was graded on four qualities that would show to them that I was a good teacher: Courage, flexibility, a sense of humor, and understand kids. 

“If you were going to make it as a successful teacher, you had to demonstrate those things.”

Oswald taught right out of college — her first job was in a classroom on a reservation for the Lakota Sioux in South Dakota.

“I was there for almost five years,” she said. Oswald took a break from the classroom when she started her family. Eventually she was drawn back into education when she was asked by someone in town to serve as the director of Red Brick Nursery School. 

“I went and I loved it. I loved it,” she said. “I was with little kids. You got to see how little kids learned. And you go to see the importance of what was valuable.

“I’ve been so blessed. That’s what is the crack-up. I’ve been so, so blessed to be a teacher and to learn and understand. I learn every single day. Every single day I learn something from these kiddos. It’s so rewarding to me.”

Oswald also appreciates the opportunity to work with so many dedicated teachers.

“I’m only as good as the staff is,” she said. “They give to me every single day too… I have a thing in the class ‘We all shine in so many ways.’ The teachers all shine in so many ways. I enjoy it. It’s fun to be with the other teachers and to see them excited.”

Anderson said Oswald is “all in” as a teacher. Like most Barrington teachers, she dedicates more than just classroom time to the students. 

“We’re a very special group,” Anderson said of the BMS staff. “We put this idea of family and culture and community at the forefront. I think happy teachers will have happy kids. When you think about the middle school it’s everything. It’s the clubs, the opportunities kids have before school and after school and during school, and evenings … and Connie’s there for all of that.”

Anderson said Oswald also leads the newspaper club and community service club. Like many teachers, she will meet students before school for extra help or after dismissal. 

“She chaperones field trips in Washington DC and they’re not even her kids,” Anderson said. “She helps out at Sports Nights. She attends dodgeball and basketball games. We had a student basketball game last year and we couldn’t get Connie off the floor.”

Oswald said she loves being part of the experience.

“A lot of education is data-driven now,” she said. “Data is important, but the connection with students is much more important.”

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