Henrico's Top Teachers – Sheila Olesen, Saint Mary's Catholic School, math

The teaching bloodlines run deep in Sheila Olesen's family.

So naturally, it was the last thing she wanted to do.

“I was trying to go against the grain for a long time,” she said with a laugh. “It was in my blood, so I didn't want to do it.”

Olesen tried to avoid her fate by entering the field of social work, then spending time in the Navy. Eventually, though, the bug bit her, just as it had her mother (the first integrated school teacher in Annapolis, Maryland) and her grandmother, a longtime special education teacher.

She began teaching in her late 20s in Annapolis, then moved to San Diego and taught there, took about seven years off from the profession to become a mother, and has spent the past decade teaching math at Saint Mary's Catholic School, a private school in Henrico's West End.

Just as teaching didn't seem to be in the cards for Olesen earlier in her life, math never would have registered as the subject she'd teach once she finally did enter the profession, either. She didn't particularly care for math as a student herself but had to teach it by default as a rookie teacher, so she worked to figure out ways to make it interesting for her students.

A quarter-century later, her enthusiastic and creative ways to engage students have become a hallmark of her classroom legacy.

“I wouldn't have thought that learning math could be loud, but it is when you have Mrs. Olesen,” wrote a coworker and nominator. “She just can't seem to contain her excitement, which is clearly contagious and spills over daily into eagerly engaged students. I have learned to bring headphones to work when I need to focus, but I rarely use them because I don't want to miss out on the sounds of happy learning. Even through the wall, she has me hooked too!”

What would a younger version of Olesen have thought upon learning that she'd be teaching the subject for years?

“That something went wrong,” she said with a chuckle. “I wouldn't have seen that coming.”

Now, it's her students who stay on their feet, never knowing what might be coming next from Olesen.

She celebrates pi day each year with her classes, uses hula hoops in class and does whatever else she can to develop connections with her students. She values the smaller class sizes at Saint Mary's, which she said allow her simply to teach and help students learn rather than worrying about how they will perform on a standardized test.

“If you asked my kids, there’s a bit of a theme over 25 years,” she said. “I’m that person who's not too scared to dress up like a ninja warrior to teach fractions. I want to let them know they can learn math, and it can be fun.”

Olesen teaches third- through fifth-graders who qualify for her enrichment classes and also teaches on-grade-level middle school students. As a former soccer player and gymnast, and the mom to two athletes, she often uses sports analogies and lessons to connect with her students.

“What you overcome, how you have to try harder, [that] setbacks are the best things to learn from – the laws of sports are the same as the laws of learning anything,” she said.

Her impact on the school – inside and outside the classroom – is evident to those around her. As a regular helped in the school's front carpool line, she's one of the first people students and parents see each day and one of the last they see in the afternoons. She's organized Christmas and end-of-school-year sendoff celebrations for students, “to make more of a mark” and help students celebrate endings and new beginnings.

"I’ve seen first hand how she can take an average math student and make them want to excel because they don’t want to miss her class and cannot help but pay attention to her dynamic lessons," a nominator wrote. "Most importantly, I get to see the self confidence she imparts on all of her students; regardless of their grades or individual aptitude.
 Sometimes gifted math students are less gifted than others with their social skills. This is an area where Sheila shines. She connects with these learners on what seems like a molecular level. It’s as if she can see inside their minds and understands not just how to teach them, but also how to relate to what and how they feel on a daily basis.
 Combine this with her background in social work, and it should be no surprise that her classroom has become a safe space during moments of the day when she is not teaching."

Several years ago, Olesen was wearing a St. Christopher's School button and a parent jokingly asked her why she didn't have any Benedictine gear. Two parents bought her hats, then others gave her hats from Collegiate and Trinity Episcopal. Now, she's known for routinely wearing any number of different hats to represent schools attended by Saint Mary's alumni.

“She shows no favoritism or rivalry, proudly donning the badges of public, private and Catholic schools, all with equal pride,” a nominator wrote. “It's just one of many small ways she maintains a connection with current and former students.”

Olesen is leaving the classroom after this school year – perhaps just as a temporary 'gap year,' she joked – to spend more time with her twin sons, who will be high school seniors next year.

But she realizes it will be tough to keep her away from school after that.

“I love the classroom,” she said. “I love it.”