Messiness and Moxie

A version of this article appears in the spring 2019 issue of STILLPOINT magazine under the title “Vocation as: Messiness and Moxie.”

“Are you serious?” It’s a common response that Karl Simon ’01 gets when he tells people what he does for a living. “This could be, like, one of Mike Rowe’s Dirty Jobs,” says the middle school assistant principal. “I’m not cleaning out sewers, but I’m going into class with seventh grade boys and teaching them sex ed. That takes moxie. That’s a tough crowd.” While many don’t want to relive the awkward, messy years of middle school, Simon sees the sweetness in them. “Middle school is like baking brownies. If you pull them out with 15 minutes left on the oven, they’re all gooey and gross,” Simon explains. But send them off to high school, he continues, “Let them cook for four more years and they are contributing members of society.” “It’s very rare that you pour into a kid’s life and show an immediate return on your investment or an immediate change in behavior,” he says. “It’s delayed gratification—something that you look forward to.” “I love when I hear from former students when they come back from college, or when they text periodically to give me updates,” he says. Some of Simon’s very first students are now teachers and coaches themselves; some are married with their own children. “All of these fun stories come back, but they’re now attached to young adults.” Simon feels a distinct call to serve middle schoolers—and it’s a journey that began when he was, in fact, in middle school. At summer camp, he met Barry Giller, the “cool” camp counselor. Simon instantly looked up to Giller, and over the years that followed, their paths ended up crossing several times—including when Giller led Boston Trinity Academy’s accreditation process while Simon was serving as one of the school’s first teachers and athletic director. And Giller eventually recruited Simon to join the administration at Charlotte Christian School. But it’s not always what Simon had in mind. A communication arts major at Gordon, he planned to go into advertising. “I felt like there wouldn’t be anything more special than to drive down Route 1 or 128 and see a billboard that had a tagline that I thought up on there,” he says. Toward that goal, he participated in the Westmont Urban Semester, where his pursuit of a high-stakes marketing internship led to some soul-searching. He volunteered in an after-school kids’ program and began to realize that “Maybe the corporate world isn’t for me,” he says. “Maybe working with kids is.” “I just get kids—because I still sort of am one,” he says. “Being able to connect my comfort zone into a place that a lot of people would be afraid to go. That’s my vocation.”