Wendy Cogswell is best known on campus for her smiling face as she ushers students across the road for All-School Meeting and her cameo appearance in last fall’s Grasshopper Night, but Officer Wendy, as she is often called by students, believes she was destined to be a teacher.

Cogswell, the Community Relations Officer for Phillips Academy Public Safety (PAPS), grew up in Tewksbury, MA, a neighboring town of Andover. Her mother was a teacher. “I was very influenced by education,”...