Carolyn Pless was a teacher of young children for 30 years, teaching first at Duffield School, then East Side, and later at Lynn Avenue and Harold McCormick School. Lilo Duncan, Carolyn’s best friend and a lifelong friend, recalls that Carolyn had not yet graduated from college, when T.A. Dugger, Jr., then superintendent of schools, hired her to fill in for a teacher at Duffield School, who was taking a leave of absence. “That summer she went back to school and got her teaching degree, and the next year she was given a position at East Side School. She had 43 first-graders!,” said Lilo. She then taught at Lynn Avenue until it closed, and finished her career up at Harold McCormick.