The present article describes a two-year longitudinal study of two "at-risk" US teenagers who successfully transformed their unusually challenging high school experiences into motivation to become classroom teachers. Frank's adolescence was characterized by addiction and defiance. He spent his sophomore year in a locked, residential treatment center, and his junior and senior years in a therapeutic boarding school. Marie spent 19?months in a residential school for adolescents with substance abuse problems, becoming pregnant the following year. At age 22 both Frank and Marie graduated "summa cum laude" (grade point average of 3.9 or greater) from the same nationally recognized teacher preparation program. The archetype of the "wounded healer" is used to interpret their experiences. Results suggest (1) memories of personal adversity in school may have a profound impact on an individual's orientation to teaching, and (2) these memories can be used advantageously by pre-service teachers. Implications for teacher educators are discussed.