This mixed-methods, context-oriented study explored transitions to motherhood among pregnant and newly parenting inner-city teenagers (n= 80) attending an alternative public school. Additionally, a novel research approach was assessed. Using data from a 2-year psychotherapy trial, inductive content analyses of therapy sessions and post hoc interviews of clinicians were synthesized with questionnaires and other more traditional data sources to develop a strength-focused understanding of prominent life themes, as experienced by participants. Results suggested that, although few teens had planned to have a baby, a large majority were pleased to discover their pregnancies. A heightened sense of purpose emerged, connected with drastically increased safety-conscious behaviors. Still, public and familial alienation was common. Grandmothers and additional female mentors became central, and their support of the pregnancy was protective against teen mothers' depression. The research technique assessed in this study provided broad-ranging information with substantial validity and minimal time and expense.