Career adaptability, resiliency and perceived obstacles to career development of adolescent mothers were examined using a proposed conceptual framework that combined resiliency and career adaptability. The goals of this study were to gauge the current state of the career development and resiliency of adolescent mothers, including areas of strength and weakness, and to better understand the interactions between the three components of career adaptability (i.e., planfulness, exploration, decision-making), resiliency and perceived obstacles. Adolescent mothers were similar to nonparenting peers on the planfulness and decision-making dimensions of career adaptability, yet lower on career exploration. While adolescent mothers’ traits of personal resiliency and emotional reactivity were comparable to those of their peers, their relational resiliency was lower. Based on the findings of the study, proposed strategies to further the three components of career adaptability and the resiliency of adolescent mothers are suggested.