Youth between the ages of 18-21 leaving the foster care system typically face poor outcomes when transitioning into adulthood. This “aging-out” population encounters many challenges, including lack of adult support, financial instability, poor educational/vocational opportunities and outcomes, and lack of safe and affordable housing. Older youth exiting the foster care system are more likely to experience unplanned pregnancy, unemployment, criminal justice involvement and substance use. Additionally, youth who have been in foster care are at increased risk for behavioral and mental health difficulties after leaving foster care (Courtney el al., 2007; Stein, 2006; Freundlich & Avery, 2008). Yet, despite the preponderance of evidence for poor outcomes and the seemingly insurmountable challenges faced by this population, a number of youth leave the foster care system and are able to lead satisfying, productive lives. This qualitative study used intensive interviews to explore the trajectory of a small number of youth who have transitioned out of foster care, outlining the social, economic and psychological barriers they faced while also charting the attitudes, behaviors and experiences that allowed them to successfully exit the foster care system and move toward productive adult lives. Results of the study suggest that successes among this population are hard-won and tenuous. Ultimately the youth in this study were able to overcome obstacles and navigate the transition to adulthood by tapping both internal strengths and external resources, including the ability to reconcile and move beyond disappointments, connect with others, and take advantage of available sources of support.