Research shows that young adults (ages 16-25) with serious mental health conditions struggle to succeed in school, training, and work compared to their peers with other or no disabilities. However, these findings are based on research that has been cross-sectional in nature and lacking first-person narratives from young adults themselves. Life course perspectives and Social Cognitive Career Theory emphasize the dynamic role of individual and contextual circumstances and experiences over the life course on career development and the experience of managing a mental health condition. Utilizing life history interviews with fifty-five young adults (ages 25-30) with serious mental health conditions, this dissertation describes their patterns of school, training, and work activities over time and identifies the barriers and facilitators to success. This dissertation also identifies and explores individual experiences of managing a mental health condition, social-contextual factors that are influential on young adulthood, and how young adults perceive themselves and their experiences. Overall, post-secondary patterns of school, training, and work were non-linear and mirrored erratic patterns of interactions with the mental health treatment system that involved multiple diagnoses, medications, and hospitalizations. Many young adults had impoverished career trajectories and challenges associated with mental health were the most frequently reported barriers to school, training and work. Common facilitators to success included flexibility and support within school, training, and work environments. Adverse childhood experiences, including parental mental illness, were common and perceived as having long-lasting negative impacts on mental health and later social relationships. Perceptions of mental illness were varied but overall young adults in this study benefited from several intrinsic benefits of working and going to school. This exploratory study has implications for practice and future research.