This study examined the process of establishing post homeless lives among 51 recently homeless youth in two major urban centers in Canada. A mixed methods strategy was employed to characterize this process. Quantitatively, a range of mental health, community integration, and quality of life measures were employed four times over the course of 1 year to describe how these indicators of wellbeing shifted in this period. It was found that over the course of 1 year gains were not made in community integration, quality of life and mental health were highly variable, and hope declined significantly. Further, it was found that youth in supported housing arrangements experienced better mental health and community integration. Qualitatively, we identified three major stages in the process of exiting homelessness. These stages included a period of substantial fluctuation and instability, a period of gaining a basic level of stability but being demoralized due to difficulties making progress with life goals, and a period of making some gains with life goals which cultivated a sense of hope. Progress across these stages, which took place in a timeframe considerably longer than 1 year, was characterized by a range of setbacks, individual and systemic challenges, and trauma which were addressed through a persistent effort facilitated by youth resilience and key supports.