This study drew out and described the perceptions of 10 men who successfully made the transition from homelessness to self-sufficiency. Responding to semi-structured openended questions in a one-on-one interview format, participants shared perceptions about their lived-experiences before, during, and after chronic homelessness, and how they navigated the difficult journey to self-sufficiency. The researcher used conventional content analysis to allow the perspectives of participants to emerge from their own words in themes and meaning units. The findings of this study suggest that from participants’ point of view loss of social support due to the death of a parent or spouse, divorce, trauma, substance abuse, physical and mental illness, crime and incarceration are contributing factors to episodes of homelessness. The findings of this study also suggest that obtaining a reliable source of income, personal perseverance, personal faith are important factors related to achieving self-sufficiency. Finally, the findings of this study suggest that coordinated services, the support of trusted individuals, and securing a safe, stable, and encouraging environment provides the needed basis from which to begin the journey out of homelessness