Chronically homeless individuals, or Street Dwellers, present unique challenges for clinicians and outreach workers who engage them when offering services like food, shelter, clothing, healthcare and mental health counseling including substance abuse treatment. This study examines Street Dwellers' hopes, dreams and aspirations for a better life. Through thematic analysis of interview statements five themes emerged; Normal Life, Optimism, Planning, Helping Others, and From Rags to Respect. Study findings suggest that Street Dwellers dream vividly and often about a life off the streets while frequently forming and reforming plans to get there. These findings provide clinicians and outreach workers insight into the phenomenon of Street Dwelling that could be used to design more effective strategies to help this vulnerable population.