Efforts to alleviate homelessness and assist homeless men have had varying degrees of success. This variability raises questions about the effectiveness of social policies that guide rehabilitation services aimed at assisting homeless men. Current policy is based on a continuum of care model that includes employment, education, and a social support system as steps toward acquiring self-sufficiency. Literature indicates that few studies have given voice to the experiences and perspectives of homeless men. The purpose of this phenomenological study was to provide the voice of men’s experiences with homelessness and their efforts toward self-sufficiency. The sample included 30 men from the Midwest who were in transition from homelessness to residential stability. The data were collected via interviews and focus groups. Data were analyzed in accordance with a phenomenological approach and open-coding was used resulting in specific categories that emphasized the impact of physical realities, challenges in gaining independence, the role of depression/self-esteem, ineffectiveness of current social policies, a desire to be heard by policy makers, and the usefulness of support systems. Participants consistently reported that current social policies are not adequately linked to homeless men’s personal needs or environmental contexts. Findings from this study inform social change by indicating a clear need for collaboration between policy makers and homeless men in order to create more effective approaches for supporting self-sufficiency. Future directions in this area should include designing, testing, and documenting policy and interventions based on input from homeless men in order to best support homeless men’s efforts toward self-sufficiency.