Psychocentrism is a governing neoliberal rationality that pathologizes human problems and frames individuals as responsible for socially structured inequalities. The homeless community provides an important case study to examine the ways psychocentrism manifests among an excluded population. This paper explores the paradox whereby homeless individuals are simultaneously pathologized and responsibilized through psychocentric discourses in which their status as economically poor becomes individualized as a symptom of mental illness and/or addiction. Although medicalized understandings of mental and emotional distress pervade the homeless industry, the obligations of freedom in the neoliberal era mean that individuals alone are held responsible for their failures. The paper examines the ways individuals experiencing homelessness are compelled to embark on an entrepreneurial project of the self that requires them to accept blame for their social precariousness. Further, it deconstructs the narratives that regard social explanations as an excuse and a failure of individual accountability. I argue that the “shamed poor” adopt empowerment discourses touted by the homeless industry, which paradoxically encourage individuals to find strength in their personal failures and to work toward self-governance, devoid of historical, social, and cultural context.