Even as federal policymakers debate the reauthorization of Temporary Assistance for Needy Families (TANF) legislation, state-level activists are beginning to discuss the best ways to implement the policy in their locales. The District of Columbia has experienced the lowest reduction in percentage of welfare caseloads in the country since the 1996 welfare reauthorization. This study explores implementation of welfare policy that both facilitates and hinders the ability of DC welfare clients to become self-sufficient. The study features in-depth interviews with twenty-six welfare clients in the District to add individual voices to the quantitative data gathered on the topic. Specifically, this paper explores the context of welfare clients' lives before and once on welfare, and asks which welfare policies they perceive to be obstacles to their own self-sufficiency. A limited ability to save money, few childcare options, strict transportation and job search requirements, and poor relationships with caseworkers all hinder a client's ability to support herself without assistance from TANF. A qualitative analysis will show that welfare recipients want and are ready to be self sufficient and have clear ideas of the current barriers embedded within the welfare systems that make their personal escape from poverty more difficult.