Schools are often criticized for their role in creating the dropout problem. This article illustrates that with the right resources and approach, educational programs could become sites of transformation rather than reproducers of social inequality. Narrative and thematic analysis of in-depth interviews with graduates of a nationwide program that serves high school dropouts reveals that its asset-based, mission-driven approach touched many aspects of these students' lives and produced changes in elements of their habitus. Aspects of the program that appeared to be central in changing participants' habitus include the development of self-esteem, the ability to accomplish something of value, and the capacity to contribute to the welfare of others. Implications of these findings for influencing the habitus of school dropouts and improving upward social mobility are discussed. (Contains 8 notes and 2 tables.)