Increasing numbers of low-income and minority youth are now pursuing shorter-duration sub-baccalaureate credentials at for-profit trade and technical schools. However, many students drop out of these schools, leaving with large debts and few job prospects. Despite these dismal outcomes, we know very little about students’ experiences in for-profit programs and how these institutions shape postsecondary attainment. Using data from fieldwork with 150 inner-city African American youth, we examine why disadvantaged youth are attracted to these schools and why they struggle to complete certifications. In contrast to previous research, we find that the youth in our study have quite modest ambitions and look to for-profit trade schools as the quickest and most direct route to work. However, youth receive little information or guidance to support such postsecondary transitions. Therefore, the very element that makes for-profit trade school programs seem the most appealing—a curriculum focused on one particular career—becomes an obstacle when it requires youth to commit to a program of study before they have explored their interests. When youth realize they do not like or are not prepared for their chosen career, they adopt coping strategies that keep them in school but swirling between programs, rather than accumulating any credentials.