This article examines the impact of economic circumstances on emotional well-being among young adults without a high school diploma in a predominantly Latina/o, urban community. Drawing on the notion of subjective well-being and interview data, the study finds that gendered expectations and parenting significantly affected how the absence of a secondary degree influenced well-being. Whereas "dropout" research focuses primarily on economic outcomes, this article offers a more nuanced picture of the consequences of school failure and argues that, to effectively address the needs of school-leavers, educational researchers, policy makers, and practitioners need deeper understandings of the lives of these young people.