This article draws upon the theoretical framework of Pierre Bourdieu to examine the capacity of lower-middle-class young men in Dehradun to gain employment. Despite having tertiary-level education, their search for employment is an extended one, marked by anxiety, hardship and uncertainty, which often precipitates a sense of hopelessness and shame. By utilising qualitative research methods, this article shows how youth contest their marginalisation, for example, by equipping themselves with skills and competencies, or migrating. Despite their attempts, the educated lower-middle-class youth in Dehradun do not possess sufficient stocks of economic, cultural and social capital to consolidate their class position. These findings contribute to debates about the Indian middle classes, social reproduction and neo-liberal development.