This paper examines the predicament of educated youth belonging to socially marginalised groups in realising their aspirations in the city of Delhi. It critically foregrounds the potentials of education and urban location and analyses the educational and employment negotiations and outcomes of the urban youth living at the margins. It is based on a qualitative field study in a settlement predominantly inhabited by Dalits and other backward classes. The paper argues that the local aspirations amid neo-liberal economic expansion in a metropolitan city, alongside the long-cherished dream of respectable jobs, place an enormous hope on pursuing higher education and advanced skills. However, the nature and quality of education and skills that are accessible to these youths hardly enable them realise stable white-collar jobs. Armed with educational degrees, they join and shift between low-end precarious jobs while waiting for stable employment. Gender relations preclude some of these precarious possibilities for female youths who negotiate terms of patriarchal norms to gain economic autonomy. Overall, this paper identifies and elaborates on how urban structural conditions and individual negotiations combine to reproduce social inequalities through a process of socio-economic mobility which is adverse and rarely upwards.