This paper presents constructions of 'work' through a comparative charting of the manner in which young people across rural India, urban India, and the urban UK account for their educational and work trajectories. The comparison grounds an interrogation of the individualisation thesis and the reflexive biography, an influential analytical framework for examining youth biographies in the Global North, bringing it into conversation with theoretical traditions that study youth identities/biographies in a global framework such as development studies and human geography. Employing a conceptual framework that places youth subjectivities as it forms and is formed by place (material and structural features) and cultural norms concerning ideal selfhood, I analyse the accounts for the reflexive management of biographies, the cultural/structural resources that participants draw upon in constructing these, and the moral frameworks underlying aspirations for the 'good life' in these accounts. Responding to calls for dialogues between the Global North and Global South in youth studies, the aim is to de-valorise reflexivity and choice in biographical management by highlighting some psychological penalties associated with these modes of self-construction in late modernity and thereby to 'talk back' to some of the assumptions underlying youth studies in/from the Global North.