This chapter provides an overview of academic debates around the role of structure, culture, and agency in understanding the reproduction of poverty. It is argued that the recent “cultural turn” in poverty studies continues to construct drugs, gangs, violence, and early parenthood as central narratives in the lives of poor black and brown youth, while it privileges middle-class cultural norms. In doing so, scholars ignore the trajectories of youth who continuously struggle to become upwardly mobile. Families, romantic ties, and institutions of school and work function in paradoxical ways in the lives of marginalized youth—providing support while creating impediments as youth are forced to figure out a complex mobility puzzle while piecing together the scant resources available to them. This chapter also highlights how expansion of higher education and the service industry shapes educational and occupational trajectories of marginalized youth. It concludes with a discussion on issues of fieldwork and methodology.