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Purpose – Research finds that youths who are able to align their educational and occupational ambitions are better able to realize both. In this chapter, we describe when and how the educational, occupational, and family aspirations and expectations of a subgroup of youth often marginalized in traditional status attainment research are aligned.

Methodology/approach – We use qualitative data from the Gautreaux Two program in Chicago, which gave vouchers to families in existing public housing to move to low-poverty and racially diverse areas. Our sample includes in-depth qualitative interviews with 93 children in 57 of the families included in the study.

Findings – Our results show that there are two groups of youths – one group whose educational, family, and occupational ambitions are aligned and one whose ambitions are misaligned. Many of the narratives of the youths whose ambitions are at odds reflect the ways in which competing ideologies of success for inner-city children can lead to misaligned aspirations. Both groups of youths also discuss their awareness of the difficulties they face in realizing even their aligned ambitions.

Research limitations/implications – This research provides implications for policies and programs seeking to improve youths' experiences both in housing mobility programs and disadvantaged neighborhoods and schools.

Originality/value of paper – This chapter adds to previous research by considering how youths' family plans intersect with their educational and occupational ambitions. Also, we explore the alignment of ambitions among a group of youths who may be considered socially marginalized, those who have grown up in urban housing developments.