This article uses the concepts of ‘transnational social fields’ and ‘habitus’ to explore the multifaceted role families play in shaping the aspirations of onward migrating youth. The article draws on biographical life history interviews conducted with the children of Iranian migrants who were raised in Sweden but moved to London, UK as adults. The findings of the study suggest that from a young age, all the participants were pressured by their parents to perform well academically, and to achieve high level careers. These goals were easier to achieve in London than in Sweden for several reasons. Interestingly, however, participants’ understandings of what constituted success and their motivations for onward migration were nuanced and varied considerably by gender. The study contributes to an understanding of the role of multi-sited transnational social fields in shaping the aspirations of migrant youths, as well as the strategies taken up by these migrants to achieve their goals.