In this presentation I explore the different discourses about the overseas gap year and working holiday that have emerged in the UK and Japan. The comparative perspective of my PhD dissertation allowed an explicit consideration of the influence of socio-cultural factors on the motivations, perceptions, experiences, and outcomes of youth mobility for the young people I interviewed. I highlight how the comparative approach adopted has strengthened the research and facilitated a more rigorous approach to analysis. First, it has required me to explore and specify more precisely the characteristics of working holidaymakers and their positioning within each socio-cultural context. Second, it encouraged a focus not on unelaborated generalities about cultural differences, but on specific factors (e.g., recruitment practices) that may be associated with differences in each context. Third, the research design allowed the identification of important factors in societal discourses in each context, to be used as sensitizing concepts for interviews across contexts. I illustrate these arguments by using preliminary data from interviews conducted in both the UK and Japan.