The mobility of highly skilled individuals between EU/EFTA countries is often discussed as either about choice and professional careers or about overqualification and power relations that lead to deskilling. To highlight these issues’ entanglements, this paper draws on in-depth interviews with tertiary-educated Spaniards who migrated to Switzerland for work. Using Bourdieu’s capital approach, we unpack the generic definition of “qualification and skills mismatch”, which is a key issue in young highly skilled migrants’ labour market experiences. In so doing, we reveal the very individual and nuanced meanings of qualification and skills mismatch, including often subtle constraints in the labour market and personal limits imposed by accepting mismatching work arrangements. We thus contribute to the understanding of migration, work experiences, and aspirations in the course of middling transnationalism. Our respondents see mobility both as a phase of freedom with the opportunity to gain experience abroad and one of critical periods and uncertainty in relation to work opportunities. The respondents also perceive themselves as still in transition from higher education to work, and in some cases they see global work experience as a form of capital that can improve their work opportunities in Spain as much as in other countries. We argue that these perceptions help them to cope with periods of uncertainty in the context of work.