To construct a career is a complex developmental task that involves several contextual and personal factors. The uncertainty and instability that characterise modern societies are evident in many European countries. The present study aimed to explore the processes of career development and meaning-making, and how cultural and contextual factors may affect students' career choices and development. Twenty-one Italian and 20 English first-year university students produced written narratives inspired by the same prompt. Findings confirm differences in career development and choices linked to the effect of contextual factors and to different life story trajectories.