Complementing existing research that has investigated the reciprocal effects between individuals’ personality traits and occupational choices, we move from a variable-centered to a person-centered approach and examine the interplay between combinations of personality traits and individuals’ occupations. Leveraging German panel data tracing individuals’ career trajectories from 2005 to 2017, we utilize a distance-based methodological approach from the spatial sciences to measure and relate similarities in individuals’ overall personality traits and similarities in their occupations. We find that individuals with similar Big Five personality traits enter similar occupations and that individuals with occupation-specific personalities are more likely to stay in the occupation. Moreover, we show that working in similar occupations contributes to the convergence of personalities over time. This research enhances our understanding of the intricate interplay between personality and occupations, providing a comprehensive and innovative test of attraction and selection, attrition, as well as socialization effects between more similar individuals and occupations.