Academic research and mainstream media have raised concerns about the damage individuals exhibiting narcissistic, Machiavellian, and psychopathic tendencies create in organizational settings. As such, understanding where these individuals are likely to seek employment is critical to the proper management of organizations. To clarify these relationships and inform managers on where these individuals are likely to seek employment, we extracted relationships among the D3 traits and RIASEC interests from 32 independent samples (N = 13,679) from 2001 to 2023. Our results demonstrate that all three traits are strongly drawn toward enterprising professions and that Machiavellians and psychopaths are repelled by social vocations, suggesting that individuals with these traits are drawn to roles that allow them to exert influence over others, but their attitudes toward social interactions differ. Subgroup analyses on methodological factors indicated that published journal articles, online panels, and brief unidimensional measures of the D3 traits tend to skew effect sizes. Moderator analyses also showed a gender difference in some Machiavellianism and psychopathy effects but no notable differences in narcissism effects. The results largely suggest that the RIASEC framework may be too abstract to investigate these relationships completely and that unidimensional conceptualizations of the D3 traits may obscure underlying variations in these relationships. Overall, this research contributes to the broader understanding of the intricate interplay between personality traits and career choices and serves as a foundation for more nuanced future investigations.