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This paper explores how the individual values of self‐direction, power, and benevolence predict career decisions (self‐ or paid employment). By observing heterogeneity in career patterns across countries, this research examines the moderating effect of cultural contexts (gender egalitarianism, performance orientation, and collectivism) on this relationship. Blending the theory of human values (THVs) and institutional theory (IT), we test hypotheses using the World Values Survey (WVS) Wave 6 data and GLOBE cultural dimensions from 21,286 individuals in 26 countries. The findings show that only self‐direction value increases the likelihood of being self‐employed. However, the post‐hoc analysis offers more insightful findings: the decision towards innovative entrepreneurship instead of routine self‐employment is explained by all values of self‐direction, power, and benevolence, together with individualistic culture. Overall, this study finds that the influence of individual values is greater than cultural context on career choice and it differs between self‐ versus paid employment and innovative entrepreneurship versus routine self‐employment. [ABSTRACT FROM AUTHOR]