This study investigated the extent to which tolerance of uncertainty affects the relationship between happenstance skills and career satisfaction via career decision self‐efficacy. Moderated mediation analysis was conducted on data collected from 321 graduates (175 men, 146 women) of Korean universities making the school‐to‐work transition. Results showed that career decision self‐efficacy fully mediated the relationship between happenstance skills and career satisfaction. Furthermore, the moderation effect of tolerance of uncertainty had a significant impact on the relationship between happenstance skills and career decision self‐efficacy. Tolerance of uncertainty should be considered an important variable in happenstance career theory and intervention. Unplanned influences should also be considered important factors in the career decision‐making process.