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The purpose of the present study was to examine the longitudinal relationships between planned happenstance skills (PHS) and life adjustment and to examine whether this relationship was moderated by the degree of career barriers. The participants were 307 Korean college students going through a school-to-work transition. The results showed that PHS preceded and were positively associated with life adjustment. Additionally, the association between PHS and life adjustment differed by the levels of career barriers; individuals with greater PHS were more likely to adjust well in life even when they perceived high career barriers. The findings suggest empirical support for planned happenstance theory. Implications regarding career counseling interventions for college students in a school-to-work transition are discussed.