Employing a life span developmental systems perspective, this study used a 5-wave (1985-1992) Canadian longitudinal data set (N = 404) to examine trajectories of intrinsic and extrinsic work values and job entitlement beliefs from age 18 to 25. Piecewise growth models (Slope 1: age 18-20; Slope 2: age 20-25) showed intriguing patterns of change. Unconditional and conditional models suggested downward trends in all 3 measures from age 18 to 20. After age 20, the 2 work values reversed direction. Competing scarcity and value reinforcement hypotheses guided the analysis of change in work values and job entitlement beliefs conditional on unemployment experiences and postsecondary education pathways. Supporting a scarcity hypothesis, more unemployment from age 18 to 20 was associated with a faster increase in intrinsic and extrinsic work values, and a slower decrease in job entitlement beliefs from age 20 to 25. In line with a value reinforcement hypothesis, more unemployment from age 20 to 25 was associated with a slower concurrent increase in intrinsic work values. A postsecondary selection effect was observed; individuals who eventually obtained a university degree had higher intrinsic work values and job entitlement beliefs at age 18. Also congruent with a scarcity hypothesis, young adults with only a high school education experienced a significantly faster increase in extrinsic work values from age 20 to 25. This study highlights the transition to adulthood as a key developmental period for change in work values and beliefs.