This 25-year longitudinal study of a sample of Canadian high school seniors (N = 373) examined pathways from work values at age 18 to mid-life (age 43) career satisfaction and life satisfaction through several possible mediators: age 25 and 32 work values, months of postsecondary education (PSE) by age 25, and age 43 work rewards. Gender and parents’ PSE were also examined as influences on pathways to mid-life satisfaction. Structural equation modeling found support for one pathway beginning with intrinsic work values in high school (age 18 intrinsic work values->age 25 intrinsic work values->age 32 intrinsic work values->age 43 intrinsic work rewards->age 43 career and life satisfaction). Another pathway began with parents’ PSE (parents’ PSE->participants’ age 25 PSE->age 43 intrinsic work rewards->age 43 career and life satisfaction). Extrinsic work values from age 18 to 32 were not related to age 43 work rewards or career and life satisfaction. These findings indicate that adolescent work values matter for important mid-life outcomes, intrinsic work values are stronger predictors of adaptive outcomes than are extrinsic work values, and PSE plays a vital cross-generational role in shaping mid-life satisfaction.