Many studies have examined the effect of life events, education, and income on well-being. Conversely, research concerning well-being as a predictor of life course outcomes is sparse. Diener's suggestion "to inquire about the effects of well-being on future behavior and success" has, with some exceptions, not yet come to fruition. This article contributes to this body of research. We conceptualize and analyze the interplay between educational achievement, occupational success, and well-being as a complex process. The relationship between these domains is examined drawing on a structure-agency framework derived from Bourdieu and Social Comparison Theory. Social comparison between adolescents and their parents is suggested to be the mechanism explaining the effects of successful and unsuccessful intergenerational transmission of educational achievement and occupational success on well-being. It is further argued that well-being may serve as an individual resource by fostering educational and occupational outcomes. Panel data from the Transition from Education to Employment (TREE) project, a Swiss PISA 2000 follow-up study, was used. The interplay between well-being and successful and unsuccessful intergenerational transfer of educational attainment was analyzed in an autoregressive cross-lagged mixture model framework. Social comparison was found to be related to well-being, while well-being proved to significantly increase the probability of successful intergenerational transfer of educational attainment.