The article applies evolutionary theory to the concept of career success, to argue the primacy of ‘objective’ outcomes, utilities such as status and wealth, and to analyze why the relationship with subjective career success is not stronger. Although there are grounds for expecting subjective evaluations to be sympathetic secondary accompaniments of objective success and failure, there are substantial numbers of paradoxically ‘happy losers’ and ‘unhappy winners’ in the career game. These are explored theoretically as adaptive outcomes of self-regulation and sense-making processes. The nature of that game is then explored by a closer examination of the interrelations and decay functions of the major objective success outcomes. This is undertaken as a theoretical exercise, and also by reference to the evidence in the literature. Both approaches support the existence of close linkages among most of these outcomes, though empirical data reveal variations that highlight the importance for careerists to be aware of trade-offs and risks in career strategies. Context mediates these relationships, especially key contingencies such as individual differences, gender, career stage, culture, and business sector. The implications are discussed; in particular the role of careers theory and research in helping to cut through some of the ideological aspects of ‘subjective’ careers in order to help raise the awareness of actors in the labor market about objective career realities. Copyright © 2005 John Wiley & Sons, Ltd.