This chapter explores the dilemmas of the career logic driven by individual competition, within a family-friendly welfare state. Drawing on quantitative and qualitative data on mothers and fathers in Norwegian elite professions, the chapter shows that family-unfriendly expectations requiring limitless time, flexibility and energy are indeed present – especially in the private sector and at higher career levels. These demands are not experienced as originating from unreasonable employers but from the never-ending competition for projects and clients. Although both mothers and fathers face these expectations, it is typically mothers who bear the consequences and find a position with reduced pressure at lower career levels in the public sector. The chapter discusses the dilemmas of optional family-friendly facilitation: As long as other players are able and willing to invest in the career game, setting limits for work may also imply limiting one’s own future career. Thus, the potential for changing the trump cards of time, flexibility and energy might be limited. However, a more gender-equal division of family responsibility (including parental leave and other family-friendly policies) may change the division of trump cards and perhaps alter the rules of the career game for the future.