Work, paid and unpaid, plays a substantial role in most of our lives. The question the dissertation aims to address is whether, or to what extent, it ought to do so. This question is approached through an analysis of the relationship between work—encompassing both paid market work and unpaid household work—and individual well-being. Assessing the appropriate boundaries of the working day and working life—the amount of work we should allow economic, social, and legal forces to compel—is partly a matter of asking whether work ought to be relied upon to play the various social and political roles we often set for it. The more our lives are taken up with work, the more our chances of living a good life depend on how it goes with us at work—on the opportunities and limitations inherent in both the activity of work and in the dominant institutions in the context of which work is performed. Partly as a function of the amount of time we spend engaged in it, work will play a major role in shaping who we are and can be. There are reasons to believe that work should not be relied upon or required to play such an expansive role. The dissertation challenges widespread, optimistic assumptions about the relationship between work and well-being by exploring the ways in which market and household production can damage or restrict the exercise of capabilities central to human flourishing: work is an unsuitable or unreliable venue for immersing oneself in activities performed for their own sake (autotelic activities); commonly undertaken in contexts that involve dependence on the arbitrary will of another; ill-suited to developing certain capacities that are necessary for active participation in civic life; and can be stultifying with respect to exercises of the power of self-directed choice. The upshot is that we should not be either indifferent to or supportive of the overlapping pressures that give rise to a work-dominated life. Public policy should be oriented towards a greater distribution of “free time”—time in which we have meaningful choices to refrain from paid or unpaid work. An objection echoes throughout the dissertation: namely, that we ought to concentrate on ameliorating the scope for human flourishing within work, rather than limiting the scope of work itself. While there is much we can do to reduce the harms of work as it is at present and the critiques of work elaborated upon are intended to help inform how this might be done and why it should, it is argued that there are limits to how far most work can be transformed so as to be consistent with the promotion of an adequate range of human capabilities. Furthermore, the dissertation highlights the ways in which these two goals can come into conflict, and identifies cases in which we would be better off foregoing some efforts at reshaping the world of market and household work if doing so would enable us to expand the availability of free time.