Modern individuality has proven difficult to conceptualize for both modern political thought and contemporary political theory as it appears to contain both a theoretical and practical paradox. If viewed juridically (as bearers of rights) or economically (as bearers of interests), individuals appear abstractly equivalent, non-particular, and even atomized. Yet, as human beings and political agents, individuals are also understood as non-fungible, concretely embodied, and socially-embedded in numerous particular relations. These assessments are not simply different descriptions but rather two opposed sides of that which the concept “individuality” purports to grasp: actually-living individuals. However, political theory has largely explained this discursive divergence as the product of either conceptual imprecision and confusion, or as an aporia between conflicting normative evaluations of individualism. Rarely, however, has the contradictory character of individuality been theorized as the reflection of a specific social-historical form of individuality produced by socioeconomic conditions and institutions which are in themselves contradictory. In other words, the contradictions of the concept of individuality point to contradictory social forms in which we confront ourselves as actually-living individuals. In the following, I argue that the contradictory form of individuality is both inherent to and a reflection of the objectified forms of social relations unique to modern capitalist society. Through a critical analysis of these forms, I show that the growth of capitalist social relations has historically supported the development of modern individuality. Yet, at the same time, these relations have also eroded the conditions for individuality as an anthropological type and threatened actually-living individuals with liquidation. While some sociologists have theorized the emergence of modern individuality and its subsequent decline as a paradox of individualization and de-individualization that follows a linear historical development, I argue that this paradox inheres in the very form of individuality as the expression of social relations which have become autonomous of human beings. By investigating how economic institutions constitute a specific form of individuality that is paradoxically self-undermining yet potentially emancipating, my dissertation suggests that for contemporary political theory to analytically and normatively explain what it purports to grasp, it must also engage the perspective of a critical social theory of prevailing socio-economic conditions. Specifically, I locate the crux of the contradiction of individuality in the institution of waged-labor. Evidenced by mass unemployment in the global South and chronic underemployment and the growing precariousness of work in more developed countries like the United States, the ongoing crisis of work indicates that although capitalist development has undergirded the emergence of individuality as we currently understand it, individuals are at the same time made increasingly superfluous for capital’s self-reproduction. Moreover, I argue that overcoming this crisis is germane to the aspiration for a free individuality that unifies an otherwise diverse liberal tradition. However, for the potentially free individual to be realized would necessitate a radical transformation of social conditions—hitherto undertheorized by much of liberal thought—including the abolition of waged-work and the social reorganization of time.