This thesis is a study of three philosophical formations in the long and colourful history of melancholy as a cultural notion. For nearly two millennia the notion of melancholy helped to shape, organize, explain, focus and render manageable the encounter between individual and collective in the Western world. In terms of its implications for social, ethical, epistemological and medical norms, the multiplicity and diversity of this history is with-out comparison in the Occident. Yet, the work presented here is not so much an attempt to unravel its historical complexities. Rather, it is an effort to show that the history of melancholy can provide an unequalled and vital background to a philosophical study of the relations between the contemporary modes of organizing work and the individual pathos of work-related illness like stress and depression, which today has assumed a central role in the way we understand the partaking in a socioeconomic reality. In this sense, what the thesis provides is philosophical groundwork. It offers a looking glass through which the fascinating history of great achievement and personal failure that is central to the category of melancholy can be represented in all its foreignness, and yet, at the same time, can be said to reflect and illuminate the present. The philosophical formations explored here, it is my hope, can lead to a better and more complex understanding of the association in the contemporary between work-related illness and the injunction to participate and contribute as a self in the modern organization. What they provide is an attempt to inform and speak into the present from the point of view of history; not in order to reach the sublation of now and then, but in order to illustrate how philosophy, and the reflexive-hermeneutic space that it opens, persist in making us the contemporaries of a past that remains negotiable and precarious.