Abstract: The point of departure for this dissertation is the arguably radical claim made by Pope John Paul II in his 1981 encyclical Laborem Exercens (On Human Work) that human work is 'the key, maybe the essential key to the social question.' My interest is in unpacking the meaning of this statement through an analysis of the underlying anthropological framework presupposed by John Paul and grounded in his work as the philosopher Karol Wojtyla. I then question the adequacy of that framework by comparing it to the anthropology of Bernard Lonergan. My intention is to determine which understanding of the human person in the act of self-transcendence provides a more adequate basis for John Paul's claim, and which allows for a more comprehensive grasp of the role that human work may play in living a Christian life. John Paul grounds this statement in a distinction between what he refers to as the two dimensions of human work. The first, the objective dimension, is concerned with the external results of work, the product or service produced by the worker, whether that be in the public or private sphere. The second, the subjective dimension, is concerned with the inner results of work, with its impact on the dignity of the human person and his or her own capacity for personal becoming and full human flourishing. The dissertation is directed toward a more comprehensive understanding of the subjective dimension of human work, with the ultimate objective of establishing the philosophical and theological foundations of how one becomes 'more of a human being' through the work that we do. But the Pope's own statements point to, not work perse as the key to the social question, but to a process of conversion that is made possible through work. Hence, I argue that it is an understanding of this phenomenon that will provide the essential key to the social question and my concern is to determine whose theory of self-transcendence, that is, conversion, is more adequate to the task. This argument is further grounded in Lonergan's conviction that the new foundation of theology must be reflection on conversion. After establishing the theological and historical context of conversion and of work, I compare these two philosopher-theologians in three areas: the place of the historical human person in their respective projects, their understanding of how one comes to know the good, and, finally, their theories of self-transcendence. While affirming the important contribution made by Wojtyla to the tradition, especially in light of his attempt to synthesize Thomist metaphysics with phenomenological method, I conclude that Lonergan's system provides a more adequate foundation for the question at stake here. His cognitional theory allows for the ontological realism so important in the concrete world of work, and his theory of conversion is more comprehensive and accessible to those facing the challenge of integrating their work with their Christian faith.