This article explores the imagery and notions of personhood underlying the willingness to undertake extreme work among creative knowledge workers. The core argument is that extreme work is informed by pervasive win-win fantasies which can be recognized in a number of current organizational trends, ranging from New Public Management, over corporate culture, to project work. Each of these trends claims to transcend paradoxes by making contradictory extremes enhance each other rather than hamper each other. This is partly made possible by an increasing immateriality of both money and labor, I argue. Drawing on empirical data from creative knowledge industries, this article illustrates how ‘win-win’ workers subscribe to a set of norms promising that extreme work is a ticket to Never-Never Land. These norms are progression, passion, indispensability, and individual agency. The empirical analysis shows that win-win fantasies imprison us in ‘irreflexive modernity’, unable to escape the dream. In the end, the article discusses avenues for finding our way back into reflexive modernity through moderation, prioritization, and paying critical attention to the deferral between gain and cost practiced in win-win games.