This thesis undertakes a philosophical examination of three figures at the heart of post-bureaucratic thought – the figures of the creative manager, the authentic leader and the entrepreneur. While the figures of the creative manager, the authentic leader and the entrepreneur share the aim of resolving the crisis of Taylorism, this thesis argues that they produce their own internal crises. They do so because the figures of the creative manager, the authentic leader and the entrepreneur are inherently bound to concepts that resist transmutation into a managerial logic that would enable them to serve their functional purposes without betraying their conceptual dynamics. What philosophy offers us is not a ready-made solution to the crises of the creative manager, the authentic leader and the entrepreneur, but rather a point of departure for constructing concepts that enable us to explore the paradoxes embedded within these figures. Since philosophical concepts dwell in crisis, they enable the thesis to capture the paradoxes, aporias and impossibilities that inevitably accompany post-bureaucratic thought. Instead of regarding the crises in post-bureaucratic management thinking as an impasse, abyss or deadlock, the thesis shows how they can chart new ways of conceptualizing the postbureaucratic organization. Drawing on Derrida’s concept of pharmakon, Deleuze’s concept of simulacrum and Zizek’s concept of fantasy, three concepts equally marked by their paradoxical nature, this thesis opens up a philosophical critique of the post-bureaucratic image of thought. This will be done by exploring the figure of the creative manager through a reading of Gary Hamel’s popular management handbook The Future of Management informed by Derrida’s concept of pharmakon; the figure of the authentic leader through a reading of Bill George’s semiautobiographic self-help tome Authentic Leadership informed by Deleuze’s concept of simulacrum; and the figure of the entrepreneur through a reading of Richard Branson’s autobiography Losing My Virginity informed by Zizek’s concept of fantasy.