This chapter explores the philosophy of Gilles Deleuze as a source of insight for understanding the complexity and precariousness of organizational life. Deleuze’s work consistently resists representational models of thought, instead emphasizing how sense, meaning, and reality are actively produced in events, encounters, and practices. His early reading of Nietzsche reinterprets the ‘will to power’ as the dynamic interplay of forces that continually shape values and perspectives, offering a dynamic framework for understanding how meaning emerges. Building on this, in his later work, Deleuze develops a philosophy of events and sense that challenges static models of order. Sense is understood not as fixed meaning but as a pure event that shifts relations and opens new possibilities. Deleuze’s later collaboration with Félix Guattari extends this perspective through the notion of desire as a productive force, operating through assemblages of desiring-machines that connect bodies, institutions, and practices. Desire is not lack but generative flow, shaping both social reality and organizational forms. Finally, Deleuze’s engagement with Leibniz introduces a powerful metaphor for sensemaking: organizational life as layered, curved, and perpetually unfolding. Together, these concepts provide a nomadic philosophy of sensemaking—one that reframes organization as an open-ended, dynamic, and transformative process.