The central focus of this essay is Isaiah Berlin’s arguments about the concepts of negative freedom and positive freedom, developed in his philosophical work Two Concepts of Liberty. By adopting a philosophical standpoint, this essay explores the application of Berlin’s notions of freedom at the organizational level, within the workplace, and in the management field. This essay presents three philosophical arguments that provide some clarifications about the potential challenges associated with autonomy in organizations. These arguments incorporate Berlin’s ideas of freedom (...) with philosophical insights from Heidegger, Sartre, Frankfurt, and Confucius to highlight the missing elements of autonomy in management literature and its implementation in organizations, explaining the challenges of autonomy and the reasons for some unexpected results. Recommendations for future studies and managerial implications are discussed. (shrink)