The purpose of this paper is to rethink the topic of freedom for contemporary psychology. Freedom, within psychological research today, is a neglected, even slightly old-fashioned term. In this paper, we explore the practical, normative, and political dimensions of freedom as a psychological concept. We begin by tracing out key understandings of freedom from political theory, before discussing how thinkers such as Skinner, Maslow, Fromm, and May understood the different dimensions of freedom. We then discuss a governmental perspective on freedom, drawn from the work of Nikolas Rose, before finally turning to the sociocultural psychology of L. S. Vygotsky. We contend that freedom is not merely the absence of constraints but a complex interplay between agency, responsibility, and social connections. Our paper argues that the modern emphasis on negative freedom, characterized by reduced interference and obligations, has resulted in a paradoxical situation where individuals feel overwhelmed and seek escape from freedom. By revisiting the insights of Erich Fromm and other scholars, we emphasize the need for positive freedom, which involves voluntary connections with others and active participation in shaping society. We argue that psychology’s mandate should be to facilitate the exploration of alternative avenues that lead to flourishing and self-actualization.