The impetus for this essay arose from a close reading of the work of American psychoanalyst Hans Loewald. Little referenced in the psychoanalytic literature on organizations, Loewald offers a unique and highly influential set of ideas that both prefigure contemporary psychoanalysis and redefine classical theory. In this essay I explore how Loewald might deepen the psychoanalytic literature on organizations by focusing on his central notion of “replenishing regression.” This notion is placed in dialogue with the prominent paradigm of systems psychodynamics to demonstrate how regression in organizations too often gets cast as a dysfunctional and inhibiting experience to be overcome rather than tolerated and appreciated. By upending this common thinking, Loewald’s work is shown to carry intriguing implications for organizational life, including the prospects of feeling “more alive …though not necessarily the more stable.”