This article, based on a case study, develops a psychoanalytical understanding of workers’ contradictory psychodynamics in post-bureaucratic organizations. While the managerial language in our case insists on “freedom and happiness” at work, “liberation of energies”, critical perspectives on such organizational trends insist on individuals’ seduction, subjectification and sub-jugation, or work intensification. Previous research (Dey & Lehner, 2017; Maravelias, 2003; Vallas, 2006) critiques such dichotomy. By drawing on Lacan our case study offers a broader account of the ambivalent interplay between managerial language, new post bureaucratic organization and psychodynamics. Particularly, workers experience both the contradictory psychodynamics of enthusiastic engagement and disarray. We suggest a possible interpretation with the notion of “fantasy” as developed by Žižek (1989, 1997, 1998) after Lacan. Fantasy allows accounting for how individuals invest enthusiastically in such a managerial language of “freedom, liberation of energies and happiness at work”, and it also unveils how such psychodynamics lead to disarray. We also link these effects to the weakening of the symbolic order (Vidaillet & Gamot, 2015).