Our understanding of the cognitive ambiguities and moral ambivalences surrounding the rationalization of the organizational self has tended to be overly structured by long standing value-laden bi-polar models of organizational culture and associated tripartite schemas of actors and responses. Drawing on a case study analysis of how organizational actors addressed the ambiguities, paradoxes and contradictions surrounding whether planned cultural change was an opportunity for or threat to human freedom, this paper argues for a more open and less-restrictive avenue of research. This alternative involves organizational studies researchers learning more about the intellectual and moral complexity of organizational practice by paying greater attention to the dilemmas facing organizational actors of all kinds seeking to make sense of such ambiguities and grapple with their ambivalence.