The aim of this work is to address the obstacles involved in the development of critical and autonomous thinking (free from any and all conditioning) in the midst of organised society and its entire operational structure. To this end, we sought to use as a reference the philosophers Friedrich Nietzsche and Theodor W. Adorno, who share a great deal of similarity in their respective reflections when dealing with the subject. In this way, we seek to focus on the complicated relationship between criticism, society and freedom and, from this point, we try to develop, over the course of four essays, an in-depth reflection on issues relating to social formation, cultural formation and political development from the perspective of both authors, sometimes in dialogue with what we are experiencing in contemporary times.