This paper begins by thinking about the meaning of thought itself –together with its tools and enablers. It concludes, that to handle the question of freedom it is necessary to rely on a normative rationality that goes beyond the functionalist reductionism of political reason. It shows how the framework of political reason transforms the question of freedom into a rationalization technique for existing authority. In a second part, the paper focuses on defining the features of this normative rationality, and then goes on to observe the components of a foundational system that might form an objective guarantee for the widest possible scope of freedoms. Looking for a way forward, the paper suggests that the most important component of a discussion of freedom outside this frame is through the ideological and moral impartiality inherent in the rule of law and democracy.