This article explores in the relationship between the concepts of liberty and constituent power, applicable to contexts of constitutional change in the contemporary world. Using a philosophically skeptical approach to the concept of liberty, the paper provides a reflection on the meaning of political liberty as applied to our everyday social interaction. In line with some of the traditions of classical and early modern thought, this work outlines the link between constituent power and liberty as a complicated relationship. As will be argued, it is not plausible to identify sovereign instances of political interaction as moments of full autonomy to establish long-term normative guidelines within a society. Contrary to what might be thought, however, the awareness of relative political liberty is a central element in the politically emancipatory performance of constitutional power.