Modern liberal society is understood to be a functional organisation that is predicated on upholding the principles of individuals’ liberty (understood as freedoms) and equality (before the law) through the organisational principle of natural liberty (a self-regulated system or spontaneous order). In this chapter we trace back these ideas to the origins of liberalism to find that there is no justification for them, there. Instead, we argue that whatever individuals seek to achieve either by forming society or by creating institutions that will promote certain expectations which they may have from it, there will always be a price in terms of that which people believe that they already possess or have a right to possess that is independent of social existence in the former case or the new institutions in the latter. We argue here that whether one takes the view of a social contract or one sees society as a natural phenomenon where social bonds may have preceded the emergence of the conception of the self, the idea that individuals’ freedoms coupled with an organisation based on natural liberty cannot be the raison d’être of social organisation. This is particularly so when we take into consideration that natural liberty will always fail to deliver that which people may expect from the social project.