There is a clear tension in the neoliberal approach to individualism and freedom. Focusing on the process of individualization and individual self-determination in markets, neoclassical approaches recognize that individuals are committed to social mobility and responsibility to act within market rules on, individual autonomy and the ability to set self-determined goals appear to be limited to market participation. The market is seen as an inherently dynamic system developed over time. According to Hayek, individualism refers to social progress and conformity to society. The aim of this paper is to respectfully examine the apparent inconsistencies and limitations of how individual freedom and choice have been conceptualized by neoliberal thinkers, through an analysis of the works of Hayek and Friedman. Neoliberal policies articulate the notion of free will and question the definition of freedom from a purely economic perspective. By further examining these nuances, the study hopes to reflect on the personal and societal political implications associated with neoliberalism’s more limited understanding of self-government and voluntarism. Finally, an examination of balanced perspectives can add to the ongoing discussion on how best to organize social policies that maximize individual dignity and collective well-being in the long run at in a constructive manner.