This chapter discusses the contrasting philosophies of Catharine Macaulay and Edmund Burke regarding the fundamental nature of political society and the approaches to take on reform. Macaulay’s philosophy revolves around the core ideal of freedom as independence from arbitrary control. Additionally, Macaulay’s work recognized that people’s beliefs are shaped by the social environment but could be manipulated by elites. On the other hand, Burke’s philosophical beliefs are organic, contextual, and pragmatic while addressing the complexity and range of social considerations and human motivations that contribute to a viable and productive state. However, Burke’s philosophy could be challenged as to whether he provides protection against possible abuse of power or not. The chapter also covers the weakness in their philosophical works while considering equal citizenship rights for women and minority social groups.