In the following work, I intend to illuminate the importance of the lives and the works of Václav Havel and Aleksandr Solzhenitsyn. I have chosen to employ a multi-disciplinary approach - one that will include elements of political philosophy, educational theory, cultural theory, and literary criticism. I will analyze and compare their works, the convergence and divergence of their views, their shared emphasis on the theme of the 'ideological lie', and the lack of an alternative view in Post-Communist societies. I will demonstrate that their philosophical framework is not fundamentally or properly understood by the archaic dialectic between capitalism and communism that has shaped academic discourse for the last two centuries. For that reason, their works and central themes are still relevant; indeed the conceptual framework they have constructed can help illuminate the continued struggles faced by 21st century global society.