In Hannah Arendt’s work, the crisis of the education in the twentieth century reflects the collapse of the political and the questioning of its central categories: world and natality. This study links her position regarding education with the political phenomenology scattered throughout the rest of her work. The discussion is developed through a critical analysis of the work of Arendt, with a specific focus on the texts she wrote in her youth, and her link to Heidegger’s thought. Perplexities of the totalitarian phenomenon and its connection with modern changes are the main topic. It is concluded that our modern political crisis turns into a crisis of sense, because it nullifies the world and the human ability to build it: freedom.