The article confronts key notions framing our understanding of modernity, such as rationality, knowledge, freedom and democracy, opening the space of a critical interpretation undermining the superficial take on modernity as an embodiment of integrity, putting together the noble principles of knowledge and liberty. Drawing on the thought of Max Weber, exploring the symbolism of his metaphor of “iron cage of rationality”, the article emphasizes a paradoxical sense of the experience of modernity. In concluding statements it defies and calls into question a standard reading of democracy, viewed as an embodiment of freedom and rational self-definition.