The speculative direction that Fink in the ’30s had imprinted on phenomenology finds its development – distant in many ways from its theoretical premises in Husserl’s thought – in the first university lectures of the post-war period, among which Vom Wesen der menschlichen Freiheit (1947) is of peculiar relevance. Some common threads connect Fink’s early phenomenological reflections with his following attempt to develop a philosophical cosmology and anthropology. In the course of lectures here examined we can see the revival of the theme that considers philosophy – understood as a radical inquiring, open to the world and at the same time to the self of the human being – the primary place of freedom. In connection with this theme Fink theorizes a concept of freedom that does not confine freedom to a subjective polar opposite to nature, but focuses on the exposure of the human being to the world. Fink, indeed, starts a discussion on the question of freedom through a comparison between two opposite patterns of thought, namely the philosophies of Kant and Nietzsche, read with a perspective that puts both these philosophies in contrast to the absolutization of subjectivity in the systems of German idealism.