The present analysis of the evolution of the concept of freedom in Ernst Tugendhat’s philosophy aims to highlight several interesting facts. First, Tugendhat attempts to describe the meaning of Kant’s statement “I could have acted otherwise” from a non-transcendental perspective. Second, he makes an effort to avoid the classical Kantian dilemma of the relation of free will and determinism by posing the question differently. Third, he situates the issue of the relation of freedom and causality in the framework of the inner structure of freedom – examining it from the perspective of the human’s relation to him- or herself. Fourth, he attempts repeatedly to overcome the impossibility of considering freedom in the objective language of causality. The paper demonstrates why the issue of freedom remains a central problem of continental philosophy.