This article shows that the concept of choice is central to Isaiah Berlin’s liberalism. It argues that his valuing of choice is anchored in a particular conception of human nature, one that assumes and presupposes free will. Berlin’s works sketch a metaphysics of choice, and his reluctance to situate himself openly in the debate on free will is unconvincing. By introducing the theory of autopoiesis, this article further suggests that there is a way to take Berlin’s value pluralism seriously, by considering sets of values as autopoietic conscious systems. Drawing on the works of Maturana and Varela in biology and Luhmann in sociology, autopoiesis strengthens value pluralism and acts as a critique of liberalism. By putting objectivity in parenthesis, autopoiesis finally allows for value systems to coexist side by side in a stronger sense than Berlin’s liberalism ever could.