The will to have freedom and to experience equality in learning form a vital relation to our capacity to make choices in life. This article offers a comparison between Sartre and Rancière that is new to the field of research in education and contributes an argument for a relational philosophy of freedom and equality. Existentialist insights into how we experience the world through affect and embodied intelligence are raised in this exploration of the contemporary significance of 'freedom' in education. Questions of capacity for free choice are addressed, in discussion of historically different opportunities across identifications of gender, class and ethnicity in education. In this comparative approach, constructive parallels are identified between Sartre's philosophy of freedom and Rancière's method of equality, that form a new relation to the arts and learning. I argue that there are positive connections that can affirm flexible, responsive and representative free thinking in creative practice.