In this paper, I analyse the Deweyan account of thinking and subject and discuss the educational consequences that follow from such an account. I argue that despite the grouping of thinking and reflective thought that has largely appeared in the interpretation of Deweyan work, Dewey discloses an inescapable uncertainty at the core of human thinking. This move is even more challenging given Dewey's firm faith in the power of intelligent action, and in education as the means by which human beings grow and create meaningful existence. I argue that throughout his work, Dewey dismantled the understanding of the subject as a detached and self‐assured centre of agency. In Deweyan understanding, on one hand, the subject is empowered to reflect on experience and to use this reflection to evolve new ways of acting, thus pushing experience forward. On the other hand, by acting, the subject can create new points of interaction within experience. This understanding of thinking and subject has far‐reaching consequences for education, which must be conceived not so much as the attempt to master and control experience but as the means to create new, unpredictable experience by putting new points of interactions into our relationship with the environment, changing our being‐embedded‐in‐the‐world. Dewey repositions educational, intentional agency away from control and mastery and in the direction of growth and openness.