In my paper, I attempt to accomplish a twofold task: first, to argue that in order to understand important features of Deweyan work, a thorough analysis of the roles that uncertainty, courage and imagination play in Deweyan thought is required. Second, based on such an analysis, I try to show that such features are essential for education to happen. Moreover, courage, imagination and uncertainty taken together work to frame an understanding of education and learning as challenging and even risky enterprises. I develop my analysis against the current, 'official' picture of education promoted worldwide, one in which courage, imagination and uncertainty are exactly the features that come to be eclipsed by the neo-liberal educational agenda. Thus, I claim that education with its roots in imagination and courage is directed toward 'unattained possibilities' as its own, proper aim.