In this chapter, I engage with the OECD’s educational framework using a specific foothold, namely, the Deweyan theory of imagination and understanding of the role courage plays in educational practices. It is my argument that imagination and courage are inestimable educational features, and the eclipse of them, is, at the very same time, the eclipse of education as openness, meaning-creation, and projection into the future. However, such an idea of education seems to be far removed from the picture of education and learning which OECD enhances. For learning regime to work, in fact, imagination and courage must be tamed and, in a sense, erased from educational processes (see Chapters 3 and 4). This is true for the learning regime pursued by OECD presents a smooth, predefined vision of learning, one in which students must acquire predetermined skills, and traveling through already-defined learning tracks.