In order to make sense of people’s experiences and the stories they tell, we need a theorisation of the subject. This needs to account for both the psychic and the social dimensions of our being, as well as offer scope for thinking about how these two dimensions are entangled and interact in complex and complicated ways to simultaneously constitute and alienate us as subjects. In this chapter, I explore the complex conceptual terrain and complicated history of alienation, including its mutual implication of self and other, and its entanglements with thought and emotion. I go on to consider how the organisation of education and schooling today work to inhibit us from recognising and creating the sort of vibrant correspondences between individuals, and between them and the world. I explore how this force discourages us from recognising the regenerative capacities of solitude that are essential to personal and collective thriving, instead leaving us with a frustrated feeling of being clamped in our own private traps and alienated from ourselves, our work, our worlds and each other.