Capitalism inheres alienation as a fundament of modern life, twisting the root of being such that a sense of pervasive estrangement becomes the condition undergirding much of our phenomenal existence. Alienation, I argue, formed in the cleavage of capital mediation, leaves us reinscribing its tenor across multiple spheres, as we are compelled to not only maximize capitalist growth, but also maintain the fullness of capitalism beyond the economic realm. To locate this argument, I begin with a brief description of Marx's analysis of capital as an alienating force. In the second section of the article, I employ Heidegger's existential analytic to argue that capitalist alienation is a perversion that shifts and informs how we exist, as we are called not only to accumulate but also to justify capitalism as a reifying force. I approach the analysis by looking at three phenomena: first, the issue of transcendental debt; second, the emergence of neoliberal idle talk as a supplement to capitalism; third, the oppression of the built environment, as capitalist efficiencies are prioritized in a globalizing world. Given the robustness of phenomenal encounters with capitalism, it is increasingly difficult to argue that education might offer solutions for issues of alienation. Nonetheless, this very prevalence is what makes the stakes of some kind of educational response clear. As such, I conclude the article with an exploration of what might be done to disrupt capitalist tendencies through a pedagogy of respite.