This chapter examines why privileging calculative or technical thinking is particularly problematic in medical practice. Because medicine and medical education focus on the “real” and the “scientific” (assessing and treating biological disease), the lived experience of illness—including existential issues such as suffering, fear, and inescapable uncertainty—are left largely unaddressed. Thus, some clinicians, especially those who view themselves as scientists or technicians, may believe that they are not called to attend to these issues. It is not enough, however, to say that doctors turn away from answering this call to care simply because they have been trained within a medical culture that fails to acknowledge the lived experiences of patients that fall outside the bounds of calculative thinking and technical rationality. Turning away from the reality of vulnerability and finitude is part of the shared condition of being human. Through an exploration of the philosophical work of Kierkegaard, Heidegger, Merleau-Ponty, and Nietzsche, this chapter shows that medicine’s preoccupation with science, detachment, and certainty is a manifestation of the basic human desire to turn away from the anxiety that emerges in the face of human suffering and the struggle to make meaning in the face of profound illness and death.