This essay presents somaesthetics of discomfort as an extension of the field of somaesthetics as developed by Shusterman. Using the work of Peirce and Dewey as a foundation upon which Shusterman and Johnson have considered the body as the basis of aesthetics, I propose that somaesthetics of discomfort provides a means of enhancing bodily awareness and reflection useful for domains of inquiry, such as healthcare and design. Taking Peirce’s notion of the irritation of doubt in a literal sense, I explore bodily discomfort as the inception of inquiry. I consider work done by phenomenologists concerning experiences of comfort and discomfort, which includes definitions of each. My argument follows the perspective put forth by Peirce, Dewey, and contemporary pragmatists that experience is qualitative and that feeling is at the root of reflection. I explain how discomfort may be considered a type of aesthetic experience and provide examples of bodily discomfort as somaesthetic. In closing, I consider somaesthetic focus on discomfort as fostering moral imagination and empathy.