Surgeons are often portrayed as mere technicians. Other skilled manual laborers, like mechanics, plumbers, and carpenters, face similar judgments that their work involves “doing” and not “thinking.” However, both surgeons and mechanics engage in deep thinking and deliberation related to their craft that is tied to action. Matthew Crawford—a philosopher and motorcycle mechanic—explores the nature of mechanical work in his book, Shop Class as Soulcraft: An Inquiry into the Value of Work, in which he proposes it is technical, intellectual, and moral in nature. Crawford’s analysis is pertinent to truly understanding the art of surgery. In this chapter, we draw on Crawford’s work to situate the surgeon’s work within the larger philosophical discussion on the value and nature of work. We discuss the epistemology of surgery, which arises from both doing and thinking, experience with the craft, and training under virtuous experts. Surgeons and motorcycle mechanics alike rely on tacit knowledge, practical wisdom (phronesis), and an understanding that failure is inevitable. Surgery and motorcycle repair are examples of the stochastic arts that require a particular moral disposition—especially honesty and humility. Finally, we discuss the implications of this work for the training and formation of future surgeons. The education of good surgeons requires time for deliberate practice and habituation, learning from virtuous exemplars, and participation in a thick moral community.