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Scholars have shown that professional expertise does not solely lie in an individual’s skillset or body of knowledge that one holds. Rather, expertise is also shaped by a myriad of contextual factors that enable professionals’ core skills and knowhow. While social scientists studying professionals have clearly established the contextual nature of expertise, it is unclear how professionals themselves may come to understand the broader social structure in which their expertise is embedded and how developing such awareness changes how they work. Through this study of global surgeons and anesthesiologists – doctors who work in high-income countries (e.g., Canada, United States, Europe) that do volunteer surgical work in low-income countries (e.g., various countries in Africa) – I aim to better understand this little-explored phenomenon. Drawing on interviews and observations, findings reveal that as these doctors moved back and forth between high and low-income countries, while their own competencies and the skills of their hands remained constant, their sense of expertise - how they gauged their ability to have an effect - did not feel the same. I unpack the various contextual factors in low-income countries that shifted these doctors’ sense of expertise. I find in experiencing these shifts, they experienced the contours of their expertise - the contextual factors that shaped their expertise became salient to them. Ultimately, such awareness changed how they viewed their expertise and they profoundly reconfigured their work. Overall, findings contribute to the professions literature by showing how professionals themselves may develop awareness of the contextual nature of their expertise and how doing so can deeply change how they work.