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Research has established that organizations benefit from being “optimally distinct,” i.e., both like and sufficiently different from competitors. We know less however about how producers think about and enact their strategic positioning choices. We explore these questions through a qualitative study of chef-owners who started their own restaurants after training with well-known mentors. We produce an inductive account of chefs’ strategic positioning choices as they relate to their former mentors, finding two types of strategic identities—legacy and divergent—which are shaped by occupational pressures and interpersonal mentoring relationships. This research generates insights into the microprocesses associated with optimal distinctiveness, i.e., the ways in which producers themselves think about navigating pressures involving similarity and difference and the constraints they face in their strategic choices.