Kierkegaard’s concept of leveling is applied to the dynamics of envy, particularly as they come into play among psychoanalysts doing clinical analytic work. This is illustrated in two clinical vignettes. The technocultural surround of the digital age impinges on analytic identity in ways that can evoke fantasied retreats into sameness and erasure of distinction. The “digital reality principle” is introduced as a way of conceptualizing an aspect of the hatred of thinking and certain envious responses to distinction. Charisma is considered as a possible release from sameness and the prevalent homogenization of experience. Among analysts, an internalized leveling process can sometimes function as a bulwark of homogenization.