Sigmund Freud was torn about civilization—indeed, he was one of “its discontents,” the term he used in Civilization and its Discontents. According to Lionel Trilling, Freud had a “quarrel with culture” and he sought to establish a place for the self to stand apart from culture. However, his primary emphasis was on the need to accommodate to culture. Consequently, the self’s adverse relation ship to culture has received insufficient attention within psychoanalysis. Moreover, Freud did not fully grasp our affinity with culture. The relationship between the self and culture, in my view, involves an ongoing negotiation between two deeply rooted longings: the wish to be a part of—and to stand apart from— culture. Creat ing a viable balance between these longings poses a major psychological challenge throughout life. I will explore the centrality and significance of the self’s struggle with culture and demonstrate, through clinical and biographical vignettes, that the ability to quarrel with culture and to value discontent-and make use of “adaptive apartness”-play a vital role in psychological development, emotional distress, and therapeutic change. Recognizing our dual relationship to culture also deepens our understanding of the history of psychoanalysis and its heretical dimension within our culture.