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In this paper, the author engages with the work of Marion Milner, specifically her book “On Not Being Able to Paint,” which is mined for its insights into creativity and its inhibition through the lens of mid-century Independent Group psychoanalysis. Through a close reading of Milner’s theories about the nature of self-immersive states the deep anxieties such states can stir, the author elucidates Milner’s approach to the psychodynamics of creative blocks. From there, the author provides an in-depth case example of a patient who is suffering from extreme writer’s block. The clinical material is explored through the Milnerian lens, which is then expanded to include the insights of other object relational and relational thinkers which add dimensionality and nuance to Milner’s original insights about creativity. In the final portion of the paper, the author turns the focus to an exploration of the underlying philosophical assumptions about the relationship between the individual and the culture that are implicit within Milner’s work and within any psychoanalytic theory. The author highlights the contrast between a midcentury object relational vision in which an enriched sense of individuality is valued and seen as socially productive, and the contemporary critique of individualism leveraged through the “political turn” of contemporary psychoanalysis, particularly form within the American relational school.