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This article asks what it might mean to live resourcefully in the contemporary cultural moment, one characterized by multiple demands on our time and attention, an accelerated and overstimulating pace of life, and an increasing fragmentation of psychic and affective space. Bringing Winnicott into conversation with Lacan, the author argues that, despite their obvious differences, both psychoanalytic theorists view excessive psychic integration as an impediment to creativity. More specifically, the Winnicottian notion of the False Self is held to be conceptually quite similar to what Lacan means by an ego-bound self that is unable to overcome its narcissistic fantasies of coherence and wholeness. The article reveals that Winnicott and Lacan help us understand that creative living entails accepting existential insecurity as an intrinsic component of "the human condition." Yet it also highlights the limits of this perspective by acknowledging that there are instances where insecurity arises from oppressive sociocultural circumstances rather than from the "universal" complexities of human life. The aim, in short, is to demonstrate that existential instability and precariousness are the flipside of creativity, without at the same time turning these concepts into a fetish for postmodern subjectivity.