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Psychoanalysis has, almost since its inception, regarded artistic creation as a privileged window to more universal psychological dynamics. If creative writing is interesting in itself, its failure can be fascinating. It is not unusual for some successful authors to find themselves unable to write. They suffer what is commonly known has “writer’s block,” a term coined by the psychoanalyst Edmund Bergler in his seminal study of blocked writers in the 1940s and 50s. This paper illustrates how the psychoanalytic study of “writer’s block” can go way beyond Bergler’s theorization. A writer who cannot write is also someone experiencing inner conflict, a self not living up to its expectations, a person that has lost the ability to play. Freudian, ego psychology, and object relations theory are some of the theoretical lenses used to look at “writer’s block,” and to show how this circumscribed phenomenon can shed light on more common struggles and muddles. A brief narration of the author’s experience of writer’s block is presented as an illustration of the parallels between psychoanalysis and writing, especially regarding the importance and use of reverie.