This paper poses the work of Gertrude Stein as a challenge to contemporary scholarship centered on theories of failure. Demonstrating that Stein’s notion of failure as a precondition for success derived from nineteenth-century selfhelp books, I follow her work with this paradox from her early writing about ethnic women, through her more recondite grammatical experiments, to her public emergence at the outset of the Depression. And I argue that Stein’s move from literary experiments rooted in the question of identity to her conservative rhetoric about white masculinity in the 1930s should serve as a warning to critics invested in failure as a figure of opposition.

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