The modernist writer Gertrude Stein is well known for her innovative approach to literary prose. Far less known is the fact that Stein's career started in the emergent field of the brain sciences, first at Radcliffe College, then at the Johns Hopkins School of Medicine. In this contribution, I trace Stein's scientific trajectory and examine the reasons that compelled her to abandon a career in science, turning to literature instead. Stein's career as a scientist was initially very promising, and began to decline only in her last two years at Johns Hopkins. With her degree in jeopardy, she was offered one last chance: she would be allowed to graduate if she completed a last piece of assessment, consisting of a model of a young human brain. Alas, Stein's model was a disaster-and possibly a deliberate one. In the Autobiography of Alice B. Toklas, written over thirty years after the sour end of her scientific career, Stein attributed her failure to "being frankly openly bored" by medicine. In reconstructing the circumstances that culminated in Stein undermining her own performance by reimagining a "modernist" model of the brain, I show that Stein's rebranding of her failure as "boredom" was itself part of a broader act of disobedience toward the authority of neuroanatomy, whose status was far more uncertain than how its practitioners-Stein's own teachers-viewed it.