French philosopher Gilles Deleuze often expresses his belief in the power of experimentation in writing and praises Anglo-American literature for its venture into experimenting with lives. According to him, reading a long list of Anglo-American writers, including Henry James and F. Scott Fitzgerald, shows us that the sense of a life cannot be grasped, as it is full of unknown materials and their obscure, immaterial effects. Deleuze argues that healthy writers, having faced the impossibility of encompassing the entirety of a life, create lines of flight, move along with them, and discover worlds that enable themselves to transform. Then writing, as a process of becoming, turns out to be impersonal, while cracks and ruptures, often considered failures in life, appear as opportunities for literary creativity. This article will first explain why Deleuze views Fitzgerald’s The Crack-Up as a literary experiment with a life by focusing on his views on the impersonality of writing. Then drawing attention to Fitzgerald’s reference to American critic Edmund Wilson as his intellectual conscience, the article will attempt a speculative experiment with Wilson’s comments on James’s “The Turn of the Screw.” It will argue that Wilson’s sense of the text’s ambiguity, which is discussed by Shoshana Felman in depth, might have evolved critical interpretation into experimentation in a Deleuzian manner. Thus, the main protagonist of James’s novella, i.e., the governess, might have been considered as experimenting with a life as Fitzgerald does in The Crack-Up.