This paper examines intertextuality between Virginia Woolf’s Orlando and Yann Martel’s Self, focusing on the way in which each text grapples with undoing gender essentialism. Despite being set in different times and spaces, both novels demonstrate common threads: the protagonist challenges binary gender norms and heteronormativity; their gender is unintentionally transformed. In this regard, Martel’s novel should be understood as a successor to Woolf’s Orlando, as it is advertised as “A Modern-Day Orlando” by the publisher. Strangely enough, however, both texts have rarely been examined together. Thus, I argue that Orlando and Self resonate with one another as they explore gender and sexual fluidity through their main characters while simultaneously problematizing fixed categories of sex, gender, and sexuality, along with language derived from binary and heterosexual assumptions. Woolf and Martel experiment and break down rigid distinctions of gender, language, and even literary genres by blending biographical or autobiographical forms with other literary styles in their respective novels. Gender nonconformity practiced by the two characters illustrates that gender is performativity and one’s self is constantly negotiated through interactions with others. Hence, this paper interrogates how Woolf and Martel envision gender non-conforming subjects’ livable lives to demonstrate the politics of queer life.