Bessie Head’s decision to leave South Africa for Botswana in 1964 at age twenty-six has been read as the consequence of apartheid’s oppressive racial politics that saw her racial ambiguity as particularly threatening. However, as her early South African work would suggest, Head, who would become Botswana’s best-known writer, was ostracized as much by burgeoning black nationalist discourses as by apartheid’s racism. This article argues that the existing anti-apartheid discourse in post-Sharpeville South Africa was inadequate in comprehending Head’s identity as mixed-raced and as a woman, as evident in her juvenilia. In this early work, Head undertook the double task of dismantling not only the racist discourse of apartheid but also the racist/masculinist elements of the available anti-apartheid discourse of her time, in an attempt to accommodate her dissident identity as an anti-apartheid writer and activist—but not male; and not black and not white. Gender, alongside her race, is seen to play a crucial role in Head’s inability to construct an anti-apartheid identity in an atmosphere of a sharpening racial dialectic.