Bessie Head’s postcolonial writing represents multiple, shifting identities spanning a dual-belonging from diasporic migrant to refugee/national which can be traced back to the evolving socio-linguistic terrain of postcolonial Botswana. Writing in English, Head’s literary oeuvres write back to the Empire, focusing on these earlier concerns but, also advocating for a Pan-African globalised Africa, so as to harness a unified solidarity that combats the neo-colonial exploitation of the continent. In this, Head’s writing might be seen as pre-empting Selasi’s Afropolitanism which celebrates a global, cosmopolitan identity for Africa, claiming Africa as a seminal site in the world and providing a novel lens to critique Head’s postcolonial Anglophone legacy. Head challenges the lack of the African female subaltern’s voice in the post-colony, and in so doing, not only breaches this silence, but also argues for a more inclusive and robust representation of the intersectional experiences of African women. This chapter recognises the highly contested intellectual space that postcoloniality occupies and focuses on Head’s short stories to make three arguments. First, it analyses the postcolonial encounter between empire and colony through focus on the transforming socio-cultural environment, migration and its impact on women. Second, it examines how Head re-imagines new gender embodiments that disrupt traditional social discourse focusing on marginalized female voices that challenge the postcolonial English-speaking patriarchal culture to negotiate a novel, African female identity. Third, it focuses on a dialectical interaction between de-colonization, neo-colonisation and globalism to offer a nuanced understanding of the African woman in an evolving postcolonial socio-linguistic and cultural habitat dynamic.