This article explores questions of audience and personhood in the diary of Akinpelu Obisesan, a Yoruba man who lived in colonial Nigeria. In particular, it examines how Obisesan wrote between the genres of autobiography and biography so as to generate a sphere for self-fashioning in the colonial context. After introducing Obisesan and exploring briefly the relationship between autobiography, diary writing and the self, I show how Obisesan’s diary narrated a deeply relational form of personhood, which he both generated as a writer and consumed as a reader. The article analyses this narrative, exploring how Obisesan constituted various real and imagined audiences for his diary, while simultaneously claiming his privacy and ‘archiving himself’ into a tin trunk. In the final section of the article, I present a close reading of sections of the 1927 diary, to show how, when writing his diary, Obisesan projected multiple audiences into his text. He used these audiences as a foil for enhancing his own sense of self, thus constituting his personhood and legitimating his precarious social position in colonial society.