Shaftesbury declared: “What I count True Learning … is to know our selves”. This study examines the strategies of argumentation expounded in Soliloquy, the essay in Characteristicks focused on self-knowledge. Shaftesbury experimented with several frames of reference because he was sceptical about the available templates for understanding human nature. His tentative stance betrays an epistemological predicament akin to observational science. This study will further explore the connection between the author’s non-magisterial style, the codification of a culture of urban conviviality, and the way in which scientific inquiry was enabled by being encoded as gentlemanly behaviour within a culture of honour.