This article celebrates friendship as a valid starting point for scholarly enquiry and uses conversation as a valuable methodology. While completing their doctoral research on modernist short stories and women’s art collectives, co-authors Rydstrand and Mayhew discovered New Zealand author Katherine Mansfield was a contact point between their respective projects. Around 1981, Harridan Screenprinters quoted Mansfield’s injunction to ‘Risk anything’ on a poster, invoking Mansfield as a role model—as a leading modernist author and as a risk-taker. Mayhew later gave Rydstrand a copy of the poster as a thesis submission gift. This article explores interrelations between personal, creative and professional risks, from Mansfield’s avant-garde milieu of the early twentieth century, to the dynamic scene of second-wave feminism in Australia, and finally to the precarious world of the twenty-first century academy, all brought together by the physical artefact of the Mansfield poster. In this threefold engagement, we counter the presumed masculinity of experiment and champion feminine forms of risk.