This chapter is based on an interview Donna Lee Brien and Kiera Lindsey conducted with Ffion Murphy, who reflects on the life of Australian composer and music critic James Penberthy, AM, and her long involvement with both his story and that of his third wife Kira Bousloff, a former member of the famous Ballet Russes. Artist and organiser, mentor and collaborator, Penberthy’s contribution extends beyond his numerous and diverse compositions. He co-founded significant and enduring cultural organisations, including West Australian Ballet and West Australian Opera, and was a determined promoter of Australian music during decades when European artists and composers dominated Australian concert halls, theatres and airwaves, including the programs of the national Australian Broadcasting Corporation (known as the Australian Broadcasting Commission for much of Penberthy’s career). The prospective biographer would seek to render elements of Penberthy’s personal life alongside cultural transformations he witnessed, participated in and helped to create during several decades of the twentieth century. Coining the term ‘conceptual speculation’, the chapter speculates on avenues for exploration, and some challenges, including reservations about an outsider to the art form attempting a musician’s biography.