In 2007, the author embarked on a biography of Princeton mathematician John Horton Conway. She soon learned that her subject would test her creative mettle as a writer and artist. The charming anarchist that he is, Conway would push the boundaries of literary convention and the art of writing biography. A talented storyteller himself, he required an experimental approach in the telling of his life story. What resulted was a “meta-biography,” wherein the narrative is passed back and forth between subject and biographer, in order to accurately capture the artful nature of Conway's ingenuity, both in terms of his personality and his own creative works. Herein, as an adapted sampling, the author recounts her process, as well as what resulted in describing some of Conway's more eccentrically crafted contraptions, mathematical, whimsical, comical, and otherwise.