Emerging from the Paris surrealist group, the English-born writer and painter Leonora Carrington (England, 1917—Mexico, 2011) was perpetually suspicious of orthodoxy. She often pokes fun at, parodies, and ultimately upsets traditional hierarchies of power. In her work animals impart wisdom, Goddesses loom large, and domestic spaces become sites of occult power. In this article, I investigate Carrington’s suspicion of gurus with claims to esoteric truth. Carrington participated in Fourth Way groups run by students of G. I. Gurdjieff (Christopher Fremantle) and P. D. Ouspensky (Rodney Collin). However, while she had a deep interest in the teachings, Carrington remained suspicious of the group practices of the Fourth Way, as can be seen in Elena Poniatowska’s fictionalized biography Leonora (2015). This article explores Carrington’s contact with the ‘Work’ in order to shed light on the character of Dr. Gambit in her 1950 novel, The Hearing Trumpet, commonly thought to be a parody of Gurdjieff. In doing so, it will investigate Carrington’s feminist objections to the role of the guru, while also contributing to a discussion of the unease some felt toward the praxis of the Fourth Way, despite their attraction to the philosophy.