This article takes the form of a discussion between Flora Parrott (an artist) and Harriet Hawkins (a geographer), who first brought together their existing interests in caves and the underground in 2015. Gully Cave (southwest England), a site of their shared “fieldwork,” and two experimental workshops offer the context to reflect on their evolving work together. This exchange, edited from a series of emails, reflects the evolving, looping form their collaboration has taken, circling around key themes including the importance of time, failure and trust in the process of development, and discussions around expertise and experimentation.