Sharing experience through story-telling and storied-telling is a universal human practice that can be traced through history. From the epic narratives of the Mahabharata, Homer’s The Odyssey, Chaucer’s Canterbury Tales through to contemporary works, narratives have been employed to explain, entertain, instruct, mystify, and mentor. Jerome Bruner first proposed the concept of “narrative thought” in 1986 to challenge a singular focus on thought as reason (characterised as paradigmatic thinking). For Bruner, through narrative we tell stories that conjure possible alternative realities that allow us to explore the uncertainties, the unexpectedness, and the irregular in our worlds. This paper focuses on the concept of “mentoring conversations”; those conversations held between eminent artists and early career professional musicians who were enrolled in an industry-led longitudinal professional learning program. Mentoring is a relational act, founded in reciprocal, collaborative sharing of knowledge and experience with learning at its core. In such relationships in telling our life, our autobiography is always an “interpretive feat” (Bruner, 2004, p. 691) offering engagement points for participants. This paper aims to identify the life and learning lessons that emerge from such conversations. Data were generated through audio recordings of 13 artist conversations undertaken as group conversations between an eminent artist, program participants (2 early career musicians), and, program directors (2). A researcher was present at each conversation taking field notes in addition to sound recordings. Artist participants included eminent composers, writers, playwrights, choreographers, theatre directors, interdisciplinary and visual artists. Each participated in collaborative and socially engaged practices. Transcripts were analysed through thematic analysis (Braun & Clark, 2012) with emergent themes including: how to establish a viable enterprise as an artist (looking after yourself as an artist; running a business; asking for money), building a unique profile (finding your purpose; knowing your working process; building an audience; finding your people; building collaborations), and, the “usefulness of failure.” As a component of all conversations program participants described their projects, a process that provided opportunity to revisit ideas, leading to increasingly mature and detailed accounts of their practice. This process assisted their learning how to communicate as creative initiators with leading professionals. Implications for music education include providing learning experiences that support: the cultivation of healthy artistic practice across the dimensions of personal and social well-being; creative collaborative practice rather than the cultivation of soloistic career perspectives; and, the embrace of uncertainty and failure as learning opportunities.