The concept of lifelong learning and the ways in which this learning takes place are of key importance for both students and professional musicians. Musicians in the 21st century need a broad and rapidly adaptable set of skills with which to build and sustain their careers, as substantial research shows that most musicians work within multiple roles that change according to their personal and professional needs. In order to forge new opportunities, musicians are often required to look beyond their initial training and experience to transition to new instruments and genres. There is limited research about the transition processes involved for mid-career musicians, especially in relation to how they train for cross-genre playing and the psychological challenges that they might face along the way, due to a lack of self-confidence or a poor sense of self-efficacy. This research project explored how continued learning and development took place for one professional musician, how alternate and additional musical skills were acquired, and what varied learning processes were involved. Using an autoethnographic approach, this research included a detailed examination and analysis of my personal transition from my formal training as a classical violinist to my current work as a professional vocalist and violinist across multiple other genres. The creative output during my Master’s candidature comprised two live performances, one video-recorded performance and a recorded album.1 Because this research commenced in 2016 and continued until mid-2021, this dissertation presents a substantial chronological exploration of my formal and informal learning processes, the inherent challenges I faced in crossing musical genres and in learning how to use a new instrument (my voice), and my musical development during this time. Data were collected through a range of techniques, including audio and video recordings and reflective journal entries. Conceptually, the study was based on the Learning by Design framework developed by Kalantzis et al. (2005) and explored different types of learning and a range of concepts related to belonging. The latter included self-efficacy (Bandura, 1977), Broadwell’s (1969) four stages of competence,Csikszentmihályi’s (1975) flow theory, imposter syndrome, (Clance & O’Toole, 1987), performance and contextual anxiety, and avoidance due to fear of failure (Papageorgi et al., 2007). I found that learning was a complex and multifaceted process, involving Kalantzis et al.’s (2005) four types of formal and informal learning processes working together: conceptualising, experiencing, analysing and applying. As I learnt more about my new instrument (voice) and new music genres, I started to feel a sense of belonging, with perceived higher self-efficacy, less self-doubt and diminishing feelings of being an imposter. My findings enabled me to construct a transition framework, based on my experiences. My research highlights the need for further investigation into identifying how transitions and lifelong learning could take place for other professional musicians, especially those who are mid-career. In today’s COVID-19 world, it has become even more important for musicians to consider transitions and lifelong learning.