This chapter investigates how the artists navigate multiple and at times conflicting identities within the challenges of working in unfamiliar transprofessional contexts. It also investigates the expanding professionalism of artists in the transprofessional realm of artistic interventions in organisations. Ariane Berthoin Antal argues that artists’ professional identities and also responsibilities are geared towards some fundamental values in the arts, and that it is vital for artists to maintain such values as they collaborate with other professions. To exemplify expanded work in transprofessional contexts, our attention now turns to the experiences of four artists—a theatre director, a performance artist, a dancer, and a dramaturg—who took part in the pilot programme at Uniarts. It is imperative in higher arts education to discuss critically the relationship between professionalism in more traditional artistic practice and the expanding professionalism of hybrid artists in new transprofessional domains.