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This paper explores the processes, strategies, and methods used when preparing an expressive vocal performance from the point-of-view of the artist. The study tracked the development and performance preparation of 13 university students studying classical voice performance or music education. Participants were asked to choose one unfamiliar piece from their repertoire and complete three surveys administered at the beginning, middle, and end of their study term. Each survey was geared toward the participants’ level of preparation and pertained to their approaches for learning new repertoire, the application of constructive criticism from peers and instructors, and experiences during and after their initial performance. Unlike studies focussed performance preparations of instrumentalists, this study focussed on singers, and take into account needs specific to singers, i.e. developing skills in emotional connection to text, character development, and emotional communication through body language and facial expression. The results support a three-phase model of skill acquisition marked by a period of introduction and deliberate practice, a middle associative phrase marked by drawing personal connections, and an autonomous phrase marked by performance readiness.