Career preparation has gained increasing prominence in higher music education as governments and students alike demand a stronger focus on workplace readiness. While the existing graduate metrics work well for professions which feature traditional, full-time jobs, the potential for such a linear career path is limited for graduate musicians by fierce competition for work and a labor market in which precarious work is the norm. Music graduates tend to experience a career-long portfolio of part-time, casual, and contract-based work within and outside the music industry. This article reports on an innovative internship program that engaged student musicians in an in-curricular intervention related to their career thinking. The program and its assessments purposefully placed students into authentic learning contexts where their musical skills and their understanding of being a professional were challenged and expanded. Using the examples of scaffolded assessment tasks including an ePortfolio and a presentation of on-the-job learning, the article highlights students' reflections on how the internship engaged their career thinking and how the ePortfolio process helped them to curate that thinking. Students reported that the combination of an ePortfolio and scaffolded career thinking assessments enabled them to realize the relevance of their learning tasks and to create clearer career connections. Implications for the use of ePortfolios within WIL (work integrated learning) are discussed.