This article explores how universities might engage more effectively with the imperative to develop students’ twenty-first century skills for the information society, by examining learning challenges and professional learning strategies of successful digital media professionals. The findings of qualitative interviews with professionals from Australian games, online publishing, apps and software development companies reinforce an increasing body of literature that suggests that legacy university structures and pedagogical approaches are not conducive to learning for professional capability in the digital age. Study participants were ambivalent about the value of higher education to digital careers, in general preferring a range of situated online and face-to-face social learning strategies for professional currency. This article draws upon the learning preferences of the professionals in this study to present a model of twenty-first century learning, as linked with extant theory relating to informal, self-determined learning and communities of practice.