Having considered the destabilising questions of what musical work is, what it means, and the nature of ‘success’, this chapter examines the ways in which musicians seek answers to those questions. Navigating this landscape, musicians turn to other forms of reference. This the authors term: ‘The Status of Value’. This evaluation takes place in two key ways: firstly, online, and secondly in the reified and ill-defined music industries. Firstly, the chapter looks at how musicians’ relationship to technology – in the form of the online sharing and the consumption of their work – creates an environment of perpetual anxiety. This takes place as the emotional vulnerability inherent in receiving feedback for creative work intersects with an injunction to participate in an exhausting quest to maintain relevancy. Subsequently the authors examine how musicians engage with processes of value measurement offline, within the music industry itself. Ideas of luck, randomness and timing are understood as playing a key role in the careers of musicians, and these ‘unknowns’ produce high levels of emotional distress and anxiety. The chapter concludes by exploring one of the most profound anxiety-producing tensions in professional musicians’ lives, where the precarious and unpredictable workplace comes up against entrepreneurial ideals of control. The authors conclude that contemporary notions of artistic empowerment in the digital age are dangerous, as they reinforce an idea of individualised entrepreneurial control which is largely illusory.