This article explores a small sample of musicians in two European musical contexts – the Netherlands and the UK. It examines the relationship between the conditions of national music industries and the strategies used to negotiate a career in music and the extent to which musicians frame their careers as entrepreneurs. Interview data from two projects with early-career musicians form the basis of our secondary comparative analysis. We argue that their strategizing can be framed as a set of responses to their local structural conditions. However, neither set of responses produces market advantage. Instead, traditional power and economic relations that reinforce the logic of the hegemonic mainstream industry tend to prevail, whereby only a very small fraction of the aspiring musicians can sustain themselves financially in music.