This study addresses the role of reputation in the career building strategy of early-career musicians in a transforming music industry. Drawing from interviews with 21 musicians, we find that musicians continue to believe that building their reputations within the established music industry is important for career success, despite technological changes that could lead them to focus instead on alternative career strategies. Our analysis proceeds in two stages that broadly reveal how market culture shapes workers' strategies. First, we discuss how musicians put considerable effort towards achieving particular career milestones that they believe will signal success to industry intermediaries. Second, we show that new technologies that connect artists directly to audiences without the need for intermediaries have allowed musicians to pursue new career building strategies. However, they have not eliminated musicians' belief in appealing to industry insiders through milestones. Even though achieving industry milestones may not lead to immediate economic benefits, musicians pursue them because (1) they believe that backing from industry intermediaries may result in later success and (2) they value the symbolic appeal and romance of being part of the industry.