Identity work is widely regarded as a process through which people strive to establish, maintain or restore a coherent and consistent sense of self. In the face of potential disruptions of, or threats to, their identities, people seek to salvage their sense of self by resolving tensions and restoring consistency. In contrast to the current identity work literature, this research indicates that identity work is not always about seeking resolution and moving on, but sometimes about continuing struggles which do not achieve a secure sense of self. This paper seeks to elaborate the understanding of unresolved identity work by exploring three contexts of the everyday practice of indie musicians. An analysis of how they struggle to construct acceptable versions of their selves as songwriter, bandleader and front(wo)man allows us to develop the conceptualization of self-questioning (as opposed to self-affirmative, resolution-oriented) identity work.