This paper sets out to ask how cultural workers on Scottish islands come to narrate their work and everyday life experiences. We ask this question in the context of two dominant doctrines that can influence whether or not these experiences are “good or bad.” The first doctrine describes attitudes toward creativity with reference to current discussions around cultural work and the idea of “creative.” The second doctrine highlights conceptions of islands as unique places with pastoral characteristics that need to be fostered and promoted. It is our contention that island cultural workers must continuously negotiate with these two frameworks in order to successfully achieve good work. If the negotiation is fraught with difficulties, the cultural worker will ultimately leave either this form of work or the island. For the purpose of this paper we focus on the narratives of two cultural workers located on two different Scottish islands to highlight the ways their particular narratives engage with the doctrines of creativity and islandness.