In this article the researcher reports on a longitudinal study which investigated the imagined identities of a preservice English teacher in New Zealand and compared these with the identities she negotiated in her teacher education and then teaching practice nearly nine years later. The teacher, an immigrant from the Pacific Island of Tonga, imagined herself working amongst members of her immigrant community but ended up teaching English at a privileged high school. The researcher used a short story analytical approach to analyze her narratives. Short stories are excerpts of data extracted from a larger set of data such as conversations, interviews, written narratives, and multimodal digital stories. In this case, short stories from a series of interviews were analyzed for both their content and the varying scales of context in which the short stories were constructed and interpreted. The analysis is informed theoretically by recent developments of the concept of investment (Darvin & Norton, 2015). The researcher includes reflexive personal commentary on his own positioning throughout the article, which concludes with suggestions for the use of short story analysis in teacher reflection and research.