Well-developed career stories are becoming increasingly important for individuals as they navigate an unstable and unpredictable labour market. Existing narrative approaches in career guidance do not yet clearly identify the learning process by which career stories are created. In this article, a model of transformation-through-writing will be introduced to help explain the learning process that occurs when narratives are used for constructing career stories. We propose that this learning process occurs stepwise in four cognitive stages: sensing, sifting, focusing, and understanding. To progress through these stages, an internal (with oneself) as well as an external (with relevant others) dialogue is needed. The case study used to illustrate the process is a story of unemployment and effectively shows how narratives can be created through expressive and reflective writing and how such a process may foster career learning in response to a boundary experience. (Contains 1 figure.)