In this article, we introduce a narrative approach to biographical learning; that is, an approach that considers autobiographical storytelling as a practice through which claims about life history are performed and negotiated. Using insights from narrative theory, we highlight evaluations in those narratives and suggest their crucial role in promoting self-reflective thought. The research area is unemployment, more specifically, work transitions following company restructuring and redundancy supported by outplacement services. Recognizing the learning potential in autobiographical storytelling, the article examines job-loss narratives told by people made redundant. The analysis focuses on strategies used in moments of evaluation. Our findings point to a variety of rhetorical strategies, different kinds of reflexivity and, in turn, variation in the potential for biographical learning. (Contains 1 table.)