Human beings have the extraordinary ability to talk with one another. They listen, talk, paraphrase, sympathise, and argue. Some people are better at performing these uniquely human behaviours than others. Some are born better at it, whereas others improve with practice and training. Many people benefit from the support of an educator or counsellor to learn how to understand exactly what they want or need to say and to then put it into words. What is truly remarkable about this human ability is that it not only occurs in real conversations spoken aloud amongst individuals, but that it also occurs inaudibly as imagined conversations in the mind. This chapter describes the theoretical foundation and practical implementation of My Career Chapter (McIlveen, 2006), a narrative career assessment and counselling tool designed to enable expression of the client’s dialogical self and the subsequent articulation of a career autobiography. In doing so, the chapter also describes how the theory of dialogical self can be applied to practice in the form of a career writing (Lengelle & Meijers, 2014; Lengelle et al., 2016) intervention for narrative career counselling and career development learning.