This chapter proposes that dialogical self theory (DST) offers a helpful view as it accepts the multidimensionality and multivoiced nature of individuals, who, in order to achieve a successful career, must be able to construct a flexible and workable narrative and do so as a result of an engaged dialogue where I-, meta- and promoter positions feature prominently. Career stories tell how the self of yesterday became the self of today and will become the self of tomorrow. Compared with more cognitive approaches, the DST stresses that an individual is much more capable of acting adequately towards his or her career, once he or she recognizes and acknowledges the existing complexities without resorting to rationalizing or finding simplistic explanations. The chapter illustrates the potential to study the developing self in career learning based on training conversations and provides some background information on the evolution of training conversations.