Higher education students provide many reasons for their taking a particular degree. These typically relate to their current vocational interests and future employment prospects. This is significant since students’ vocational identities and consequent decisions develop in a complex dynamic of vocational personality, characteristic adaptations, and life stories, all interacting with affordances in the social, economic, and cultural contexts of students’ lives. Using contemporary personality theory and vocational psychology theory, we focus on the third dynamism - life stories - to explicate a method that facilitates assessment for and of learning in the context of career. Here we describe the conceptual and methodological dimensions of “My Career Chapter: A Dialogical Autobiography” (McIlveen, 2006) as an exemplar of an innovative pedagogical method with its conceptual foundations in vocational psychology and the theory of dialogical self. We will describe examples of its application in postgraduate studies and elaborate on its teaching and assessment affordances for career education. Finally, we will outline practical implications for the continuing application and evaluation of My Career Chapter, and the curricular vision that drives it, in higher education and career development learning.