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In this chapter we propose harmonising career development with positive psychology by merging asset-based and career construction approaches. Basing our discussion on ongoing intervention research endeavours in South Africa, like others (Schreuder & Coetzee, 2006; Watson & Kuit, in press), we infer that individuals can be assessed and guided during career development in terms of existing personal and cultural contexts in order to attain fulfilment. Positioning our theoretical framework within segments of an asset-based approach, and career construction-post-modern-narrative approaches (Hartung, in press; Savickas, 2001, 2006), we propose possible value in engaging positive psychology issues in career development. Whereas the asset-based approach serves to recommend possible ways in which practitioners could ascertain and mobilise adolescents’ personal and contextual assets as capital in career development, incorporating a career construction-post-modern-narrative viewpoint provides us with unique ways in which to comprehend and counsel diverse adolescents.