Australia’s racial-colonial narrative has long depicted Indigenous Australian workers as lazy, deceitful, incapable, and unproductive or unwilling to work. Such racist stereotypes about Indigenous peoples still flourish today and in ways that often exclude us from discussions about worklife and lifelong learning and education. This leads to governmental and workplace policies and practices being formulated without accounting for the needs, aspirations, and cultural inclusiveness of Indigenous peoples. These exclusive practices therefore result in reinforcing pre-existing and problematic racist stereotypes about Indigenous Australian peoples and work. Against such a backdrop, this chapter draws on worklife history narratives from Indigenous workers to examine their contemporary experiences of worklife and associated learning. Detailed accounts of their experiences expose the diversity of work performed and learning undertaken by Indigenous workers across their lifespans. This analysis engaged an Indigenist Research Methodology (Rigney LI. Wicazo Sa Review, 14:109–121, 1999). Indigenist research is that led by Indigenous Australian researchers whose informants are primarily Indigenous Australian peoples. The research combines worklife history narrative interview method outlined by Salling-Olesen (A pyscho-societal approach to life histories. In: Goodson I, Antikainen A, Sikes P, Andrews M (eds) The Routledge international handbook on narrative and life history. Routledge, London, 2016) that is introduced and employed in this volume, and the Indigenous research method of Yarning as detailed by Bessarab and Ng’andu (Int J Crit Indig Stud 3(1):37–50, 2010). Data were analysed and themes identified through thematical analysis (Braun & Clarke. Qualitative Research in Psychology, 3(2):77–101, 2006). The accounts from Indigenous Australian workers draw attention to their exercise of agency, resourcefulness, determination, adaptability to locate new forms of work and to sustain employment and secure advancement. This chapter proposes that the Indigenous Australian workers informing this project actively resist unemployment and counter the colonial narrative about Indigenous Australian peoples and work. Instances of career mobility; and lifelong education supporting their ability to pursue careers and achieve first in family goals are evident. In all, this chapter provides the foundations for a reimagining of what the workplace could look like for Indigenous Australian workers when long-held stereotypes are confronted and transformative practices, such as authentic mentoring, are structurally embedded, embraced and promoted.