Migrants, along with youth, stand at the forefront of gig economy in many countries. Gig work intersects with other domains of migrants’ post-migration life, including career development. To substantiate “plural systems of knowledges” [Sultana, R. G. (2021). For a postcolonial turn in career guidance: The dialectic between universalisms and localisms. British Journal of Guidance & Counselling, p. 5] required for understanding such intersecting boundaries, qualitative research that prioritises migrants’ local knowledges is essential. This research systemically explores the career development of New Zealand immigrants working as rideshare drivers in Australia and considers the impact of gig work on their career development through the lens of the Systems Theory Framework (STF) of career development. Using a qualitative exploratory multiple case study design, interviews were conducted with four rideshare drivers. Findings highlight the role of systemic influences in the intersections of migration with gig work and career development. The role of the STF of career development in facilitating a systemic exploration through both stages of data collection and data analysis is highlighted.