The launch of Saudi Vision 2030 in April 2016 prioritized job creation (and associated Saudization) to reduce unemployment amongst the Kingdom’s predominantly youthful population. Yet, despite moderate growth in employment in some sectors like mining and petrochemicals in certain regions outside the main cities such as the Northern Borders and Jizan, unemployment remains high and nearly 40% of Saudis in their early 20s are unemployed (Saudi General Authority on Statistics 2020). Existing research on young Saudis’ attitude to work points to disengagement, low motivation, and a sense of ‘entitlement’(Ramady, M.). Through employing a mixed method approach, this paper focuses on work narratives of Saudis from different regions to better understand the diverse attitudes toward work across the country. Nine in-depth interviews with Saudis who began working in the 1960s illuminate the way attitudes and aspirations have evolved, illuminating historical sociocultural factors that explain in part why resistance to state-led job creation initiatives to in the increasingly diversifying economy have not led to widespread labour market nationalisation success. The interviews are complimented by survey data from 700 young Saudis highlighting contemporary attitudes toward work and employment. These allow for an exploration of how regional variations in attitudes toward work have evolved over time, and whether these are mirrored in contemporary regional constituencies as well as those regional groupings residing in main urban centers. Drawing on the literature of sociology of work, narrative analysis uncovers the effects of rapid urbanisation on work attitudes. The narratives highlight the effects of replacing informal work with widespread public employment in the 1960s and 1970s on definitions of ‘good’ and ‘bad’ jobs (Kalleberg, A.; Jerome and Schmitt; Hodgkiss, P.). In addition to mapping Saudi work-identity narratives, the interviews capture insights from a generation of Saudis who experienced transformative economic and social developments over the past 55 years, allowing us to illustrate how historical events and economic shifts were perceived at different points in history. While studies on labor markets within the region are predominantly quantitative and economic, this study relies on the rich data narratives to highlight the source of attitudes and aspirations, potentially illuminating sociocultural factors that are often overlooked and could inform more effective policy interventions.