The goal of the current study was to explore the early antecedents of three facets of work life quality: job satisfaction, income satisfaction, and leadership emergence. Using Statistics Canada’s Youth in Transition Survey (YITS), the role of early leadership experiences, nurturing parenting, and parental work experiences on quality of work life was examined in two samples of Canadian youth followed between the ages of 15-25: (1) youth whose highest level of education was high-school or below, and (2) youth who pursued education at the post-secondary level. Overall, results supported the notion that early experiences and educational pathways play a role in shaping work life quality across the lifespan. While exposure to leadership in adolescence was associated with a young adult’s later emergence into leadership roles, nurturing parenting and social support held distinct implications for a young person’s entry to the world of work. Results have implications for research and practice.