In this paper, we employ a comparative life course approach for Canada and Germany to unravel the relationships among general and vocational educational attainment and different life course activities, with a focus on labour market and income inequality by gender. Life course theory and related concepts of ‘time,’ ‘normative patterns,’ ‘order and disorder,’ and ‘discontinuities’ are used to inform the analyses. Data from the Paths on Life’s Way (Paths) project in British Columbia, Canada and the German Pathways from Late Childhood to Adulthood (LifE) which span 28 and 33 years, respectively, are employed to examine life trajectories from leaving school to around age 45. Sequence analysis and cluster analyses portray both within and between country differences – and in particular gender differences – in educational attainment, employment, and other activities across the life course which has an impact on ultimate labour market participation and income levels. ‘Normative’ life courses that follow a traditional order correspond with higher levels of full-time work and higher incomes; in Germany more so than Canada, these clusters are male dominated. Clusters characterised by ‘disordered’ and ‘discontinuous’ life courses in both countries are female dominated and associated with lower income levels.