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The analogy of ‘stepping stones’ through education and employment is a powerful organising idea that evokes a sense of staged and linear progression through education to employment across the life course. For Indigenous people, transitions from school to university, or from a low-paying job to a higher paying job, are troubled by the complexities of racism, classism and geography, in addition to the effects of deregulated labour markets and economic dislocation that impacts both current and future generations. Transitions between schooling and work, the stepping stones to success, do not appear to function in the same way for Indigenous people as they do for others. This precarity is an effect of schooling experiences and changes to the nature of work, but I argue is largely due to the absence of Indigenous self-determined stepping stones. What it means to live a good Indigenous life is often informed by our accountability to the past as much as it is our hopes for the future. Non-linear patterns in schooling and work reflect the absence of Indigenous authority in compulsory systems; building stepping stones to Indigenous futures that hold both purpose and responsibility are critical to addressing this precarity.