The effects of a global financial crisis, technological advances, political instabilities and ongoing environmental issues are impacting young adults’ transitions from secondary school education to work. This chapter interrogates recent case study research findings in this area through Amartya Sen’s (1992, 1999) capability approach, in which educators are challenged to provide culturally respectful school to work transitions for young Indigenous adults. It exposes some elusive practicalities of the conceptual foundations of the capability approach with its emphasis on individual well-being; while seeking systems-level responses to making cultural diversity strengthen, rather than diminish, transitions from school to working life. Transitions research has identified that geographical location, gender, socio-economic status, cultural and linguistic backgrounds are among a range of factors that impact on the nature of school to work transitions (UNESCO 2001 & 2009). Engaging transitions within the broader frameworks of institutions and systems provides a way of examining large-scale innovations through culturally diverse work-life trajectories (OECD 2000; Sweet 2009 & 2010). Accordingly, both conceptual and contextual engagement with the “wider disparities in the distribution of power, wealth and opportunity” that reflect policy-driven “unfair distribution of life changes” (UNESCO 2009: 6) is timely. This view is first explored conceptually through an analysis of the challenges and opportunities offered through taking a capability approach (Nussbaum 2003 & 2011; Sen 1992, 1993 & 2006) to investigating the ways in which young adults’ school-to-work transitions may be shaped structurally as they adapt to culturally diverse learning and work environments.