Since the Great Financial Crisis (2007–08) many countries have explored how education systems can better prepare students for their working lives in order to reduce youth unemployment and enhance educational engagement and achievement. This paper focuses on Career Pathways, learning programmes delivered in general secondary education that allow students to undertake a deep exploration of a vocational field of interest while keeping their options for the future open. In a first-of-its-kind analysis and building on understanding of historic provision, the study considers innovation in programme development in five predominantly Anglophone countries (Australia, Canada, New Zealand, Scotland and the United States) since 2010. While historically participation in Career Pathways has been strongly associated with better employment outcomes for learners, evaluations have highlighted important challenges to their delivery at scale for the full range of learners. This paper reviews a range of responses to historic challenges based on study visits to five countries and closes with policy recommendations for future enhancement of provision.