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The Enterprise & Career Education Foundation (ECEF), formerly the Australian Student Traineeship Foundation (ASTF), was established with funding from the Australian Commonwealth Government to promote opportunities for young people to gain workplace knowledge and experience before graduating from secondary school. This paper aims to provide insight into the issues involved in youth transitions from school to work, youth employment and the ECEF's structured workplace learning program. The paper contains a review of the most recent international and Australian literature in the areas of youth employment and education, youth transitions, school-industry programs, and structured workplace learning. Key findings are that: (1) young people in Australia have become better educated; (2) early school leavers are severely disadvantaged in the labour market; (3) Australia has a high rate of school leavers combining part-time work and study in their initial postcompulsory years; (4) youth employment and earning levels have fallen despite strong economic growth, with teenage unemployment being high in comparison with other Organisation for Economic Co-operation and Development (OECD) countries; (5) the transition from education to work is smooth for most students; (6) there has been a significant growth in the number of schools offering school-industry programs; (7) most parents support school-industry programs; and (8) structured workplace learning helped most young people into work or further education. The paper also highlights the six features of successful transition systems identified by the OECD and recommends that vocational education and training (VET) and enterprise education be integrated into the education system in Australia.