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Current national and state education policy directions support the view that before students leave school they should have employment related skills and an understanding of the work environment and career options and pathways to further education, training, employment and lifelong learning. The 'School to work' program for secondary schools in New South Wales (NSW) is one of a wide range of programs within the NSW Government's education and training policy. This paper gives an overview of the Program, including anecdotal evidence from students and teachers. While the program has been successful, there remain challenges to be overcome. These include: that vocational learning needs to be embedded in the learning culture and practice of educational institutions and communities; that vocational learning needs to be recognised and valued by all educators; that educators, employers and the community need to work as collaborative partners to support vocational learning in schools; that teachers, through training, need to be well prepared and equipped to support students; that the professional development that enhances the skills of existing teachers and leaders needs to be strengthened; and that government and school authorities need to accept responsibility for the provision of adequate funding and support.