This paper explores the concepts of vocational imagination and labour market literacy, arguing that these are important elements in the crafting of effective education-employment linkages. Evidence of truncated understandings of both is found in the talk of 93 young New Zealanders in transition from secondary school to their post-school lives. We argue that development of labour market literacy and vocational imagination requires that young people crafting career pathways are able to work on identity formation, to discover and develop their abilities, and to recognize relevant opportunities and constraints, all within an infrastructure that allows clear career pathways to be mapped. Changes in New Zealand's economic and educational landscape, together with forms of career education that are ill-matched for this developing landscape, have inhibited such an approach and so contributed to the truncation observed. We suggest that this analysis points to ways of enabling young people to make links between education and employment more effectively. (Contains 3 notes.)