Experiences in workplaces and educational institutions can both potentially be generative of rich vocational learning. That is, learning that has the capacity to be effective in the circumstances of its acquisition and be utilised in settings beyond those in which it was secured. It is worth noting, that this goal of extending the utility of what is learnt is both a key claim of and rationale for the existence of educational systems and institutions. Similarly, understanding how best to utilise workplace learning experiences and augmenting them with intentional experiences in workplaces and vocational educational institutions stand as important bases for improving vocational learning. Whether considering the initial skill formation through apprenticeship-type arrangements or vocational education provisions based in schools, vocational colleges or universities, the consistent and abiding goal is to generate rich vocational knowledge for learners. The educational purposes to be realised through such rich learning include: (a) assisting understand the requirements of working life generally (Ghost, 2002), (b) developing occupational-specific knowledge (Australian National Training Authority, 1993), (c) understanding the particular requirements for a selected occupation; (d) variations in the requirements for that occupational practice (Billett, 2001a), (e) providing experiences to critically appraise the world of work (Billett, 2006), and (f) the capacity for developing general workplace competences, as in core competencies (Mayer, 1992; The Secretary's Commission on Achieving Necessary Skills, 1992). However, to secure these distinct kinds of educational goals, through integrating experiences in workplace and educational institutional setting requires particular kinds of curriculum and pedagogic practices to be enacted. Offered in this chapter are instances of and suggestions for helping workers as learners and vocational students understand the world of work and the development of specific vocational competence.