This paper will focus on a discussion of three concepts; trajectories, transitions and transformations. The paper will present a particular configuration of these concepts which presents a life course approach to work / learning transitions. This approach can be deployed with existing workers, those in precarious employment and those wishing to re-enter employment and / or re-engage with formal learning. Firstly the changing nature of transitions and transitional types will be discussed before exploring research involving learning identities and learning trajectories; (Gorard et al 2001). The notion of transitional labour markets (TLMs) and its implications for post compulsory education and training provision (Schmid 2002; Ziguras 2005; Anderson 2005) will then be discussed along with the pedagogic approaches of ‘biographicity‘ (Alheit, 2002) and transformative learning designs (Mezirow 1991). The lifecourse approach to work / learning transitions presented calls for an expanded understanding of the different types of transitions and the crucial role of identity (vocational and learner) in navigating these transitions. The paper will challenge the dominant conceptualisations of learning / work transitions and examine the restrictive structural factors within Australia’s education and training system, which inhibit successful transitions especially for those groups at risk of marginalisation in the changing labour market.