This study narrates the role of education/training in the career success stories of twelve women on an Irish active labour market programme, Community Employment (CE). All from lower socio-economic groups, having early school-leaving backgrounds, and, prior to CE, were long-term unemployed. CE enhances the employability of the long-term unemployed by offering job opportunities and providing education/training. Using narrative inquiry, it understands how the women (re)construct their interpretations of their career success following critical moments of change in their lives. The study narrates the stories on a case-by-case basis according to the category of critical moment that each participant experienced and then views the chronicles via the lens of social class as mediated through the educational structure. It, therefore, specifically recognises the micro-individual and macro-social aspects of a person's interpretation of his/her career and education/training experiences. To understand the change process inherent in the stories, a theoretical construct, Giddens' (1991) fateful moment, is operationalised by examining how the critical moments evolve in to fateful moments facilitated by the structural influence of the education/training provided by the expert system of CE. The study concludes by proposing three categories of career success for this sample to take account of their altered career structures.