In this article the five career narratives of three siblings and two unemployed men are drawn upon to critically examine the use of contemporary career discourse as a means to negotiate changes to work since the 1980s and to the present time. A critical analysis enables contemporary career discourse and workplace change to be located with in the historic, sociopolitical, and economic context. The five career narratives could be described by drawing upon various contemporary career models. However, these models failed to account for the participants' less optimistic experiences. Their experiences are micro level examples of macro level trends associated with structural adjustment programs, organisational restructuring, and increased global competition. Careers theorists, practitioners, and administrators are in a unique position to become proactive in drawing political attention to the less positive outcomes of workplace change. Changes to the shape of work over the past two decades have been well documented. Concomitant developments in career theory incorporate these changes by expanding the boundaries of career to include a variety of employment patterns and non-work aspects of life. Such understandings deem that each individual has a unique career. The ensuing prescriptive and constructivist career management models provide guides for designing and interpreting career. Indeed, improved individual and societal wellbeing, as well as reduced costs to individuals, organisations, and the state, have been attributed to properly managed careers (Greenhaus, Callanan & Godshalk, 2000). These espoused benefits have prompted many governments to fund careers service agencies to facilitate the achievement of welfare, education, training, and labour market policies (Watts & Fretwell, 2003).