This article uses metaphors to explore how changes in technology and the world of work affect the lives and identities of workers today. The author integrates theory from vocational psychology and cultural studies with personal narrative in order to consider positive and negative aspects of the shift from traditional linear careers to postmodern, boundaryless, protean careers. Career is framed as a dialogical construct that is mutually shaped by individual and social practices. Career counselors are invited to consider ways they might adapt their practice to better accommodate clients' lived experiences of evolving career contexts.