Careers work in the twenty-first century faces a key challenge in terms of digital technologies: to evaluate their potential for careers work in challenging settings. Given the rapidity of developments, technologies require evaluation in research innovations and naturalistic settings. Virtual worlds offer potential for careers and guidance work, and the therapeutic domain. To illustrate this, we present examples in which young people explore their feelings and ideas, plans and difficulties, while preparing for film-making. During this they develop important life transition skills. We argue that the power of virtual worlds--to support emotional and cognitive engagement--could be utilised in practice settings. We conclude that they are serious candidates as digital tools in the careers and guidance domain.