Most creative aspirants from working-class and minority backgrounds have grown up in places remote from the epicentres of the creative economy, and must undertake journeys if they are to fulfil their life plans. Such journeys are archetypal – the stuff of youthful fantasies – but they can provide both economic and social challenges. The journey forms part of the classic Bildungsroman narrative of the passage from adolescence to maturity. It is not just geographical, but also social and cultural. It can require aspirants to remake themselves, to change their image, in order to fit in with new urban scenes. The informal and improvised relations of the new economy mean that to be seen as cool or hip is not only important for accessing particular peer social groups, but also the networks through which vocational opportunities are allocated. In this chapter we argue that, far from being the egalitarian sphere that some have suggested, the new economy can actually accentuate existing power relations and sources of disadvantage. Those who are deemed not worthy rarely get far and the social and economic costs associated with ambition can be high. Our interviewees, most of whom grew up in Sydney's western suburbs, generally experience their neighbourhoods/ communities as places of comfort, but also of cultural sterility, as lacking the dynamism of the creative scenes and networks that operate in the inner city. The metropolitan journey therefore appears to be crucial if they are to break into those scenes and networks and access the opportunities that might lead from them. While to the greenhorn the journey appears to offer the chance for magical change, the experience can often be demoralizing. We will look at the cases of two young women, Nada and Tanja, who, after receiving lucky creative career breaks, experience a sharp sense of cultural vertigo, of being out of place and inadequate, in their new workplace settings. With the metropolitan journey comes the pressure to make unpalatable sacrifices.