The OE is a working holiday phenomenon in New Zealand that shapes the life experiences of many young adults. "Should I stay or should I go?" critically engages with this social phenomenon by approaching it as simultaneously an opportunity for freedom and choice and a field of rules, regulations, and constraints. The analysis of the OE offered in this thesis draws on Foucauldian understandings of power and discourse and, more particularly, Nikolas Rose's approach to governance through freedom and the constitution of subjects in advanced liberal democracies. By using these theoretical resources, it investigates how the OE is discursively constructed as a life course experience through which power operates via the promises of freedom and choice. A combination of substantive resources, including existing academic literature, print and virtual media, questionnaires, web-based discussions, and conversations with young New Zealanders planning to pursue an OE are used to illustrate how many of them are governed as they embrace the freedoms associated with the OE. The use of Foucault facilitates an understanding of the discourses through which young New Zealanders are constituted and constitute themselves as OE travellers. Attention is also paid to the ways in which the actions of authorities - governments, non-state organisations, and commercial travel operators - contribute to the regulatory environments and social imaginaries that shape young adults' experiences of the OE.