This study investigates the reasons why Working Holiday Makers (WHMs) in Australia decide to complete the 88 days of specified regional work to obtain a Second Working Holiday (WH) visa. The research follows a qualitative approach via the use of semi-structed interviews on a sample of fifteen current or former WHMs. The resulting data are analysed in connection to the theoretical framework of migrants’ role in bifurcated labour markets, with a further focus on the micro-level neoclassical economics principles and the concept of self-improvement through hardship. It is argued that the 88-day scheme represented for all the interviewees a form of investment to achieve a greater goal. The findings revealed that, while only a few completed the 88 days driven by the desire to achieve self-actualisation, most of the informants were driven by an economic rationale: some focused on the short-term financial benefits of a further year of work in the country, while others planned to use their Second WH as a pathway towards permanent residency.