In this podcast, I talk about two aspects that affected interview participants’ studies overseas. Funding and military service put young Singaporean men in a position of obligation, but while some people react with strategic consent or outright support, others find ways to resist or negotiate their positions between the state and family welfare. The transition from military service to looking for financial support for international tuition fees can be challenging. I discuss some participants’ perspectives on the challenges they experience in pursuit of the Singaporean dream.