Recent decades have seen an exponential growth in the field of international schools, and a concurrent rise in the number of young Anglo-Saxon teachers overseas. Such mobile teaching careers have largely been presented in terms of emphasising exploration, travel and lifestyle-related migration. While acknowledging such factors, we also draw attention to financial constraints, and in particular, to the challenge of personal debts, which weighs heavily over many Anglo-Saxon teachers. We therefore discuss international teachers' mobile trajectory in terms of a balancing act of negotiation between lifestyle and financial factors and point to a strategic trade-off between the two. Moreover, by emphasising the neglected aspect of indebtedness, we argue that, while a key point of appeal for such teachers' participation in the international school sector lies in the ostensible participation in the carefree, privileged environment of lifestyle migration that would have been out of reach for them otherwise, in reality, such horizons of opulence are limited, as teachers are locked into a precarious system that offers little protection and is highly unpredictable. In this context, the accumulation of professional experience provides only a limited pathway for assuming control over one's future destiny/destination -- be it professional, geographic, or financial -- and at times may even backfire.