This purpose of this research is to understand how young adult homeless working men experience homelessness in an oil boom and prosperous city, Calgary, Alberta. Following a period of participant observation, five purposively selected working homeless men aged 20-28 years participated in in-depth individual interviews, which were initiated around their daily food routine. We found that the men experienced moderate to severe food insecurity and reported negative physical health effects, including weight loss, related to their inability to acquire sufficient food to meet work demands. The interviews led to other findings: the men accepted full responsibility for their homelessness, internalized hegemonic ideologies of self-blame, and praised Calgary as a great city, in dissonance with their experience of discrimination and privation. The working homeless men also negotiated their identity through unspoken honour rules and through the construction of an informal system of resources and social networks. Although service providers were described as abundant, the men did not claim any meaningful interactions with them. Our findings suggest that efforts to address homelessness need to consider food needs related to accessible and adequate nutrition for sustaining work but also the ways in which working homeless men see themselves and view their homelessness as they navigate their day-to-day survival.