This article investigates the life experiences of 19 young people on the streets of Pelotas, southern Brazil. Manifold methods were used revealing several highly interconnected aspects in their realities. This study, which was conducted for a period of seven years (2009–2016), illustrates how the studied street youths form their environments physically, socially and mentally in order to reach their goals and create the multiple means of survival in challenging street environment. It is important to understand heterogeneous, interrelated physical, sociocultural and mental elements to study subjectively experienced realities. Personally experienced multidimensional constraints and incentives and the individual’s own goals shape these realities.