In recent decades, young people's transitions from school to work have undergone substantial changes. As young people make their way from compulsory schooling to employment, they find themselves having to navigate an increasingly complex, technologically innovative and globalised world. These social changes have prompted youth researchers to reexamine young people's transitions within the life course while paying particular attention to different contexts and risks young people encounter. As part of this reexamination, this article develops a conceptual framework that attempts to capture some of the complexity inherent in young people's decision-making regarding school and work within the context of a boomtown--Fort McMurray, Alberta, Canada. The rapid growth of the oil industry in Fort McMurray has produced an environment where young people must make decisions about school and work within the context of a rapidly growing city with an overabundance of jobs. Drawing on interviews with young people from across the school-to-work transition, this article demonstrates the range of complex factors that young people consider in their school and work decision-making. In particular, this article emphasises the importance of considering the different degrees that young people demonstrate agency and reflexivity.