To make the transition to adulthood, youth must learn to function in the complex and unpredictable "real world" of adult life. This is an intensive case study of an urban arts program that sought to provide youth with experiences that prepared them for the real world of arts careers. We conducted 75 interviews with 12 youth and their adult leader over three cycles of engagement with the real world. Analyses suggest that participants experienced a developmental process that entailed experiences of dissonance and challenge followed by active adaptive learning. The adult leaders played a critical role in supporting this developmental process through balancing to maintain an approximate fit between the challenges youth experienced and their abilities to respond to these challenges. (Contains 2 notes.)