This formative intervention documents the emergence of a hybrid activity aiming at student engagement and academic achievement. In this context-bound study, early stages of this activity consisted in establishing PénArt meant to enable high school students with difficulties to start up their own business at school. It involved reaching agreements between a high school and a youth centre so that high school students engage in the production and selling of their branded t-shirt. At the frontiers of their respective activity system, students, youth workers, special education teachers and members of the school board took actions to cross boundaries and redefine their interrelations. Cultural historical activity theory was fruitful to document the development of a new object-oriented activity. Tensions and contradictions revelaled to be the key moments in the emergence of the hybrid activity. Expansive learning led us to understand that, in a conflicting situation, a collective's agentive actions create an expansive form of learning and leads to a successful entrepreneurship experience. Change laboratory capacity to foster change for cooperative education in Quebec was successful. The students enrolled in a regional entrepreneurship contest and won it. That was a significant event for students with low self-esteem linked with their performance at school.