The rise of the Internet and the resulting social, commercial, and entertainment platforms have enabled a digital economy in which youth are participating as they develop a range of sociocultural practices. As young people engage in a greater variety of leisure activities online that create value such as gameplay, media production, and content circulation, the boundaries between work and play are sometimes blurred. While the new networked platforms may provide youth with beneficial new means of expressing themselves, learning, and connecting to others, they can also be used in ways that allow youth to earn income. Inspired by the dynamics of the emergent networked environment, this project examines how youth regard the changes to their current play and their future work. Building off of the team members’ strong background in law and regulation, media analysis, and connected learning, the project looks at related policy challenges and how a multi-stakeholder effort can help create a future that both encourages the entrepreneurial spirit while also ensuring fair labor practices and equity.