Drawing from American history, fashion design, history of luxury, visual culture, museum studies, and women’s history, among others, this book explores the challenges, rewards and benefits of teaching business and the labor history of art and design professions to those in higher education. Recognizing that artists and designers are no longer just creatives, but bosses, employees, members of professional associations, and citizens of nations that encourage and restrain their creative work in various ways, the book identifies a crucial need for art and design students to be taught the intricacies of these other roles, as well as how to navigate or challenge them. This empirically driven study features case studies in various pedagogical contexts, including museum exhibitions, group projects, lesson plans, discussion topics, and long-term assignments. The chapters also explore how the roles of designing and making became separated, how new technologies and the rise of mass production affected creative careers, the shifts back and forth between direct employment and freelancing, and the evolution of government interventions in creative fields. With a diverse and experienced range of contributors, and providing a unique set of conceptual tools to interpret, cope with, and react to the ever-changing conditions of capitalism, this volume will appeal to educators and researchers across education, history, art history, and sociology, with interests in experiential learning, capitalism, equity, social justice and neoliberalism.