Global organizations and institutions have long recognized the skills and dispositions of design and social entrepreneurship as a means to respond to the volatility of our times. And yet, our education system has been very slow to integrate these ways of thinking and doing into the learning environments of young people. In this interactive workshop, we will explore the ideas of the pragmatic imagination, extreme learning, and learning ecosystems, all of which place the learner, design, and social entrepreneurship at the center of the learning experience.