In order to maximize college English language students' learning, product development, 21st Century skills and engagement with real world meaningful challenges, a course was designed to integrate Challenge Based Learning (CBL) and iPad mobile learning technology. This article describes the course design, which was grounded in design thinking, and provides an overview of the pilot implementation of the course. The course achieved its goals to a great extent in that learners felt that they were beginning to help build a better college community by sharing stories of their learning experience and their insights about the essential question they chose with other students and with other teachers. The course also helped the students discover the use of English as they found ways to reach out to the broader college community and held meaningful conversations with teachers, librarians, managers, and staff from different departments and other students. The course transformed the teacher/researcher into an observer of learning and a guide, thus flipping the classroom and allowing the learners to take responsibility and steer their own learning experiences. Further development is needed in the areas of CBL assessment rubric development in English Language Teaching (ELT) and the analysis of student generated content through iPad applications. (Contains 1 table.)