This article examines the concept of transformative learning, with a focus on the importance of trans-disciplinary thinking (cognitive skills that cross disciplines) and new technologies in creating 21st century learning and transformative teaching. The article introduces the Technological Pedagogical Content Knowledge (TPACK) framework as a way to develop the specialized knowledge, skills, and understanding that teachers must have to become effective classroom constructors of transformative learning experiences. The authors note seven cognitive tools needed for success in the new millennium, within this TPACK framework. To illustrate and describe these skills, they offer examples of how teachers can repurpose digital technologies to use these thinking skills toward building exciting transformative learning experiences, across a variety of subject matters. The authors explore the implications for research and practice. (Contains 1 footnote and 1 figure.)