In a world dominated by change and transformation, this article explores instructional technology connections to and applications of transformative learning. The author provides an overview of the theory of transformative learning, which embraces the hallmarks of 21st century learning. Rather than focusing solely on how to use technology, transformative learning emphasizes the learning process, including, but not limited to, problem solving, reflection, critical thinking, and dialogue. From this orientation, the article provides a foundation for what can be included and recommendations for pedagogical choices of instructional technology. Moreover, one recognizes larger connections among these goals and workforce readiness, college readiness, lifelong learning, career success, and life coping skills. The author raises questions which reach beyond traditional instructional technology orientations, assessments, and outcomes. (Contains 1 table and 1 figure.)