Abstract: The purpose of this phenomenological inquiry was to investigate the lived experiences of high school veteran teachers who transformed their teaching methods from traditional 20th century instructional practices to facilitating the development of 21st century skills in their students. Interviews with the seven participants were analyzed in order to understand the essence of their experiences. The researcher concluded participants’ beliefs and expectations, regarding their role as a teacher, were critical to their commitment to change their instructional paradigm. In addition, they required support from others, such as colleagues, supervisors, and technicians, to successfully transition to 21st century pedagogy with digital tool integration. The transformation of instructional practices was consistent with Mezirow’s (1991) transformative learning theory. Implications for practice include recommendations for teacher training, preparation, and on-site support, related to digital tools.