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 their students in developing 21st century skills. Interviews with the seven participants were analyzed in order to understand the essence of their experiences (Lincoln & Guba, 1985; Moustakas, 1994). The researcher concluded that the 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. These teachers' transformation of instructional practices was consistent with the components described in Mezirow's (1991) transformative learning theory. Implications for practice included recommendations for teacher training methods, with regard to utilizing digital tools in the classroom, and appropriate on-site support. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]