A recent study conducted by U.S. Department of Education (2018), noted that an alarming number of principals, close to 20 percent, left their positions, moved schools, or left the profession altogether. Next to the influence of direct instruction through a teacher, the principal is believed to have the most impact on student performance (Marzano et al., 2006) and efforts need to be made to retain these leaders in their respective roles. This dissertation study attempted to discover the unique challenges that the 21st century principal face, why principals may feel these challenges cause turnover and poorer wellbeing, and what support systems (internally and externally) currently exist or need to be created to allow experienced principals to extend their tenure in their current roles. A sample of elementary, middle, and high school principals, with a least five years of experience in the same building, were interviewed. Following the conceptual framework of Fullan's (2006) change theory methodology, this research provides strategies and support systems to create change and reflective practices for principals and their school organizations to increase principal longevity. A comprehensive analysis of the data was completed resulting in the following themes and sub-themes: challenges facing principals (challenges in the role, role changes), internal support systems (enjoyment from the position, methods to combat stress), and external support systems (school district support, training additions). Impacts on leadership, policy, theory, and practice are presented with a specific focus on mental health, professional development, and communication. Recommendations for internal and external support systems are offered for principals to extend their tenure and successfully traverse the challenges they face. [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.]