The principalship has one of the worst job turnover rates in the nation and continues to get progressively worse. Fifty percent of principals leave their positions by their third year (Goldring & Taie, 2014; Superville, 2014). This is a serious problem in education because next to teachers, principals have the second biggest influence on student achievement. The purpose of this qualitative study is to understand the challenges principals face that contribute to their departure from the principalship and to identify conditions that encourage principals to stay in their positions. Most of the research on principal turnover is limited because it examines the problem of principal turnover through one lens or perspective. This study utilized Bolman and Deal's Four Frames (2008) as a theoretical and analytical framework to obtain a comprehensive understanding of principal turnover and retention. Bolman and Deal defined the four frames as structural, human resource, political, and symbolic. Ten principal respondents participated in this study by providing their perceptions of the principalship in semi-structured interviews. Their contributions yielded rich data that supports and adds to the literature on principal turnover and retention. There were several implications from this study in each of the four frames that have the potential to improve principal job satisfaction and principal retention. Implications in the structural frame include hiring individuals that enjoy the unpredictable nature and role diversity of the principalship, providing more principal training in special education, understanding the additional challenges school of choice presents for principals, and the importance of developing crisis management plans. Key implications revealed from the findings in the human resource frame that can improve principal job satisfaction and longevity include ensuring elementary principals have a competent and supportive office staff, providing opportunities for principals to work with principal colleagues in their district to learn from each other's strengths and to mitigate isolation, providing competitive pay, encouraging principal work-life balance, and recruiting and supporting female principals into secondary principal positions. Political implications revealed from the findings include helping principals establish positive and collaborative relationships with union representatives, ensuring that principals are not reliant on parent-teacher organizations for funding their school goals, and helping principals navigate through the current political challenges. Implications revealed in the symbolic frame include providing principals with support and training to create a healthy school culture, providing training and support on handling negative social media postings, and helping principals with culture problems associated with a crisis, such as COVID-19. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]