This study explored private school principals' career outlooks because of their critical role in shaping academic environments essential for student success. Principals face multiple challenges that can affect career decisions. Employing an electronic survey, this quantitative study included 65 current private school principals, collecting data through the Non-Public Head of School Index of Motivators (NPHSIM). The primary research inquiry examined the elements that affect principals' career choices, encompassing their motivations to continue in their current positions, pursue advancement, retire, or transition to different careers. Additionally, it considered demographic factors impacting career perspectives, including gender, educational qualifications of principals, the grade levels they oversee, affiliations with religious institutions, and the geographical context of their schools. The survey included Likert-scale and open-ended questions to gather comprehensive insights into participants' experiences and perceptions. Results from the analysis suggested trends in the motivations behind career decisions among private school principals. The role of faith-based administrator became central to the results because of the participants' positions. Research findings reveal that private school principals emphasize servant leadership, which is grounded in several fundamental principles: the capacity to share personal faith with both staff and students, a foundation rooted in faith, the effectiveness in implementing change, the ability to articulate a personal vision, and the provision of administrative and leadership support. The findings of this research are associated with elements of individual motivation. The motivation theories proposed by McClelland (1987) and Maslow (1943) were examined with one another to investigate the career aspirations of private school principals. The Affiliation factor identified by McClelland consistently ranked highly among these leaders, indicating that their professional paths are largely influenced by a strong inclination to foster positive interpersonal connections. Additionally, private school principals emphasize their faith, which significantly informs their professional choices. In contrast, public school principals are primarily driven by factors such as career progression, financial incentives, support from central administration, and opportunities for professional development, aligning more closely with McClelland's Achievement factor. By highlighting what drives these educational leaders, this study contributed valuable information that can inform strategies to enhance private school principals' professional experiences and ultimately improve school climates. This research underscores the importance of understanding private school principals' personal and professional aspirations, offering a pathway to support their sustained engagement in educational leadership. [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.]