The COVID-19 pandemic, political polarization, and racial reckoning are but a few of the challenges faced by U.S. independent schools and their heads today (Bassett, 2010; Juhel, 2016; Rowe, 2021b). This basic qualitative study sought to understand the challenges facing heads of U.S. independent schools and how these challenges inform heads' perceptions of their roles. 22 independent school heads who led schools since 2018 participated in semi-structured individual interviews. Participants described their initial perceptions of their role when they first assumed their positions, the leadership challenges they have faced during their tenure, and the ways in which tackling these challenges has informed their evolving understanding of their role. Because independent school heads today are leading their schools through unprecedented challenges as well as more common challenges like enrollment management or fundraising, this study utilized Heifetz's adaptive leadership theory (1994) as a lens to examine how independent school heads perceive their role. Three findings emerged from this study. First, regardless of background or experience, participants did not know the full scope of the role of a head of school before they assumed the headship themselves. Second, independent school heads face many challenges in their roles; some can be solved with existing expertise, many require leaders to mobilize people to change their hearts, minds, and behaviors, and some are internal and require heads to alter their own mindsets to solve. Nearly all of the challenges heads face in their jobs, however, involve navigating relationships among constituents. Last, the study found that heads gain a fuller understanding of their role over time and while they are doing the job. This study includes recommendations for current and aspiring heads, independent school boards who hire and support heads, and independent school leadership preparation programs, as well as recommendations for future research. [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.]