There is a shortage of literature containing the principal's voice and articulation of her or his journey through leadership. This exploratory research extends the understanding of the nature and meaning of the lived experiences of the Generation X cohort within the context of school principals and assistant principals leading in 21st century schools. This qualitative hermeneutic phenomenological study explored Generation X school principals' and assistant principals' experiences leading a multigenerational workforce. A multigenerational workforce is defined as comprising of employees from five different generations: Traditionalists, Baby Boomers, Generation X, Millennials, and Generation Z. The researcher sought to explore (a) what aspects of Generation X school principal and assistant principal education, training, or development helped them prepare as a school leader; (b) how Generation X school principals and assistant principals describe and enact their leadership style(s) to lead a multigenerational workforce; and (c) how societal context has influenced Generation X principal and assistant principal leadership (i.e., Global Pandemic, social and emotional health concerns). Three global themes emerged from semi-structured interviews with 15 Generation X school principals and assistant principals in a public school district: Identity, Flexibility and Adaptability, and Social Awareness. The findings indicate (a) participant identity for these participants is multifaceted and informed by culture and social interactions, (b) Generation X leaders are flexible and adaptable, and (c) Generation X leaders utilize social awareness and societal context to foster equitable and inclusive learning environments. This research highlights the experiences of an often overlooked generation to help these Generation X leaders reflect on the ways their adolescent experiences influence the way they currently lead a multigenerational workforce. [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.]