A generative individual guides, cares for, and invests in the next generation and, by doing so, creates and constructs a legacy. Not every person is purposeful in their legacy, but each person will leave a legacy, regardless of their intent to do so. An educational leader’s focus on generativity and legacy may have a connection with achieving meaning in life through meaningful activities, personal experiences, and attitudes. It is highly likely that an educator already participates in generative expressions by passing on ideas, values, traditions, knowledge, and things that outlive themselves. The problem at hand is a lack of research and linkage between meaning in life and generativity and legacy, specifically for educational leaders in faith-based schools. The current study explored leadership expressions of generativity that may result in meaning in life or leaving a legacy. It is a qualitative study that utilized a multiple-case study design to assess three faith-based schools with diversity in geographical region, school longevity, school size, and distinct model variants. The sample frame included three cases with three variants of educational leaders within each case: administrative leaders, classroom teacher leaders, and parental educational leaders (N=18). An alumni focus-group discussion was also conducted. Each educational leader answered questions related to their own meaning in life, generativity, and legacy in an educational setting. The research goal endeavored to answer the following question: “In what ways do educational leaders leave a legacy with their followers in K-12, faith-based, University-Model® schools?” Findings showed that faith-based educational leaders exercised their callings and purpose with numerous generative expressions that led to meaning in life and a future legacy.