|Abstract||This qualitative intergenerational study explores the life of the author and his family of educators. The study goes back four generations to look at the influence that family, social norms, opportunity, religion, and other factors played in a disproportionate number of family members entering and spending their careers in Texas public schools. While each participant followed their own unique path into the field of education, family influence remained a signficant factor for each participant. The family of colleagues provided instructional and emotional support to participants once they entered the field as well as serving as a recruiting tool to those who were not yet educators. This study also follows the author's journey toward a greater understanding of himself as the origins of his perceptions and beliefs are uncovered through the storytelling of family members. He is able to explore his thought process as he uses the study's findings about his family to trace back the origins of influences on his ways of thinking, feeling, and decision making. The author also explores how this knowledge will help to guide his future decisions as a public school administrator for the benefit of the students, staffs, and communities he serves.