Researchers argue that much of who we are is developed during childhood. Childhood relationships and developmental activities, opportunities, and experiences (including hardships) come together to create each human being. Yet, little exploratory research has been conducted regarding the childhood experiences, activities, personalities, and perceptions of successful leaders. In-depth, qualitative interviews with ten women university presidents were conducted to investigate perceptions and experiences related to the lifetime development of leadership skills, abilities, and competencies. The lived experiences of these women were investigated using the phenomenological research methodology so that “voices” could be heard and unique insights examined. This paper explores a portion of this research focused on the childhood experiences, characteristics, and memories of women university presidents as they directly and indirectly relate to the development of leadership. It specifically centers on childhood personalities, school and other activities, influential individuals, and significant events and challenges. Results support the growth-task model of human development. As children, the presidents were generally obedient, reflective, observant, smart, self-directed, competitive, and moderately to highly confident. It was important for them to live up to their own expectations as well as those of significant adults around them. These women participants were involved in a variety of helpful activities as children and thrived on learning and developing new skills, knowledge, and capabilities. Other than their own parents, influential individuals during childhood included predominantly women (elementary school teachers, aunts, and grandmothers). The most helpful learning experiences involved challenging and difficult situations or events (e.g., illness, relocation, and fear).