This dissertation engages a multi-step process to identify and articulate the internally defined goals of prominent holistic pedagogies including Montessori, Waldorf, Democratic Free Schooling, homeschooling, and radical/progressive education. It gives voice to adult former students who speak to, and illustrate, the ways in which they were impacted by their holistic educational settings on each of six identified areas of intended holistic development: physical, creative engagement, intrapersonal, interpersonal, cognitive, and transpersonal. Eighteen participants, ages 19 to 71, from various holistic backgrounds in North America, participated in focus group meetings and interviews. They reflected on their current sense of self on each aspect and discussed the pedagogical structures that they experienced as impactful on their development. Participants benefited from pedagogical structures that provided them with two key qualities: "non-interference" with the unfolding of their internally motivated curiosity and developing sense of self, and "freedom within structure" where their development was supported by capable and caring educators that gave them both leeway and boundaries. For participants in their early 40s and younger, the unique circumstances of their education, while providing them with acute levels of self-awareness and self-confidence, sometimes left them feeling ill-prepared for the social norms outside of their settings. The eldest participants described profound appreciation for their educational experiences, holding value systems and life histories that reflect a dedication to social justice and activism. The author's proposed "Theory of Holistic Wellbeing" (ToHW) asserts that assessing and supporting all six aspects of development facilitates the appreciation of the fundamentally interconnected nature of all that is and the prioritization of social activity for equity and the common good. Which, if done conscientiously and iteratively, is understood to support the holistic wellbeing of individuals, and ever increasing societal and planetary welfare and unity. [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.]