There exists a cognitive dissonance between the current state of educational delivery systems and the preparatory needs of the non-traditional student who desires a professional life outside of the cultural norm. The aspiring professional painter, musician, poet, actor, novelist, photographer, or dancer all fall into an educational category that is not properly served by current pedagogical design at all levels. In order to address this problem of practice we must first identify common themes present in a non-conformist, entrepreneurial life progression though the formative years. To that end I will begin with a presentation of my own story, which encompasses all of the critical phases of the journey travelled by a professional artist. The overall objective is to illuminate each challenge faced by the singular artist as they progress though the phases of life and career. Then, utilize the discoveries to suggest alternative adjustments as to how this segment of the population can be nurtured and supported. [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/en-US/products/dissertations/individuals.shtml.]