A cohort of 15 participants was chosen to engage in a study to identify a relationship between personality type and the propensity to choose professions in student affairs. Participants were chosen based upon specific demographic criteria in an effort to highlight inconsistencies in traditionally accepted variables, including gender, ethnicity, socioeconomic status, and "first-generation" designations. All participants were female, of Other ethnic origin, middle-class, and the first in their families to complete graduate-level degrees. They all currently work in various student affairs positions at the same higher education institution, and participated in the study in three phases. First, Riso and Hudson's (1999) Quick Enneagram Sorting Test (QUEST), readily available online, was used as a pilot to predetermine personality type. Second, a Typing Interview was used to substantiate the qualitative inquiry component of the study, including theories pertaining to deconstruction, stage development, personality, spirituality, leadership, feminism, positive psychology, organizational culture, and professional development. The third and final phase included completion of Riso and Hudson's (1999) Riso-Hudson Enneagram Type Indicator (RHETI), which was administered to all participants to determine their most probable personality types. A relationship between the Enneagram's personality Type Two: The Helper and the choice to work in student affairs was identified, with substantive support from the variables and theories explored throughout the study. [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.]