There continues to be a discrepancy between women, who comprise 77% of the public school institution, yet make up only 31% of the superintendency and only 34% of high school principalships. This study sought to examine those very personalized, professional, and intimate connections of women who serve as a high school principal or superintendent in a district with a high school in suburban Chicago; I also examine how these women draw upon their support networks in applying for and achieving jobs, sustain them in their work, and garner support from professional organizations that help women find their personalized learning networks. This qualitative study interviewed eight women who are currently working in the education field, and who hold (or have held) superintendent and/or principal positions; the women were interviewed two times in semi-structured interviews. The findings support the need for women to find encouragement when applying for the formal roles of principal of a high school or superintendent in high school districts, and respondents identified various ways that both men and women encouraged them in their personalized learning networks. The participants in the study noted that they collaborated with their personalized learning network regularly as part of performing their formal leadership role. The findings showed there is not one right way to create a PLN network, and women look for very specific traits when including other women in the most personalized spaces. Traits they sought include authenticity, the capacity to be vulnerable, timeliness, supportiveness, and the ability to provide feedback. Women desire safe spaces to process information, especially that about the lived experience of being a woman with other women. This study provided a promising solution for closing the gap between women in men in key leadership roles but demonstrated that educational instructions at all levels must move beyond informal and inconsistent supports, putting into place formal and structured spaces to help women create the relationships they need, in order to be more likely to take on these demanding jobs and to better serve our profession and our students. [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.]