Purpose: The purpose of this qualitative multiple-case study was to explore and understand how women of color managed habits holding them back from becoming a high school principal based on Helgesen and Goldsmith's 12 habits. Methodology: The methodology of this study is a qualitative multiple-case study design to explore the experiences of women of color who are high school principals regarding the strategies they use to avoid habits that hold them back from promotion. A semistructured interviewing technique was utilized to obtain their stories. Findings: There were eight major findings that occurred throughout the data collection and analysis process. The findings revealed that women of color promote to high school principalships through engaging in holistic self-care, practicing self-kindness, self-compassion, and positive self-talk, being their own self-advocate, exposing their work to others, seeking growth opportunities and being a continuous learner, showing up whole heartedly, developing leaders and allowing them to be experts, and demonstrating effective leadership. Conclusions: The conclusions emphasized that women of color who are high school principals need to care for their physical, mental, emotional, and spiritual wellbeing to remain effective leaders. The conclusions indicated that women of color who are high school principals need to operate in their gifts of imperfection which are courage, compassion, and connection. The conclusions revealed that women of color who are high school principals need to develop other leaders, practice shared leadership, and allow others to be the expert. The conclusions asserted that women of color who are high school principals need to show up genuinely and authentically to build and maintain supportive relationships. Recommendations: Recommendations suggested that county offices and school districts invest in wellness programs for women of color who are high school principals. It is also recommended that school districts create mentoring and training programs for women of color who are high school principals. Additionally, the recommendations proposed that school districts provide spaces of healing for women of color and African American employees to overcome the harm of experiencing workplace bias, microaggressions, and stereotypes. [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.]