For Latina school administrators, the movement through the principal pipeline is not easy, as many encounter discrimination and biases rooted in their gender, ethnicity and other intersecting identities. Schools should leverage Latina administrators' cultural knowledge, perspectives, and experience to improve student educational outcomes. A Latina administrator brings these prior experiences to the work and can better understand and support the needs of the growing Latino/a population (Crawford & Fuller, 2017; Elizondo, 2005; Magdaleno, 2006; Mendez-Morse, 2004; Mendez-Morse, & Byrne-Jimenez, 2016; Murakami, Hernandez, 2016; Rodriguez, Martinez, & Falle, 2015). The dissertation highlights four Latina administrators' personal and professional journeys as they navigated the principal pipeline through interviews. Through participant and mentor interviews, the researcher sought to uncover the challenges, triumphs, and support systems the Latinas faced during their trajectory. The dissertation highlights participant stories with the objective of understanding how they overcame challenges and barriers with mentorship support. Latina representation is crucial, yet Latinas are scarce in leadership roles (Bitterman et al., 2013). Importance must be placed on actively developing a diverse group of Latina administrators, to ensure school leaders are better equipped to understand and address the academic challenges and disparities faced by Latino/a students due to their shared cultural backgrounds and experiences. The framework for this dissertation, Latina/o Critical Race Theory, or LatCrit, (Solorzano & Bernal, 2001), encompasses a range of social constructs such as racism, classism, sexism, and other forms of oppression that exist within the lived experiences of Latino/a administrators. As LatCrit is explored, these four Latinas' experiences showcase how social constructs intersect with their individual journeys. The findings revealed that while the four Latinas navigated their pathways to the principalship, they found empowerment through mentorships. They drew strengths from their identity and their mentors, took on a "Si se Puede" mindset and pursued their Calling, or "Vocacion," and became principals. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]