This study examined the change in conditions over time for Asian American Pacific Islander (AAPI) principals as they pursued a career as principals in the K-12 system in Los Angeles Unified School District. I compared the perceptions, motivations, and aspirations of AAPIs who became principals from 1970-1989 and from 2000-2011 to explore the change over time in the reasons as well as factors that supported or hindered them as they negotiated their career from teachers to principals. It was hoped that the findings from this research would assist policy makers and administrative leaders in better supporting the next generation of AAPI principals in order to maintain equal representation of AAPI students to AAPI principals. The sample was comprised of five principals from 1970-1989 and 15 principals from 2000-2011. Using a qualitative research design, I collected data using a short demographic survey, writing prompts, and face-to-face interviews. My findings showed that some reasons and factors stayed the same regardless of time, some manifested themselves stronger in one group over the other, and some existed in one group while being absent in the other. Themes that emerged for reasons they pursued a career as principals included high respect and satisfaction of pay in the teaching profession, preference for humanities related majors in college, and personal confidence. Factors that were considered for either supporting or hindering their process of becoming a principal included cultural values, homophily, environment of their time, availability of resources, and pressures of family care. The findings of this study led to recommendations for supporting AAPIs in the future to maintain their representation in the district. [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.]