For decades the American public education system has struggled to meet the needs of our nation's children and families. In an effort to bring fresh solutions to this major issue, a trend of enticing accomplished private sector individuals into the education sector has developed within the past decade. The Broad Residency was established in 2002 to support this bolstering of human capital by supporting career transitions to education for accomplished leaders from business, law and the military to support the systemic changes desperately needed. A relatively new trend, there is little research on this topic. To better understand the specific transition from business to education administration through The Broad Residency, I use this study to learn (1) how Broad Residents experience the transition and (2) if there is a difference in this experience for individuals with different backgrounds, specifically management consulting or working for a corporation. To answer these questions, I interviewed twenty graduates of The Broad Residency who are currently working in urban public school district administration in ten urban districts from west to east coast. I examined over thirty hours of interview transcripts and identified themes in the areas of "fit" in terms of skill set and expectations of the culture of the work environment, as well as the challenges transitioners face and the supports they need to be successful to maximize their contributions to the field of education. This helped to develop an understanding of how these individuals experience their transition. Interviewees painted a picture of a career transition fraught with a multitude of challenges and sparse supports in place to meet the high demands of education administration work. I also discovered that some of the experiences differed based on an individual's background. Regardless of background, however, with plentiful challenges and minimal supports, feelings of success are still possible. This paper further describes in detail what these business-to-education administration transitions entail. It also offers conclusions and advice to individuals making the transition, as well as to organizations and school districts to make the most of these individuals' unique contributions to the sector. [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.]