This quantitative study examines the correlation between measures of subjective career success using an independent samples t test with the possession of or lack thereof of a boundaryless career attitude with a sample of secondary educators. The shift from traditional, organizational careers has grown tremendously over the last decade. Research has shown that professionals who adopt career models and attitudes that create increased career adaptability and mobility tend to experience greater measures of self-perceived career success. The boundaryless career model or mindset has been heralded as one of the most significant means to break organizational boundaries and experience greater measures of subjective career success. While this career model or mindset has been examined in many knowledge intensive sectors, it has infrequently been examined in the profession of education. With teaching having one of the highest turnover rates in the first five years of any profession, it is important to examine and analyze the construct of the boundaryless career and its subsequent effect on measures of subjective career success among a body of educators. This study examines correlations between measurements of subjective career success in groups of secondary educators in a southern state who have identified either as having or not having a boundaryless career model or mindset. This study examines the correlation between the two constructs when present and when not present, as well as the differences between the measures of the two groups. The study found when examining a group of 40 secondary educators that there was a significant difference in measures of subjective career success between the group that had the presence of a boundaryless career model or mindset and the group that did not. [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.]