This qualitative multiple case study focused on National Board Certified teachers from Generation X who have left the classroom. The study explored aspects of the teaching profession, the National Board Certification process, and Generation X as potential influences for National Board Certified teachers from Generation X to leave the classroom. The study provides a detailed description of six National Board Certified teachers from Generation X who left the classroom and two National Board Certified teachers from Generation X who have stayed in the classroom. Participant narratives describe choosing teaching, early career, pursuit of National Board Certification, and deciding to leave. Cross case analyses are provided within those who stayed, within those who left, and across groups. The study found that characteristics of the teaching profession that influence National Board Certified teachers from Generation X to leave the classroom include: perception of the profession, lack of performance differentiation, positive early career, unfair responsibility and lack of support, and salary. The study also found that no characteristics of the National Board Certification process influence certified teachers from Generation X to leave the classroom. Five of six leavers did not expect their careers to change after pursuing and earning National Board Certification. Most participants sought certification because they believed it provided professional validation. Finally, the study found that characteristics of Generation X that influence certified teachers to leave the classroom include: definition of career, desire to maximize earning potential, importance of work/life balance, need for challenge, and the aspiration to affect impact beyond the classroom. [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/en-US/products/dissertations/individuals.shtml.]