The purpose of this study was to explore the experiences and motivational factors that influenced educational and career decisions of United States military veterans who transitioned out of the military and into an information technology (IT)-related career field. The study investigated the reasons veterans decided to pursue IT-related careers, the reasons they selected their educational programs to gain entry into the field, how they described their experiences within those programs, and how satisfied they have been during the entry-level phase of their career. Veterans who served in IT-related career fields during their time in the military were not included in this study. This case study presents the perspectives of 12 veterans who successfully transitioned out of the military, completed one of several educational pathways, and attained their goal of working in an IT-related career field. Several findings emerged as a result. Veterans who participated in this study were satisfied with their decisions to pursue careers in the IT workforce. They approached career transitions from different situations, and those situations influenced the decisions they made and pathways they pursued to find success. The participants based their decisions to pursue their overarching goal of working in an IT-related career on internal or value-based motivations; however, when selecting an educational pathway to attain that goal, they deliberately considered the practicality of their circumstances. In addition, participants attributed part of their success to personal motivations, helpful strategies, and external support. Ultimately, future transitioning veterans can learn several lessons from these findings regarding career assessment and counseling, considerations for pathway selection, and elements of success. [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.]