Professional identity development encompasses concepts of personal identity and self-efficacy while continued education supports a teacher's change in perspective and practices leading to professional growth. A combination of motivation and personal goals guide teachers' behaviors as they interact within their social and cultural environments. The purpose of this multiple case study was to understand how kindergarten teachers perceive interactions in social, organizational, and academic environments to gain personal perspectives of barriers and supports that influence a decision to pursue or not pursue an advanced degree in education as well as their ideologies about continued formal education. With limited research specific to kindergarten teachers and professional development or their interest in graduate degree obtainment, the need to identify perceived barriers or supports kindergarten teachers have about pursuing an advanced degree was identified. The need to raise awareness of practices that tend to marginalize this population of educators was an additional focus of the study. Six kindergarten teachers participated in semi-structured interviews and written communications that reflectively provided insights about their choice of obtaining or not obtaining an advanced degree. All participants found time and money most concerning to continue their professional growth and development in an advanced degree program, but it was intrinsic motivation from participants who had advanced degrees that helped them overcome perceived barriers in their quest to obtain an advanced degree. Results suggest that dialogue with others in and outside of the workplace and in the academic environment provided interest and engagement in learning when topics were relevant and applicable to the kindergarten teachers' professional positions. [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.]