Much of the current literature on teacher retention centers around early-career teachers, with far less addressing mid-career teacher attrition. This research study explores the positive and negative experiences of five mid-career teachers, Toni, Sean, Susan, Debbie, and Jacqueline, explicitly focusing on the experiences that influenced their decisions to remain teaching. The participants were Teacher Leadership Academy alumni, a professional learning community in two separate Professional Development School programs. I used a qualitative case-study approach to examine the teachers' experiences and Identity Theory as a lens through which to view the findings. Semi-structured interviews and participant-constructed timelines were the primary sources used to elicit discussions about experiences participants identified as critically influential in their decisions to remain teaching. The findings indicate that mid-career teachers identify as learners and seek professional advancement opportunities that will allow them to continue growing as a professional but remain in the classroom. Additionally, differentiated support networks that provided participants with the types of support they each needed at different times in their careers also proved to be critical factors that kept participants teaching. Lastly, the findings showed that participants had opportunities to re-envision what it looks like to be a teacher and re-identify as teacher leaders by assuming and having the support to enact various leadership roles. The paper concludes by offering recommendations to stakeholders on best supporting mid-career teachers, as found through the study's findings. [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.]