This grounded theory study highlights the words of urban career teachers who participated on a wikispace (wiki). The purpose of the investigation was to offer urban career teachers a space, outside of their daily work, in which to recognize and understand their professionalism. The grounded theory content analysis is carried out by way of a study design informed by critical pedagogy. The questions explore how a wiki helps to illuminate: "who is a career teacher, what knowledge about career teachers is generated on a wiki, and what does this knowledge say about teachers who remain as career teachers?." Data was collected through the participant generated responses on the group wiki, documents, researcher's journal, and member-checks. The analysis of this data suggests that the urban career teachers participating in this study understood their professionalism by way of four major stakeholders. The intricacies of these stakeholders, including the inside of school relationships of students and colleagues, and the outside of school relationships of government and media are used as cues by urban career teachers as they navigate their professional role. The teacher-generated knowledge on the wiki is two-fold. First, the theory of Career TPS explains how the stakeholders of urban career teachers influence career teacher identity. Second, career teachers exhibit a navigational fluency that comes from experience and, at times, is challenged by the context in which a career teacher works. In response to these findings, the researcher offers some suggestions for future actions by administrators and policymakers, which reflect the complex nature of teacher identity, including actions which support the push and pull "of" and "by" stakeholders that career teachers learn to delicately balance everyday. Ultimately, the researcher determines that a more united approach for career teachers, one in which they can navigate their working context, including all stakeholders involved, will lead to stronger career teacher identity and positively influence the teacher retention crisis. [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.]