This study explores the impact of attending optional professional learning events on the critical consciousness development of Ready to Learn (RtL) mentors over the course of one program year. Ready to Learn is an out of school time math tutoring and mentoring program that seeks to address opportunity gaps in math learning for middle school students in a mid-size, Midwest urban public school. The program aims to achieve this by deploying highly trained mentors to provide social justice centered math learning experiences. One aspect of the training process for RtL mentors is attending optional events hosted by CUE or that feature CUE faculty members to deepen the mentors' knowledge of current and historical conditions that impact urban education. Critical consciousness, or "conscientizacao", developed by Paulo Freire, is the theoretical framework informing the study. A qualitative evaluation using hybrid thematic analysis was conducted to evaluate this professional learning strategy to identify best practices and future applications for lecture style events hosted by the Center for Urban Education (CUE) as professional learning for community educators working in out-of-school environments. Critical consciousness development in educators is essential in building awareness of inequity and injustice in both education and the broader society. The findings provide evidence that attending optional professional learning events offered by CUE support foundational critical consciousness development for mentors who choose to participate. Additionally, mentors demonstrated recognition of patterns of neoliberal influences on education in their post-event reflection responses and semi-structured interview responses suggesting a level of awareness that may lead to critical motivation and action. Moreover, once a person "chooses to see" and actively investigates factors impacting barriers to equity and justice they cannot unsee them. Thus, recognition of systemic oppression will create a new lens for RtL mentors to view their world no matter what career path they intend to pursue after their time in the program. Implications for future practice within the RtL program include continuing to offer opportunities for RtL mentors to attend professional learning events offered by CUE as a component of their self-directed professional learning, as well as incorporating event attendance as required training component. [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.]