<p>This synthesis will explore the premise of a working outreach platform comprised of experiential methodology, and practical tools and strategies to serve the intended audience. The paper presents an in-depth example of a workshop curriculum created for middle-school aged youth, (12-14 years old), who may struggle with self-esteem, understanding their self-worth, and making responsible decisions. The work explores two intersecting ideas that 1) poor self-concepts and misperceived thinking can lead youth to behave negatively and make detrimental decisions, and 2) theater involvement can produce a theater-based skillset capable of combating those poor self-concepts and misperceived thoughts and changing the trajectory of youths’ lives. Lastly, research findings of other comparable youth programming, theories, and self-improvement workshops with commonalities and shared objectives are presented to explore tensions between various theories, ideas, and workshop activities. The three guiding questions used as a focal point and to drive the direction of the paper are 1) How does or how can theater skills apply to real life? 2) How can theater performing arts teach youth or help youth develop? 3) How does theater performing arts help youth become more productive or successful. I employ personal reflections as a case-study for this project, drawing upon my various life-stage roles from adolescence through professional middle school educator to dedicated reflective practitioner utilizing those experiences, along with outside sources, to support the perspectives and rationale laid forth throughout this paper.</p>