Empowering youth through the exploration of their possible futures is a fresh and innovative approach to the Teaching Personal and Social Responsibility Model (TPSR). The purpose of this study was to examine the combination of TPSR with the theory of possible selves. This combination, called the “Career Club,” was a program specifically designed to better assist students in understanding and facilitating their future decisions. It was an extension of the alternative after school TPSR program structure called, the “Coaching Club.” The Career Club was held for 90 minutes each week for nine sessions at an inner city elementary school in a large metropolitan city. Participants were comprised of 12 seventh and eighth grade boys and girls with one to five years of experience in a TPSR program. Assuming that participants were already familiar with TPSR's original concept of “coaching” as a form of empowerment and leadership, the Career Club applied these skills as a platform from which to approach possible futures in a self-selective and self-aware manner. The participants were offered the opportunity to coach a group of fourth graders intended to provide both a real-world example of a career, and the opportunity to contemplate other possible futures. The Career Club was based on the rationale that youth in TPSR programs often do not transition well to the work world, college, or other aspirations they initially held. Two phases were developed, progressing from coaching-as-a-possible-future to individual-future-choices. Phase I involved the dynamics of coaching opportunities for awareness, self-evaluation, and goal-setting; phase II involved a transference in which they could hopefully become aware, self-evaluate, and goal-set in their own career exploration. The goal of these nine sessions was to successfully implement the program; observe and record participant progress, questions, and concerns; and analyze the potential impact of the program. Data sources included document analysis, lesson observations, interviews with participants and assistant instructors, and field notes. Themes were classified into the following categories: coaching as a necessary component, coming to understand possible futures, and “hoped-for-selves” and “feared-selves”. The data suggested Career Club was effective in providing the participants with a meaningful career exploration in coaching. Data also suggested the linking of these coaching experiences to elements necessary for the realization of their choices for future orientation.