In this autobiographical analysis of internalized guilt and social responsibility, I question why I choose to work in a helping profession. Why did I choose not to pursue a career as a visual artist? How are the two choices interrelated and/or exclusive of one another? I question whether my need to take care of others is in balance with my need to take care of myself. I feel as though my career goals originate more from guilt than a genuine desire to help others. How should compassion and empathy factor in the continuum between altruism and guilt? If so, where on this continuum does my motivation lie? I conclude by coming to appreciate what Anzaldúa writes in “Now let us shift…” (2002) that a “new paradigm must come from outside as well as within the system.” I will try to combine the creativity of my artist self with the powers vested in my teacher self to affect change in our social system. Perhaps my career will resemble the work of the “nepantlas [who] know their work lies in positioning themselves—exposed and raw—in the crack between these worlds, and in revealing current categories as unworkable” (Anzaldúa 2002). Or perhaps it will resemble the career of Morrie Schwartz the “Teacher to the Last” (Albom 1997).