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This paper is an autoethnography that chronicles my own pathway through our national system of public education from pre-secondary school experiences to my current status as an educational practitioner, leader, and doctoral student. The work allows me to personally and publicly reflect on my path toward critical consciousness through an investigation of the multiple layers of social conditioning specific to the high poverty, minority-majority settings I experienced. I analyze my metamorphosis, from a high achieving student to a detached resister of Western social norms, as I entered and dropped out of one of Chicagoland’s notoriously under-performing school districts. These autoethnographic accounts demonstrate the rich diversity of qualitative research methodology, especially as they pertain to authentic leadership and praxis.