This autoethnographic narrative explores the challenges and successes of employing critical pedagogy in an eighth-grade history classroom. Using the threads of teacher, scholar, and individual, the author shares the intellectual and emotional progression through hope, frustration, humility, and growth that this endeavor demanded. Further, this work demonstrates that while each educator's implementation of critical pedagogy is necessarily unique, the process of personal and professional development that occurs when sincerely seeking to establish a critical and equitable classroom has the potential to significantly benefit not only students but teachers as well.