When deciding to earn a doctoral-level degree, the stakes are high. It is a major investment in time, effort, and money. The stories in this collaboration present a down-to-earth representation of life on the doctoral journey. The authors are leading practitioners and researchers in their respective fields of social work and education, yet the outliers are applicable to any discipline. Each author has shared a part of their heart to give the reader keen insight into the life of a doctoral learner and, more specifically, a black woman on the journey. The stories deliver a unique form of transparency, encouragement, and support with one common theme: You can earn a doctoral degree despite marginalization, disability, or the heartbreaking challenges life may bring your way.