Twenty-first century learners in post-secondary educational environments find themselves involved in online learning. Acquiring graduate degrees, especially for working professionals, has precipitated the need for effective, rigorous, relevant, and timely coursework online. Utilizing the qualitative research method of auto-ethnographic reporting, we explored one individual's experience acquiring an online doctor of education degree from a research university in the state of Texas. The results indicated three major components: (1) personal: including but not limited to family, work, and cultural responsibilities; (2) coursework: including but not limited to rigor, relevance, requirements, collaboration, and personal contact with instructors; (3) writing of the record of study (ROS): including but not limited to the selection of the dissertation committee, formulation of the research topic, approval of topic, researching, writing, defending, and submitting the ROS. The implications on future program development are discussed, as well as an exploration of normative boundaries associated with online learning.