Dr. Bailey attended medical school at the University of Minnesota, and ophthalmology residency and neuro-ophthalmology fellowship at the University of Iowa. During residency, she won the PJ Leinfelder Award for the best research project, identifying a novel autoimmune retinal disease. She has published other articles, including in the Journal of the American Medical Association in 2018. She served as Chief of Ophthalmology at Ehrling-Bergquist U.S. Air Force Hospital before transitioning to private practice and later academic practice. She initiated an amblyopia screening program in the Air Force, earning a Commendation Medal, and later founded and led a non-profit for amblyopia screening in the community, as well as a diabetes photographic screening program at Methodist Hospital in Omaha. She was given the Milagro Award from One World for volunteering to perform cataract surgery and donate other free eye care for indigent patients over a 12-year period. At the University of Iowa in 2018, she was the site Principal Investigator for a surgical intracranial hypertension NIH-funded multicenter trial, and served as Director of the Perimetry Service. She is currently the Chair of the American Board of Ophthalmology. In 2021, she received the North American Neuro-ophthalmology Society Women in Neuro-ophthalmology Leadership Award and attended the Harvard Career Advancement and Leadership Skills for Women in Healthcare conference.