Physician well-being remains a critical topic with limited information concerning the impact of the progression of training and duty hours. To date, our knowledge and interventions have not adequately addressed these issues. We assessed differences in well-being across the USA: (1) between all post-graduate trainees and their academic core faculty; (2) between all obstetrics and gynecology trainees and their academic core faculty and (3) during the progression of training within obstetrics and gynecology (OB/GYN). A cross-sectional study analyzing responses to well-being questions included in the 2017-2018 Accreditation Council for Graduate Medical Education (ACGME) surveys given to all U.S. trainees and core faculty. More than 85% of all U.S. physician-trainees and faculty surveyed responded. Respondents included 128,443 trainees from all specialties combined, 5,206 OB/GYN residents and 799 OB/GYN subspecialty fellows. A total of 94,557 faculty from all specialties combined, 4,082 general OB/GYN faculty and 1,432 sub-specialty OB/GYN faculty responded. Trainees were more negative than faculty for the majority of questions for both all trainees combined and within OB/GYN when progressing from resident to subspecialty fellow to subspecialty faculty (p ≤ 0.05). Questions focusing on work satisfaction (e.g., pride in work) were more negative for residents compared to fellows and for fellows compared to faculty. In contrast to work satisfaction, responses to the question ‘Felt the amount of work you were expected to complete in a day was reasonable’ showed either no difference or higher scores for trainees compared to their faculty. Although an issue for all physicians, well-being impacts trainees more, and differently, than faculty and well-being improves during training from resident to fellow to faculty. Survey responses suggest that interventions should focus on workplace satisfaction over workplace environment areas and further limitations in duty hours are unlikely to improve physician well-being.