Background Medical educators face many challenges, including the absence of defined roles, lack of standard career paths, and limited support in systems that generally prioritize research and clinical productivity over educational activities. Providers also teach to widely varying degrees. This study was designed to specifically examine the professional rewards and obstacles experienced by physicians who have dedicated significant energy and career focus to medical education. Methodology A phenomenological approach was used in this qualitative study.Purposeful sampling was utilized to identify medical educators from different institutions and geographical areas. Participants were categorized by gender and career stage. Semi-structured interviews were conducted, and reflexive thematic analysis was used to develop themes across items and participants. Results Twenty-two medical educators were interviewed (11 males, 11 females), with an average age of 51 (range: 38-72) years. The average time from completion of training was 18 years (range: <1 to 41 years). Two main themes were constructed, which related to medical educators' career motivations and challenges: (1) Joy and purpose (subthemes: Interaction with learners, Impact, and Innovation) and (2) Everyone teaches(subthemes: Lack of recognition, Lack of reward, Malalignment of metrics) Conclusions The greatest source of motivation and satisfaction for medical educators is linked to the work itself; in addition to interactions with learners, educators derive pleasure from the innovation, collaboration, and systems thinking involved in their work. Importantly, participants also experience dissatisfaction, primarily due to a lack of recognition and reward, and metrics that do not consistently demonstrate their achievements.Participants provided examples of metrics that more accurately reflected the work of education; they identified clear benefits of academic promotion; and they highlighted significant challenges in the promotional system. The implementation of appropriate systems of measurement and reward is needed to better support the work of medical educators. Our aim should benot only to increase opportunities for satisfaction but also to reduce factors that cause frustration and limit advancement.