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To understand the professional aspirations of oral and maxillofacial radiologists (OMRs) by exploring their career choices and their association with educational background, engagement in professional activities, professional values, and overall level of career satisfaction. This prospective cross‐sectional study surveyed board‐certified OMRs in the United States and Canada from September to December 2019. A web‐based questionnaire was created comprising 37 multiple‐choice questions and an open‐ended question focusing on their opinions regarding the profession's future. A thematic approach qualitatively explored open questions. Of the 86 OMRs, 68, 10, and eight were board certified in the United States, Canada, and both countries, respectively. Activities considered "rewarding" included teaching and mentoring (65%) and radiologic reporting (55%). The majority spent approximately 20–30 h/week writing radiographic reports and less than 10 h in research. On an average, OMRs produced 21.9 (SD 12.8) reports per day. Activities considered less rewarding included administrative work (11%) and productivity pressure in institutions. OMRs working in academia reported higher incomes (p< 0.05). Finally, the majority of the OMRs were pleased with their career choices (79%). There is an association between the contemporary OMRs' satisfaction feeling, teaching/mentoring, and the future challenges of participating in multidisciplinary teams. Overall, diverse career choices lead OMRs to be proud of their profession and significantly satisfied.