Research on the future workforce in academic dentistry and oral surgery showed that a lack of dental educators can be expected. This study explored which factors affect oral surgery residents' decision-making process concerning choosing a career as an educator versus private practitioner. Specifically, this study investigates how three groups of factors, namely background characteristics (gender, race, marital status), level of engagement in different professional activities such as types of surgeries conducted and preferred, and professional values affect whether residents intend to go into private practice versus academic careers. A population study of the residents in oral maxillofacial residency programs in the US was conducted. In the first week of October 2010, recruitment emails were sent to all 535 residents in these oral surgery residency programs. A total of 51 emails could not be delivered. In response to the 484 delivered emails, 271 residents (response rate = 56%) responded to a web based survey. This survey consisted of questions concerning the residents' background characteristics, their career decision-making considerations, professional activities and values, and their job satisfaction. The data were analyzed with SPSS. While 65% of the respondents indicated that they intended to have a career in private practice, 35% intended or considered becoming academicians. The responses of the future private practitioners were compared with the responses of the residents who intended/considered to become educators. χ2 analyses were used to compare the responses to the categorical variables and independent sample t tests were conducted to test whether the average responses of the 2 groups were different. The results showed that there were significant differences in the background characteristics of the 2 groups: residents who considered academia as their future profession were more likely to be female (% female of educators: 29% vs % female practitioners: 8%; P < .001), were more likely to be non white (37% vs 20%; P = .006), were less likely to be married (43% vs 71%; P < .001) and had on average fewer children (0.33 vs 0.84; P < .001). No significant differences between these 2 groups were found in the way they financed their education, in the level of accumulated debt, and in their involvement in research both in dental school and during their residency program. However, there were significant differences in their involvement in different surgical activities and their preferences for different types of surgeries. While future educators spent a lower percentage of their time on dentoalveolar surgeries (45% vs 67%; P < .001) and significantly more time on surgeries related to trauma (18% vs 12%; P < .001), orthognathic surgery (17% vs 12%; P < .001), and craniofacial surgeries (9% vs 6%; P = .024) than future clinicians. These rates of engagement in different types of surgeries paralleled the level of enjoyment that these 2 groups of respondents reported for these professional activities. In addition, the 2 groups also differed in their professional values with future clinicians valuing having manageable hours, less time in the operating room and more time without patients more than future educators. In conclusion, understanding how residents who plan to become private practitioners differ in their background characteristics, professional activities, and values from residents who consider becoming dental educators might contribute to developing measures to increase the number of academics in oral maxillofacial surgery departments and thus avoid the shortage of educators in this field in the future.