Introduction: Dentists career satisfaction can significantly affect their quality of life and the quality of healthcare services provided to their patients. The aim of this 10-year repeated cross-sectional study is to assess career satisfaction among dentists and investigate its influencing factors. Methods: Participants were distinct cohorts of dentists (n = 115) who graduated from King Abdulaziz University, Jeddah, in 2013, surveyed at 2 time points: upon graduation and 10 years later (2023). Data were collected through anonymous self-administered questionnaires. Descriptive statistics and bivariate analyses were performed, with the significance level set at <0.05. The distinct cohorts allowed for population-level insights but introduced variability that may affect longitudinal comparability. Results: The study included distinct cohorts of 90 respondents at each survey period (response rate was 78.3%). Of these, 68.9% were satisfied with their careers. Those who were satisfied were more likely to have a higher GPA (P value = .002), have a postgraduate degree (P value = .002), and practice in an academic institute (P value < .001). Only 31.1% felt their current career status was very aligned with their expectations set 10 years ago. (56.5%) were either considering changing their career away from dentistry or still unsure. Although 58.9% were working as full-time dentists, 45.6% of them are not planning to continue as they have the desire for early retirement. In fact, 7.8% have already quit dentistry and shifted to other professions. Only 15.6% chose dentistry because they were passionate about it. (52.2%) are planning to start a new full-time career outside dentistry. Conclusions: GPA, higher education, and work institutions influenced satisfaction and career alignments. Unsatisfied dentists are interested in establishing new careers in other fields consistent with Saudi Vision 2030. Clinical relevance: Investigation of students' motivation by academic advisors is encouraged to guide them to achieve their expected goals and, thus, career satisfaction. (c) 2024 The Authors. Published by Elsevier Inc. on behalf of FDI World Dental Federation. (http://creativecommons.org/licenses/by-nc-nd/4.0/)