INTRODUCTION: Dental students' satisfaction with their own career can significantly improve the quality of care provided to patients. The aim of the current study was to assess the level of career satisfaction amongst Saudi dental students and dentists. MATERIALS AND METHODS: A cross-sectional survey was conducted from October 2019 to January 2020 all over Saudi Arabia. A sample of 750 Saudi dental students and dentists were invited to complete an online questionnaire. The questionnaire was composed of two sections of closed-ended questions. The first section included personal, professional background factors and level of career satisfaction assessed. The second section included different reasons for choosing dentistry as a career. Multivariable linear regression was used at significance <0.05. RESULTS: Only 674 responded to the questionnaire. About half of the included respondents were males. Most of the participants were undergraduate students attended Saudi dental schools. 72.3% chose dentistry for helping other people. Graduated dentists had significantly lower satisfaction score than dental students (p = .007). Dentists, who chose dentistry because it is a secured job with good income (p < .001), had significantly lower satisfaction score than those who did not, whilst those who chose it for the social status had significantly higher satisfaction score than those who did not (p = .04). CONCLUSION: Dental students and dentists were motivated to choose dentistry as it is an opportunity to help others and achieve good salary with appropriate social position in community. Dental students were more satisfied than dentists due to lack of financial responsibilities and absence of educational expenses.