Background: Career choice satisfaction among plastic surgeons has a significant effect on the quality of patient care and workforce shortages. This study investigated career choice satisfaction among Saudi plastic surgeons to identify associated factors. Method: A cross-sectional study was conducted via an online self-administered questionnaire sent in April 2021 to all Saudi plastic surgeons. The questionnaire was composed of 23 items in four domains: demographics, plastic surgery training, current practice workload, and job satisfaction. The analysis was performed at a 95% confidence interval using the Statistical Package for Social Sciences, version 23.0 (IBM, Armonk, N.Y.). Results: A total of 63 plastic surgeons were included in this study (82.5% men; 17.5% women), with an overall response rate of 76.8%. The leading cause of job dissatisfaction for women was financial remuneration (28.8%) ( P = 0.008). The main factor for men was work–life balance (38.5%) ( P = 0.028). Of the different backgrounds, the highest satisfaction was among those with a background in German residency programs, and the lowest was among those with French residency programs ( P = 0.045). Surgeons from the southern region had a higher satisfaction rate than those from other regions; those from the central region had the lowest rate ( P < 0.001). Conclusions: Our survey-based study found that Saudi plastic surgeons with German residency training, practicing in the southern region or who exceeded 11–20 years post-training had the highest job satisfaction. As such, surgeons’ job satisfaction can be improved by ensuring work–life balance.