Objectives: The drop-out rate among residents across all medical specialties in the Netherlands approximates 12.7%. This implies a capacity loss in the medical workforce, a waste of educational resources and personal damage to individuals. The aim of our study was to investigate reasons for dropping out of residency and the relationship with medical work experience after medical school and prior to residency, which is common among Dutch graduates.Method: A questionnaire listing 28 reasons for drop-out was developed and tested. The questionnaire was sent in a nationwide survey to all residents who drop out between 1 September 2017 and 1 September 2019. The respondents were asked to indicate on a 5-point Likert scale, how they weighed reasons for drop-out. Factor analysis was applied to identify dominant factors. Results: The response rate was 39% (N=129; 99 females) representing all medical specialties. The factor structure of our measure showed 5 factors; high emotional job demands, lack of professional satisfaction, incompatible lifestyle, tensions in working relationships and disappointing career perspectives. Of the respondents 69 (54%) had prior clinical experience as a physician-not-in-training in the same medical specialty before residency. The factor “lack of professional satisfaction” weighed heavier for respondents without prior experience as a reason for drop-out.Conclusion: Of influence on dropping out of residency is the lack of a clear image of the responsibilities as a physician within the residency of choice, fuelled by limited prior experience after medical school and before residency. One third of dropouts confirmed that prior physician experience within the same specialty could have prevented dropping out or prevented choosing this specialty in the first place.