Conscientiousness is typically seen as a positive or desired personality trait in the workplace, with the overall assumption being “the more, the better”. Drawing on the behavioral concordance model, we challenge this assumption, expecting that the highest level of positive affect and the lowest level of negative affect will correspond at the point where state and trait conscientiousness converge. Using an experience sampling study and an event reconstruction study, we show that deviations from one’s level of trait conscientiousness relate to variations in positive and negative affect, but not in a straightforward way. While wellbeing was lower when people behaved less conscientiously than they normally do, increases beyond one’s typical conscientiousness level were largely unrelated to wellbeing. Moreover, people high in trait conscientiousness suffered more from negative deviations from their trait level than people low in trait conscientiousness. As a whole, our findings suggest that the interplay of personality states and personality traits is complicated, with both the state level and deviations from the trait level being relevant to wellbeing—calling for an integrative approach to personality.