In the quest to get the best from those for whom they are responsible, some parents and managers seek or demand perfection. But do such expectations benefit the targets, in terms of their capacity for creativity? The present research examines how perfectionistic parental and supervisor expectations influence employees’ fear of failure and creativity; in particular, the authors propose that perfectionistic parental expectations promote a fear of failure, which undermines employee creativity later in life. In line with social cognitive theory, when perfectionistic supervisor expectations repeat and reinforce these early life experiences, the negative mechanism may be strengthened. Tests of the hypotheses rely on two time-lagged field studies in different cultures (214 U.S. employees, 276 supervisor–employee–parent triads from a Chinese organization) and show that the indirect effect of parents’ perfectionistic expectations on creativity, through fear of failure, is stronger when perfectionistic supervisor expectations are high. This study thus offers unique insights into how familial and work experiences can jointly affect a person’s fear of failure and further creativity at work.