Fear of failure starts early in life, and is common among high achievers. From their earliest years, many gifted children are successful in almost everything they try because they are under challenged, and paradoxically, become failure-avoidant. When parents always encourage their children to get the highest grade or to be "the best," they may be discouraging them from seeking challenges that are optimal for their level of possible accomplishment. Adults in their lives also need to take risks and to model a growth mindset prepared to cope with all possible outcomes. This article presents the following topics in teaching children to fail: (1) Embrace Mistakes; (2) Manage Time; (3) Absorb Disappointment & Modeling Behavior; (4) Develop Islands of Competence; (5) Separate Failure from the Child; and (6) Share and Care.