Damon spent his life doing the things he cared about with the people he cared about, he always had his priorities in order, and he helped the people around him realize what their priorities should be. That is true greatness, in my book.
Failure just happens to be an unavoidable byproduct of action. Failure also happens to be the best teacher we have, you just have to give her a chance and be willing to learn!
I think the goal should be to prepare the ones you love. Otherwise, you just have a sheltered child and an imminent disaster. They need a ready defense for the world and the pain it brings. They need faith and hope and love.