"For it is the role of the parent to express his concerns and then take three steps back. Not one, mind you, not two, but three. Or maybe four. (But by no means five.) Yes, a parent should share his hesitations and then take three or four steps back, so that the child can make a decision by herself—even when that decision may lead to disappointment."

That's from a great book that I recently read, A Gentleman in Moscow