Our youngest son recently graduated from high school with plans to attend college in the fall. Because of a number of vacations and other summer plans, it hasn’t worked out for him to get steady employment during the time between graduation and college departure. As such, he’s kind of broke most of the time, but he has things he wants to do, some of which cost money. I will periodically get a text message saying, “Dad, could you loan me some money for [insert item here]?” When I get such texts, I usually have two competing thoughts. The first is I love my son and want to do everything I can for him. I want him to be comfortable and enjoy life. Just give him the money! The second thought is Hold on! He needs to learn to be responsible and that money doesn’t grow on trees. Make him work for it. Those thoughts duke it out in my brain for a moment, and then after consultation with my amazing wife, we usually arrive at a compromise that enables generosity combined with responsibility.