I love this idea. Give him a slew of envelopes, each one with a specific condition. Examples are: Open when you are feeling sick. Open when you need motivation. Open when work is aggravating you. Open when you need to remember how much I love you.
I like the idea for doing it for a child starting a new school or going off to college! Even though it was pinned as a one year wedding gift, I'm thinking of doing it for my daughter as she enters junior high in a couple of weeks. The Paper Gift for 1