One issue that often weighs on me heavily is the catechesis for and administration of the sacraments of initiation for those who don't seem committed to their faith. This is especially difficult in the case of children of parents who don't give much visible evidence of faith. Situations can be very hard. Sometimes a grandparent pushes for the baptism of a child, but the parents readily admit their indifference. Sometimes a kid admits that she doesn't care about being confirmed, and a conflict between the parents and the catechists and clergy erupts. Sometimes people bring babies here from far away because this is their ancestral parish. When I ask what their parish is where they actually live, sometimes they don't even know. When I suggest that this is their opportunity to join the parish where they now live, get involved, and baptize their child there, a big fight typically ensues. These are ones that keep me up at night.
So it really made my day today to see that Pope Benedict had spoken a little bit on the question, albeit informally. Check out his beautiful remarks here.