Jesus does not end things the way we might expect. After talking about detachment from parents (fine), and then the need to plan things out in advance (reasonable), He finishes by saying “In the same way, every one of you who does not renounce all his possessions cannot be my disciple” (Lk. 14:33). One of these things is not like the others. Planning ahead and having right relations that do not compromise discipleship have little to do with owning and possessing. At least, not on the surface.
The reality is that the things we own (or think we own) are our greatest weak spots. If a general surveying his fortress is looking for weak spots in the walls and defenses, a Christian is surveying his soul is looking for places where he is possessive. The things that we think we deserve and that no one—not even God—can take away from us are often our greatest weaknesses. If I say “this is mine, and you have no right to tell me otherwise!” I am setting up a sphere where not even God may enter. This is true whether it is something we own, a relationship, or anything else. And once there is an area we think God has no place, it is a very inviting weak spot for the Enemy of human nature to exploit.
With this in mind, we ought to consider what we think we own and what we treat as a gift. To the extent we say “this is mine, to do with as I please”, we are vulnerable to attack. To the extent we say “this is from God, to do with as He asks,” we may repel the assaults of all who wish to destroy us.