14:31-32 This second parable makes essentially the same point as the first one. However the cost of failure in this one is not just embarrassment but personal destruction. It is very important to assess the strength of one's enemy correctly. Jesus was not encouraging people to stop following Him because they feared they could not withstand temptations. He wanted them to follow Him, but intelligently, not naively. There were probably no kings in Jesus' audience, but the people could easily put themselves in the place of a king.
"Discipleship to Jesus Christ is not an invitation to a Sunday school picnic. It is an invitation to spiritual warfare."342
14:33 Jesus now applied the parables (cf. vv. 26-27). Obviously the Twelve had not given away everything they owned. They had adopted a lifestyle conducive to fulfilling their mission that involved relatively few possessions. Therefore we should probably understand Jesus' command as requiring a willingness to part with possessions as necessary to follow Jesus faithfully (cf. 12:33). Elsewhere Jesus taught His disciples to manage the possessions that they did have wisely (16:1-12). A person should not begin a venture without sufficient resources to finish it. Similarly one should not begin following Jesus without being willing to sacrifice anything to complete that project successfully.