There are a lot of different reasons why Jesus would speak in "figures" as he calls them. One is the mysterious plan of the Father, which could include God's knowledge of who would accept him, and why. In various ways, Jesus has taught them about not wasting their breath, or throwing pearls before swine, as it says in another place.
Using metaphors also keeps the enemies of Jesus off-balance just a bit, until it is time for the Cross and Jerusalem. But now among his most intimate friends, Jesus makes everything clear. The things he says are not new; he has said that he is going to the Father before, but they didn't understand. Maybe St. John's purpose in this passage is to tell us that this is the moment when they understood what Jesus was saying.
Jesus says that they're going to be scattered, and that they will have trial and tribulation. He tells them that they will abandon him, but that he will rely on his relationship with the Father.
Jesus tells them and us to be of good cheer, which again doesn't sound like something we can just do on our own, but we can ask Jesus to help us. He told the disciples that he had often spoken to the Father on their behalf, but now they can ask Jesus on their own behalf, because they will have a close relationship to the Father because of their friendship with Jesus.
When Jesus says he has overcome the world, it's a stronger statement than it first appears. If we understand "world" as everything opposed to the will of God, Jesus is saying that he has overcome all evil. This is the power of his life, and His atoning death for us.
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