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Once again, it is difficult for those of us who know how the story ends to appreciate the disciples' confusion over what was about to occur. They were full of sorrow (16:6, 20) when they should have been rejoicing, believing that Jesus was going to His Father (John 14:28), and trusting that they would soon see Him again as He promised. Moreover, Jesus told them it was to their advantage that He go; otherwise the Holy Spirit would not come to them (16:7). His encouraging words apparently had little effect on their disposition, yet He was still certain that their sorrow would be turned to joy (16:20, 22). God is in the business of giving "beauty for ashes, the oil of joy for mourning, [and] the garment of praise for the spirit of heaviness" (Is. 61:3). How often we are like the eleven, weeping when we should be dancing!
Jesus promised that when the Holy Spirit came, He would "convict the world" of three things, "sin and righteousness and judgment" (16:8). Has the Holy Spirit been doing those things or not? I believe He has, which makes Him the greatest evangelist on our planet. Because of the conviction of the Holy Spirit, everyone in the world innately knows they are sinners who are called to live righteously and who will one day stand judgment before God. Of course, people deceive themselves in this matter, filling their minds with lies that suppress the truth in their hearts, but they will have no excuse before God. We are wise to pray for God to lead us to those who are yielding to rather than resisting the Spirit's conviction.
The coming Holy Spirit's ministry would not be limited to convicting the world of certain essential truths, but also of guiding the church into truth (16:13), which begs the question, "Why then is the church so divided regarding doctrine?" The answer is that much of the "church" is not the true church of Christ, but rather an unholy religious conglomeration of unregenerate leaders and followers, the "blind leading the blind." Second, God does not override the free wills of His children, and He does not force them to believe truth or to stop listening to those who twist Scripture to their own liking. Thus, even true believers can be deceived. And third, much of the doctrinal differences between genuine believers revolve around non-essentials. They agree, however, on the essentials.
Jesus' promise to His disciples, "Truly, truly, I say to you, if you ask the Father for anything in My name, He will give it to you" (16:23), was not, as it is sometimes taken, a blank check that we can use to acquire material luxuries from God. Note that Jesus' made this promise within the context of the disciples' confusion about God's plan, and His promise of the Holy Spirit's leading them into truth.
Note also that the sentence directly before His promise in 16:23 reads, "In that day you will not question Me about anything." Then He said, "If you ask the Father for anything in My name, He will give it to you" (16:23). Jesus was encouraging the eleven to ask for understanding and insight. It is within that context that He promised in His very next sentence, "Until now you have asked for nothing in My name; ask and you will receive, so that your joy may be made full" (16:24). Again, He was not implying that they should ask for material luxuries to make them happier, but to ask for understanding, so that their current sorrow could be turned into joy. This blessing is not limited to 11 disciples who lived 2,000 years ago. It is the privilege of all believers today as well. James wrote:
If any of you lacks wisdom, let him ask of God, who gives to all men generously and without reproach, and it will be given to him. But let him ask in faith without any doubting (Jas. 1:5-6).
May we be unlike the eleven in this regard, who apparently didn't take advantage of Jesus' wonderful promise that would have filled them with joy in the midst of their sorrow!