Structurally, chapter sixteen links back to the lack of joy among Jesus’ disciples at his suggested departure; recall chapter fifteen: 11 These things I have spoken to you, that my joy may be in you, and that your joy may be full.

Sorrow Will Turn into Joy

16 “A little while, and you will no longer see me, and again a little while, and you will see me.”  17 Then some of his disciples said to one another, “What does he mean by saying to us, ‘A little while, and you will no longer see me, and again a little while, and you will see me’; and ‘Because I am going to the Father’?”  18 They said, “What does he mean by this ‘a little while’? We do not know what he is talking about.”  19 Jesus knew that they wanted to ask him, so he said to them, “Are you discussing among yourselves what I meant when I said, ‘A little while, and you will no longer see me, and again a little while, and you will see me’?  20 Very truly, I tell you, you will weep and mourn, but the world will rejoice; you will have pain, but your pain will turn into joy.  21 When a woman is in labor, she has pain, because her hour has come. But when her child is born, she no longer remembers the anguish because of the joy of having brought a human being into the world.  22 So you have pain now; but I will see you again, and your hearts will rejoice, and no one will take your joy from you.  23 On that day you will ask nothing of me. † Very truly, I tell you, if you ask anything of the Father in my name, he will give it to you. †  24 Until now you have not asked for anything in my name. Ask and you will receive, so that your joy may be complete.

Jesus uses the very natural metaphor of childbirth to explain that pain is a natural part of labor, “But when her child is born, she no longer remembers the anguish because of the joy of having brought a human being into the world.   Jesus consoles his disciples, telling them their present pain is ensures future rejoicing. In fact, the purpose of Jesus’ teaching is that their “joy may be complete.”

       Jesus reminds his followers that he cannot physically continue to be present for his disciples, reminding them that his mission has been to bring them to understand spiritual presence.  His discourse links back into chapter fourteen: 25 “I have said these things to you while I am still with you.  26 But the Advocate, † the Holy Spirit, whom the Father will send in my name, will teach you everything, and remind you of all that I have said to you.  27 Peace I leave with you; my peace I give to you. I do not give to you as the world gives. Do not let your hearts be troubled, and do not let them be afraid. “ This teaching continues, fully elaborated as the work of the Spirit:

The Work of the Spirit

“I did not say these things to you from the beginning, because I was with you.  5 But now I am going to him who sent me; yet none of you asks me, ‘Where are you going?’  6 But because I have said these things to you, sorrow has filled your hearts.  7 Nevertheless I tell you the truth: it is to your advantage that I go away, for if I do not go away, the Advocate † will not come to you; but if I go, I will send him to you.  8 And when he comes, he will prove the world wrong about † sin and righteousness and judgment:  9 about sin, because they do not believe in me;  10 about righteousness, because I am going to the Father and you will see me no longer;  11 about judgment, because the ruler of this world has been condemned. 11      “I still have many things to say to you, but you cannot bear them now.  13 When the Spirit of truth comes, he will guide you into all the truth; for he will not speak on his own, but will speak whatever he hears, and he will declare to you the things that are to come.  14 He will glorify me, because he will take what is mine and declare it to you.  15 All that the Father has is mine. For this reason I said that he will take what is mine and declare it to you.

Jesus' preparing to be absent physically from his disciples causes sorrow, but he points out to them that “it is to your advantage that I go away.”  Why?  The Advocate, Holy Spirit, will prove the world wrong in its unbelief about Jesus and the righteousness revealed in the cross and wrong about the triumph of evil; Jesus is who he says he is, and his righteousness is the sacrifice of himself for his mission, and all this is directed for the ultimate victory of good over evil. The Spirit of Truth will guide believers into the full truth about the historic nature of Jesus (See Oxford Annotated Notes). One should note that Jesus reveals himself as sent from the Father and the Advocate also will be sent from the Father:

Jesus says he will send the Paraclete from the Father (v. 26), thus affirming both that the Paraclete is associated in a primary way with the Father and that the Son is involved in his historical mission (14:26; 16:7). Then Jesus refers to the Paraclete as the one who goes out from the Father (v. 26). The meaning of this line has been the source of enormous controversy right down to today. Many Western Christians would say the going out is another way of referring to the historical mission of the Paraclete. The Eastern church, on the other hand, sees this as referring to the eternal relations within the Godhead: this procession of the Spirit is not into history; it is the coming forth of the Spirit from the Father from all eternity. The Son is God begotten, the Spirit is God proceeding, and the Father is the one source of both.

The Father as the one ultimate source of all is true to the thought of this Gospel and the rest of Scripture, but it is doubtful that this verse is dealing in its primary sense with the eternal relations between the Father and the Spirit. The word used for from (para) does not denote source in this sense. Indeed, the line in the Nicene Creed referring to the eternal relations is "I believe in the Holy Spirit . . . who proceeds from (ek) the Father." The Greek fathers who refer to the eternal procession use ek and even change para to ek when referring to verse 26 in this connection (Westcott 1908:2:213). Furthermore, the language in our verse (para) is used elsewhere in John to describe Jesus' coming forth from the Father on his mission within history, though with a different verb (16:27; 17:8). Thus, the going out probably also refers to the historical mission of the Spirit. Jesus repeats the thought in this way to emphasize that the Spirit is from the Father--that is, like Jesus himself, he is not of this world.
http://bible.gospelcom.net

        L. Richards in Every Teaching of Jesus in the Bible explains Jesus' instructions to his disciples as threefold: the Spirit's ministry to the world, to the disciples, and to Jesus himself. The disciples learn that "when the Holy Spirit comes He--and they--will continue to present Jesus to the world. As a result they too will be persecuted, for 'the world has not know the Father nor me' (John 16.3)" Richards, L., Pegoda, D., & Gross, P. 2001. Every teaching of Jesus in the Bible. Includes index. T. Nelson: Nashville. The work of the Spirit to the world is one of convicting (establishing guilt and guaranteeing punishment) of sin, righteousness, and judgment.. And, as Richards points out, the ultimate sin is "a fixed refusal to accept God's Son." The role of the Spirit will be to guide the disciples into all truth not yet bearable. Richards says the wonderful promise Jesus gives in this chapter is that the Spirit will guide his disciples into the will of God and that living in truth will set them free. Thus, the Spirit "will serve as a conduit, communicating Jesus' leading." Finally, "as the Spirit communicates Jesus to the world and Christ's guidance to believers, Jesus is glorified."  Jesus completes his instruction by telling his disciples he is going to the Father (16). The Intervarsity Commentary on John summarizes Jesus' instructions as telling his disciples that they have already been transferred in the Kingdom of God, and this Kingdom is not of the world:

The disciples are included in the world's hatred of Jesus because, like him, they are not of this world (v. 19; cf. 8:23; Neyrey 1988). They are Jesus' friends (philoi, 15:14-15), and thus they are not loved (ephilei) by the world. Jesus has chosen them (exelexamen) and appointed that they to go bear fruit (15:16), and this commission was based on a more fundamental act that he now refers to as choosing them (exelexamen) out of the world. They have been transferred to Jesus' kingdom, which is not of this world (18:36). The world's hatred of them, therefore, is an encouragement to the disciples since it is due to the difference Jesus has made within them. This does not mean the world has no hatred for others besides Christians. Nor does it mean that someone who is hated by the world is necessarily being true to God. But Jesus does say that those who are his disciples are quite distinct from all that is in rebellion against God and should not be surprised when opposition arises.Jesus refers his disciples back to his saying, "No servant is greater than his master" (v. 20; cf. 13:16). Earlier Jesus was referring to his example of humility in washing their feet. Now this saying applies to his humility in undergoing persecution by the world, even to the point of death. Here we see the incredible humility of the master, who is Lord of all. If humility is appropriate for a slave, how much more for a slave of such a master. Jesus concentrates on two items of comparison in particular--persecution and obedience to his teaching. While Jesus' statement if they obeyed my teaching could refer to those who did in fact do so, the present context is focused on rejection (vv. 20, 21), so the idea is probably more like "they will follow your teaching as little as they have followed mine" (NEB). Thus, the disciples are rejected not only because they are not of this world, but also because they are proclaiming a message (cf. v. 27). The present text shows the disciples in the role of prophets, meeting the prophets' fate. As the Lord told Ezekiel, "The house of Israel is not willing to listen to you because they are not willing to listen to me, for the whole house of Israel is hardened and obstinate" (Ezek 3:7). There has been plenty of such hardness within the church as well.

Jesus summarizes his point thus far by saying, They will treat you this way because of my name (v. 21). His name refers to his identity and his character as it is made manifest (see comment on 1:12). But Jesus cannot be understood apart from the Father, so he concludes that the reason they reject him is their ignorance of the One who sent me. Here is the core problem (cf. 5:37-38; 7:28; 8:19, 47, 55), which introduces the main point of the rest of this section (vv. 22-25). Jesus has been speaking of the connection between the treatment he has experienced and that of his disciples. Now he focuses on his own ministry and its relation to the Father.

His central assertion is that this ignorance of the Father is culpable because of the witness he has borne in word and deed. He has spoken to them the words of the Father himself (14:10-11) and shown them the deeds of the Father (5:19, 30), deeds unlike anyone else's (v. 24). If he had not spoken and acted thus they would not be guilty of sin (vv. 22, 24). The text says literally, "they would not have sin" (hamartia). Hamartia can refer to guilt, but here the reference is more likely to sin itself. For in John's Gospel sin is understood as lack of faith in Jesus, that is, hatred of him and his Father (Michaels 1989:276). The opponents do not think they hate God, but such is the case given their hatred of Jesus (vv. 23-24). "This hatred is the human `no' to the divine `yes' expressed in the mission of his Son" (Ridderbos 1997:525).
http://bible.gospelcom.net

     In teaching his disciples, Jesus tells them that his purpose is to prevent them from stumbling. One recalls immediately that already in John 13,  Judas Iscariot has stumbled.  What will be the fate of Judas—heaven or hell?  The reader will recall that others of the disciples have doubted or been guilty of unbelief, or at least, not full belief.  In deciding Judas’ fate, it may be useful to put all the scriptural references in front of the reader; I am indebted to the following source for the following structure, and to some degree, for the explanation--http://www.tentmaker.org/Dew/Dew3/D3-JudasIscariot.html I have taken the liberty of adding high-lights for important themes:

Scriptures pertaining to Judas

John 13:21-31
21 After he had said this, Jesus was troubled in spirit and testified, "I tell you the truth, one of you is going to betray me."
22 His disciples stared at one another, at a loss to know which of them he meant.
23 One of them, the disciple whom Jesus loved, was reclining next to him.
24 Simon Peter motioned to this disciple and said, "Ask him which one he means."
25 Leaning back against Jesus, he asked him, "Lord, who is it?"
26 Jesus answered, "It is the one to whom I will give this piece of bread when I have dipped it in the dish." Then, dipping the piece of bread, he gave it to Judas Iscariot, son of Simon.
27 As soon as Judas took the bread, Satan entered into him. "What you are about to do, do quickly," Jesus told him,

28 but no one at the meal understood why Jesus said this to him.
29 Since Judas had charge of the money, some thought Jesus was telling him to buy what was needed for the Feast, or to give something to the poor.
30 As soon as Judas had taken the bread, he went out. And it was night.
31 When he was gone, Jesus said, "Now is the Son of Man glorified and God is glorified in him.

Matt 26:45-50
45 Then he returned to the disciples and said to them, "Are you still sleeping and resting? Look, the hour is near, and the Son of Man is betrayed into the hands of sinners.
46 Rise, let us go! Here comes my betrayer!"
47 While he was still speaking, Judas, one of the Twelve, arrived. With him was a large crowd armed with swords and clubs, sent from the chief priests and the elders of the people.
48 Now the betrayer had arranged a signal with them: "The one I kiss is the man; arrest him."
49 Going at once to Jesus, Judas said, "Greetings, Rabbi!" and kissed him.
50 Jesus replied, "Friend, do what you came for." Then the men stepped forward, seized Jesus and arrested him.

John 18:2-9
2 Now Judas, who betrayed him, knew the place, because Jesus had often met there with his disciples.
3 So Judas came to the grove, guiding a detachment of soldiers and some officials from the chief priests and Pharisees. They were carrying torches, lanterns and weapons.
4 Jesus, knowing all that was going to happen to him, went out and asked them, "Who is it you want?"
5 "Jesus of Nazareth," they replied. "I am he," Jesus said. (And Judas the traitor was standing there with them).
6 When Jesus said, "I am he," they drew back and fell to the ground.
7 Again he asked them, "Who is it you want?" And they said, "Jesus of Nazareth."
8 "I told you that I am he," Jesus answered. "If you are looking for me, then let these men go."
9 This happened so that the words he had spoken would be fulfilled: "I have not lost one of those you gave me."

Matt 27:3-10
3 When Judas, who had betrayed him, saw that Jesus was condemned, he was seized with remorse and returned the thirty silver coins to the chief priests and the elders.
4 "I have sinned," he said, "for I have betrayed innocent blood." "What is that to us?" they replied. "That's your responsibility."
5 So Judas threw the money into the temple and left. Then he went away and hanged himself.

6 The chief priests picked up the coins and said, "It is against the law to put this into the treasury, since it is blood money."
7 So they decided to use the money to buy the potter's field as a burial place for foreigners.
8 That is why it has been called the Field of Blood to this day.
9 Then what was spoken by Jeremiah the prophet was fulfilled: "They took the thirty silver coins, the price set on him by the people of Israel,
10 and they used them to buy the potter's field, as the Lord commanded me."

Acts 1:15-26
15 In those days Peter stood up among the believers (a group numbering about a hundred and twenty)
16 and said, "Brothers, the Scripture had to be fulfilled which the Holy Spirit spoke long ago through the mouth of David concerning Judas, who served as guide for those who arrested Jesus--
17 he was one of our number and shared in this ministry."
18 (With the reward he got for his wickedness, Judas bought a field; there he fell headlong, his body burst open and all his intestines spilled out.
19 Everyone in Jerusalem heard about this, so they called that field in their language Akeldama, that is, Field of Blood.)
20 "For," said Peter, "it is written in the book of Psalms, May his place be deserted; let there be no one to dwell in it,' and, May another take his place of leadership.'
21 Therefore it is necessary to choose one of the men who have been with us the whole time the Lord Jesus went in and out among us,
22 beginning from John's baptism to the time when Jesus was taken up from us. For one of these must become a witness with us of his resurrection."
23 So they proposed two men: Joseph called Barsabbas (also known as Justus) and Matthias.
24 Then they prayed, "Lord, you know everyone's heart. Show us which of these two you have chosen
25 to take over this apostolic ministry, which Judas left to go where he belongs."
26 Then they cast lots, and the lot fell to Matthias; so he was added to the eleven apostles. (NIV)

The above verses lead in the direction of argument  that Judas did (was obedient) his part in fulfilling the mission of Jesus. Consider the following conclusion from the same source of the verses:

To summarize, be careful where you place Judas. He did the will of the Father and fulfilled the Scriptures. Peter, who we all love, tried to prevent Jesus' crucifixion and was called "Satan" by our Lord. Peter, who was not mindful of the will of God, was restored. Was it not Jesus who said, ""For whoever does the will of My Father who is in heaven, he is My brother and sister and mother." (Matthew 12:50) Be careful about placing Jesus's brother, Judas, in Christendom's "hell." One day you may have to look up to Judas, instead of looking down on him. Peter denied him three times in one night while Judas declared Jesus innocent in front of the High Priesthood. Judas had a very important job in the Kingdom of God. For three and one half years, as a Priest he inspected the Lamb of God as an unbiased man. He was not "one of them" a Galilean. He was the outsider. He did his job perfectly. If Judas really wanted to mess things up, he could have agreed with the High Priesthood and called Him a "blasphemer" who claimed to be the Son of God when He really wasn't. But Judas declared the Lamb spotless and unblemished, the Perfect Passover. Thank you, Judas, for not only being a hearer of the Word, but also a doer of the Word. Thank you, Judas, for giving the redemption money which purchased the Potter's field; a place for strangers in the land of Israel and the silver which speaks of the redemption of the family of Adam who sold himself as a slave to sin. You may not like how Judas got that money, but you should rejoice in what it did for you.

            I return again to John 16.1: “I have said these things to you to keep you from stumbling.” Jesus knows that those who follow him will be sorely tested, put out of the synagogues (1), killed (2) by those who think “they are offering worship to God” (3).  In short, true followers of Jesus will be persecuted much in the same way as he. Jesus tells his disciples in advance what they should expect: “But I have said these things to you so that when their hour comes you may remember that I told you about them” (4).

    Jesus has much to say to his disciples but understands they cannot bear reality unaided by the Spirit: “I still have many things to say to you, but you cannot bear them now” (12).  Compassionately then, he summarizes:

11      “A little while, and you will no longer see me, and again a little while, and you will see me.” 

His disciples, of course, do not understand, and Jesus reads their hearts and speaks to their unuttered questions directly:

12      They said, “What does he mean by this ‘a little while’? We do not know what he is talking about.”  19 Jesus knew that they wanted to ask him, so he said to them, “Are you discussing among yourselves what I meant when I said, ‘A little while, and you will no longer see me, and again a little while, and you will see me’?  20 Very truly, I tell you, you will weep and mourn, but the world will rejoice; you will have pain, but your pain will turn into joy. 

This is the point where Jesus introduces the figurative labor (which is pain-filled) that results in new creation (and rejoicing).  In short, Jesus himself must suffer the pains of the birthing process to effect new creation.  Seeing that his disciples fail to understand, Jesus speak to them plainly:

25 “I have said these things to you in figures of speech. The hour is coming when I will no longer speak to you in figures, but will tell you plainly of the Father.  26 On that day you will ask in my name. I do not say to you that

I will ask the Father on your behalf;  27 for the Father himself loves you, because you have loved me and have believed that I came from God. †  28 I came from the Father and have come into the world; again, I am leaving the world and am going to the Father.”

29 His disciples said, “Yes, now you are speaking plainly, not in any figure of speech!  30 Now we know that you know all things, and do not need to have anyone question you; by this we believe that you came from God.”  31 Jesus answered them, “Do you now believe?  32 The hour is coming, indeed it has come, when you will be scattered, each one to his home, and you will leave me alone. Yet I am not alone because the Father is with me.  33 I have said this to you, so that in me you may have peace. In the world you face persecution. But take courage; I have conquered the world!”

LS7 — 16:4b-19top

a 4b-5a "I did not say...But now I am going to him who sent me;

b 5b yet none of you asks me, ‘Where are you going?’

c 6 ...because I have said these things..., sorrow has filled your hearts.

d 7-11 ...because I go to the Father,...you will see me no more...

e 12 "I have...many things to say...you cannot bear them now.

f 13a ...the Spirit of truth...will guide you into all the truth;

g 13b ...whatever he hears he will speak, and...declare to you

g¢ 14 He will...take what is mine and declare it to you.

f¢ 15 ...I said...he will take what is mine and declare it to you.

e¢ 16 ...you...see me no more;...a...while, and you will see me."

d¢ 17 ...‘...you will not see me...and...because I go to the Father’?"

c¢ 18 "What does he mean...? We do not know what he means."

b¢ 19a Jesus knew that they wanted to ask him;

a¢ 19b ...he said to them, "...A...while, and you will not see me..."

LS8 — 16:20-33

a 20a ...you will weep and lament, but the world will rejoice...

b 20b You will be sorrowful, but your sorrow will turn into joy.

c 21 ...she has sorrow...she no longer remembers...for joy that a child...

d 22 ...you have sorrow now, but...your hearts will rejoice...

e 23-24 ...if you ask anything of the Father...you have asked nothing...

f 25 ...I...no longer speak...in figures but tell you plainly...

g 26-27 ...you...loved me...believed...I came from the Father.

g¢ 28 I came from the Father and have come into the world...

f¢ 29 ..."Ah, now you are speaking plainly, not in any figure!

e¢ 30 Now we know that you...need none to question you...

d¢ 31-32 "...The hour is coming...when you will be scattered...

c¢ 33a I have said this to you, that in me you may have peace.

b¢ 33b In the world you have tribulation;

a¢ 33c but be of good cheer, I have overcome the world."

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