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This passage uses actual life experiences that would have been very familiar to Jesus' followers - the care of sheep. It was also widely and well established as an image to describe the role of God, kings, Moses, and other leaders in their care of the people (who are similarly also described as being the sheep).
Paradoxically, actual shepherds were scorned and believed to be untrustworthy and dishonourable. They were smelly; they worked at night; they worked in the hills among wild animals and wild people (bandits and other outlaws); they were away from their homes and women and so did not watch over and guard them as honourable men did.
Nonetheless, in Mediterranean culture, "a good shepherd" was an honourable way to describe a "a good leader."
This passage is full of details abut the actual care of sheep.
"Thief and a bandit" - One of the real roles of a shepherd is to PROTECT the sheep from theft, injury (e.g., by falling or getting caught in rocky clefts), attack by wild animals, loss by separation from the flock, and disease.
"Sheepfold or pen, fence, and gate" - Sheep were enclosed for safety at night. Enclosures could be in the village, or caves or other structures in the hills.
Often the sheep of more than one shepherd would be enclosed in the same pen. In the morning, when it was time for the sheep to be separated and taken out to graze, it was the common practice for each shepherd to give each of his sheep a name, and to call his sheep out of the combined flock by name.
"Knowing, naming, calling, hearing" - Another role of the shepherd is to KNOW his sheep individually - by name - and be able to call them out of a crowd: to maintain their relationship directly with him. In John, "know his voice" does not mean simply recognize; it implies a deep bond, attachment and connection.
"Leading, following" - A third role of the shepherd is to be brighter than the sheep: to know the landscape in a way they cannot; to be aware of both sources of sustenance and of danger that they cannot; to be able to plan and anticipate in a way that they cannot; to be trustworthy, loyal and caring in a way they are not. In other words, to LEAD the sheep.
"Gate, entering, going out, pasture, saved, abundant life" - And finally, in the last section of the passage, the metaphor changes from role of the shepherd to that of the gate. Jesus is the passageway - the boundary transition point - through whom we are able to find abundant life. In this context, "abundant life" does not mean "lots of toys." It refers to the quality of life that comes through attachment to Jesus - believing / trusting into Jesus; abiding in Jesus; eternal life.
This passage reiterates several major themes in John.
Life. John 20:31 says that the whole purpose of writing down these stories about Jesus is so that we might believe that Jesus is the Messiah, and that through believing we may have life in his name. The question of distinguishing between true life and death is a challenge that runs throughout John.
Who is Jesus? What do you make of him? The true identity / nature / character / purpose of Jesus is made known to those who become his followers and are separated from all others. Often his own closest companions do not get what Jesus is saying, requiring him to repeat his explanations. (See verse 10:6)
Bonding. The purpose of this talking about Jesus is not simply to be better informed about Jesus. The purpose is to be IN Jesus, just as he is in the Father and the Father is in him.