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In the following text Christ seemingly discourages the volunteer who wanted to follow him.In the answer that he gives to the volunteer that of having no place to lay his head is somehow discouraging knowing that he had a home.

Luke 9:57 NASB

57 As they were going on the road, someone said to Him, “I will follow You wherever You go.” 58 And Jesus said to him, “The foxes have holes and the birds of the sky have nests, but the Son of Man has nowhere to lay His head.

Yet in the next verse he gives an invitation to one who did not volunteer to follow him

Luke 9:59 NASB

59 And He said to another, “Follow Me.” But he said, “Lord, permit me first to go and bury my father.” 60 But He said to him, “Allow the dead to bury their own dead; but as for you, go and proclaim everywhere the kingdom of God.”

Why did Christ seemingly discourage the first volunteer?

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Why did Christ seemingly discourage the volunteer in Luke 9:57-58?

If by volunteer, you mean occasional part-time volunteer, then I don't think that Jesus was commenting on such people in Luke 9:58. Jesus was looking for full-time disciples who would dedicate their lives to Christ's works as described in Matthew 10:

37 “Anyone who loves their father or mother more than me is not worthy of me; anyone who loves their son or daughter more than me is not worthy of me.

Jesus knew all men, including the one in Luke 9:

57 As they were going on the road, someone said to Him, “I will follow You wherever You go.”

Jesus probably saw that this volunteer was hasty and rash and didn't know the requirement and costs associated with Matthew 10:37.

Then Jesus issued an invite to a second person in Luke 9:

59 And He said to another, “Follow Me.” But he said, “Lord, permit me first to go and bury my father.”

This second person contrasted the first. He was not quick to follow. He was too slow to follow Jesus. This was no good either:

60 But He said to him, “Allow the dead to bury their own dead; but as for you, go and proclaim everywhere the kingdom of God.”

The lesson is this. Don't be too quick to join. Count the costs first. After you have considered the costs and if you are still willing, then don't hesitate. Don't let your worldly relations or possessions delay your joining Christ's works. Then, you can devote your whole being to follow Jesus without worldly distractions.

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Many wish to tame God, to adjust Him to his own understanding and finality; but Lord is infinite, paradoxical, always eluding nets of human understanding, asking even us to tear apart them, as Peter had to tear apart the fishermen’s nets that he could catch unexpected and unseen amount fishes (Luke 5:6), metaphorically signifying tearing apart our human, limited categories in order to be able to catch “fishes” of divine, unexpected, unlimited knowledge.

That’s why here also He does not dis-encourage the guy, but warns him that to follow Him means to forget about human finite logic and embracing divine infinite logic; warns him that there is a danger of him limiting Him and reducing Him to his human narrowness (like for example seeing in Him a political Messiah only), rather than losing his narrow self to His infinite breadth, for “nowhere to lay down His head” denotes metaphorically awesome and dreadful infinity of God and our doom of blessed restlessness if we follow Him ~

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In the passage in question, Jesus’ words serve to clarify the nature and demands of discipleship. To the one who asks to follow Jesus, he answers that the goal of discipleship is not to reach a specific place but to build a spiritual home for God.

vv. 58 – “The foxes have holes and the birds of the sky have nests, but the Son of Man has nowhere to lay His head.”

So then you are no longer strangers and foreigners, but you are fellow citizens with the saints, and are of God’s household, 20 having been built on the foundation of the apostles and prophets, Christ Jesus Himself being the cornerstone, 21 in whom the whole building, being fitted together, is growing into a holy temple in the Lord, 22 in whom you also are being built together into a dwelling of God in the Spirit. – Eph 2: 19-22

To those who are called to proclaim the kingdom of God but who hesitate, he says discipleship is a commitment that must take precedence over all other responsibilities and attachments.

vv. 59-62 – And He said to another, “Follow Me.” But he said, “Lord, permit me first to go and bury my father.” 60 But He said to him, “Allow the dead to bury their own dead; but as for you, go and proclaim everywhere the kingdom of God.” 61 Another also said, “I will follow You, Lord; but first permit me to say goodbye to those at my home.” 62 But Jesus said to him, “No one, after putting his hand to the plow and looking back, is fit for the kingdom of God.”

Jesus said, “Truly I say to you, there is no one who has left house or brothers or sisters or mother or father or children or farms, for My sake and for the gospel’s sake, 30 but that he will receive a hundred times as much now in the present age, houses and brothers and sisters and mothers and children and farms, along with persecutions; and in the age to come, eternal life. – Mk 10:29-30

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Why did Christ seemingly discourage the volunteer in Luke 9:57?

The parallel account in Mt 8:19-21 tells us that it was a scribe who asked Jesus.

Matthew 8:19-21NASB

19 Then a scribe came and said to Him, “Teacher, I will follow You wherever You go.” 20 And Jesus *said to him, “The foxes have holes and the birds of the sky have nests, but the Son of Man has nowhere to lay His head.” 21 And another of the disciples said to Him, “Lord, allow me first to go and bury my father.”

Jesus sensing that the proud scribe would find the trials and hardships of discipleship difficult, replied: “The foxes have holes and the birds of the sky have nests, but the Son of Man has nowhere to lay His head.”(Vs 58)

Apparently, the uncertainty of where his next meal would come from or where he would live did not go well with the scribe, for there is no indication in the scriptures that he became a follower of Christ.

Luke 9:57-59 NASB

Exacting Discipleship

57 As they were going on the road, someone said to Him, “I will follow You wherever You go.” 58 And Jesus said to him, “The foxes have holes and the birds of the sky have nests, but the Son of Man has nowhere to lay His head.” 59 And He said to another, “Follow Me.” But he said, “Lord, permit me first to go and bury my father.”

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