Jacob did not squander his wealth, though as has been seen, life was a bit wild for him. Like the prodigal in his exile from his father’s house, fortune had eluded Jacob though others had gotten rich at his expense. The son of the famed parable is said to have experienced the effects of destitution, as a terrible famine grips the land. Seeking whatever income he could find, he attaches himself to a citizen of that country, much like Jacob was attached to Laban because of the need to pay him for all of the wives (and children until the wife debt obligation is met), and is sent to feed the citizen’s pigs.
Naturally, as the hearers of Jesus’ parable were predominantly Jewish, and because they would naturally assume that the family in the story is Jewish, they would see this as an attempt by the man to get rid of an unwanted hanger-on, expecting that the young Jewish man would resolutely refuse to lower and defile himself in such a way. This was viewed as a possibility in Laban’s business deal with Jacob, which, based on Laban’s actions after striking the deal, might be taken to have indicated a desire to rid himself of Jacob.
Eventually, while feeding the pigs but while still hungry, the young man in the parable is said to have come “to his senses,” saying “How many of my father’s hired workers have food enough and to spare, but here I am dying from hunger!” (Luke 15:17), and so hatches a plan to return to the home that he had left in shame and dishonor. Similarly, Jacob comes to his senses. With the documented hostility that he is experiencing, he wonders why it is that he remains where he is, when he could return to his father’s house, rather than continuing to serve under a man who clearly did not want him around any longer.
The younger son however, knows that he has shamed himself and his family, and knows that harsh consequence up to and including the possibility of death, await him if he returns to his father’s house. Owing to that, and considering the fact that his father’s hired workers earn enough to feed themselves with money to spare, he devises a plan that will allow him to gain one of those positions, so as to be able to pay back his father over time, and in the process allow him to regain the honor that he had lost. So he says “I will get up and go to my father and say to him, ‘Father, I have sinned against heaven and against you. I am no longer worthy to be called your son; treat me like one of your hired workers.’” (15:18-19)
This is the same thing that can be seen with Jacob. He cannot simply return to the house that he left, covered in shame, having dishonored his father and his brother. He has a brother that has previously declared his desire to kill him, and a father that he greatly dishonored. Therefore he must devise a plan. Clearly, because his father (though it was done unwittingly) passed the covenantal blessing on to him, his primary concern is with the wrath of his brother, thus the planning taking place with the division of the families, and then the gifts of animals, with the message passed along by the servants.
Effectively, with the language that is heard on the lips of Jacob, bowing to the ground as he refers to himself as Esau’s servant while also referring to Esau as “my lord” and telling him that seeing his face is like seeing the face of God, it is almost as if Jacob can be heard saying something like “I have sinned against heaven and against you; treat me like one of your hired workers.”