As a young man he felt he deserved the birthright more than Esau did, and he proceeded to secure it. He went along with his mother’s view that he, not Esau, should have Isaac’s blessing, and he and Rebekah succeeded in making it his.
He paid dearly for his ambition. Banishment from home, exploitation by Laban, a struggle with an unknown assailant, a difficult reunion with his brother – his life was Sturm und Drang.
Yet along the way he founded a family and accumulated possessions, and now he turns to God and says, “I am not worthy of all the mercies and the truth which You have shown to Your servant” (Gen. 32:11).
The sages say (Sotah 5a), “A talmid chacham should have only an 8th of a measure of pride”. Rabbi Avraham of Strettin pointed out that it is the 8th verse of the 8th sidra (Vayyishlach) that tells us of Jacob’s unworthiness and humility.
The Talmud does not tell us that one should have no pride at all. To think so little of yourself that you lack the slightest self-pride is nothing to be proud of!
But there is a human tendency to over-value yourself and to expect both God and human beings to clap and stand up when you walk by.
A healthy dose of self-deprecation is not a bad thing, nor is the ability to laugh at yourself and not take yourself too seriously.