Yaakov seems to be asking Hashem for something that Hashem had already granted him. Hashem had previously told Yaakov, “I will not forsake you.” What compelled Yaakov to question his future relationship with Hashem? Horav Nissan Ha’Meiri, Shlita, suggests that Yaakov was asking that Hashem grant him and his descendents the resolve to maintain perspective of the true source of blessing. Regrettably, when one falls on “tough” times, he tends to blame his lamentable state upon Hashem. When the situation changes and he is blessed with success, he attributes this newfound good fortune to his own wisdom and capabilities.
In contrast, Yaakov was secure in Hashem’s benevolence towards him. His concern was in regard to his own nature. Would he accede to the blandishments of the yetzer hara, evil inclination, and attribute his success to his own proficiency? Or would he have the necessary fortitude to overcome the natural tendency to exaggerate his own self- importance? Yaakov, therefore, asked Hashem “to be with Him,” to grant him always that inner strength to recognize the true source of his success — Hashem.
