Parashat Vayishlach begins by telling of Yaakov’s trepidation upon learning that Esav was approaching with an army of four hundred men, and his frantic preparations in advance of this feared encounter. Various sources in the Midrash and commentaries address – explicitly or implicitly – the question of why Yaakov felt afraid, given that God had explicitly assured him when he left Canaan that he would return safely (28:15). One passage in the Midrash, cited by Da’at Zekeinim mi-Ba’alei Ha-Tosafot, explains that Yaakov feared that Esav was worthier of divine support than he was. Throughout the previous twenty years, Yaakov lived far away from his home and homeland, while Esav remained in the Land of Israel and cared for his and Yaakov’s elderly parents. Yaakov thus feared that the merit of these two mitzvot – living in Eretz Yisrael, and caring for parents – tipped the scales in Esav’s favor, such that Esav would receive God’s help to defeat Yaakov, and not vice-versa. These two mitzvot – which Esav fulfilled throughout the previous twenty years, while Yaakov could not – may have given Esav the edge, so-to-speak, in the confrontation that was about to take place.
Later commentators struggled to understand how Yaakov could have entertained such thoughts. Chazal depict Esav as a cruel, heartless, violent criminal, whose respect for his parents was insincere and deceptive, aimed at making a falsely favorable impression. Yaakov, on the other hand, was a sincere, devoted servant of God who was compelled by circumstances entirely beyond his control to flee and leave his homeland. While it is true that Esav fulfilled two important mitzvot over the previous twenty years which Yaakov was unable to fulfill, this was not due to any fault of Yaakov, who, in any event, clearly had many merits to his favor which Esav did not.
The likely explanation (as discussed by Rav Chaim Elazary, in Mesilot Chayim) is that the Midrash here seeks to teach us the perspective with which we are to assess ourselves in relation to others. Our instinctive tendency when comparing ourselves to others is to take pride over the positive qualities that we have and others don’t, and over that which we’ve accomplished and they have not. We naturally tend to look for and focus on ways in which we outshine other people. The Midrash here teaches us to have the precise opposite mindset – to respect, admire and envy the positive qualities and accomplishments of others that we have not achieved. Certainly, we are entitled and encouraged to take pride of our own achievements. However, rather than gloating over them and feeling superior to those who have not reached these achievements, we should instead focus our attention on the aspects of other people’s characters from which we can learn and which we can emulate. Just as Yaakov took note specifically of the two mitzvot which Esav fulfilled for twenty years which he could not, so should we take note of the impressive qualities and achievements of others rather than feeling superior to them because of our own qualities and achievements.