In Parshat Behaalotcha (Bamidbar 10:29), Moshe tells Yitro, his father in law, “We are journeying to the place about which God said ‘I will give it to you,’ come along with us and we will treat you well, for God spoke of bringing good fortune on Israel.”
Why did Moshe include himself in the group that would be entering the Land if he would not be permitted to enter?
Rashi’s answer is that the decree that Moshe would not enter the Land was only issued after the episode of “Mei Meriva”, “The Waters of Dispute” when Moshe hit the rock instead of speaking to it as God had commanded. When Moshe spoke to Yitro, it was before “Mei Meriva” and therefore he believed that he would enter the Land.
Rashi’s interpretation of Shmot 4:13 says that Moshe already knew that he would not be the one who would lead B’nei Yisrael into the Land. However, he thought that he would still enter the Land as an ordinary Israelite. Rashi’s view conjures up images of a rabbi emeritus that remains with their congregation after retirement.
In Shmot 6:1, “God said to Moshe, ‘Now you will see what I will do to Pharaoh, for by My strong hand he will let them go, and by a strong hand, He will drive them out of His Land.’” Rashi points out that Moshe would see what would be done to Pharaoh (now), but not what will be done later to the kings of the seven nations in the Land of Cnaan.
Why did Moshe still think that he would be entering the Land?
Moshe felt that he would at least set foot in the Land even if he would die before the conquest.
After the splitting of the Red Sea, in “Az Yashir” (The Song of the Sea) Shmot 15:7, Moshe sang “You will bring them and implant them in the mountain of your inheritance.” According to Rashi, by saying “them”, Moshe is excluding himself from those who would be entering the Land.
Why would Moshe exclude himself, if he still thought that he would be entering the Land?
According to Mizrachi, the lyrics of “Az Yashir” were revealed to Moshe by prophetic inspiration and therefore he recited them exactly as they were revealed.
Gur Aryeh states that Moshe thought that the decree had not been finalized, so he could still pray for its reversal. For this reason, he sang the song as God intended hoping to reverse the decree later through prayer.
Even though Moshe received many hints from God that he would not be entering the Land, he continued to grasp on to the hope that he would at least have the opportunity to set foot in the Land, even for a brief moment.