For the first time in his career, Moses did not receive a direct instruction from G‑d. When the Jewish people requested that Moses send spies to scout out the Promised Land, G‑d told Moses:

Send out for yourself men who will scout the Land of Canaan, which I am giving to the Children of Israel.1

Rashi, the primary commentary on the Torah, clarifies and explains that the words “for yourself” were not a commandment to dispatch spies. In the words of Rashi:

Send out for yourself: According to your own understanding. I am not commanding you, but if you wish, you may send.

The spies brought calamity upon the Jewish people. When they returned from scoutingThe spies brought calamity upon the Jewish people out the land, they reported that the Jewish people were incapable of conquering the land. The Jewish people wept and called for the appointment of a new leader who would bring them back to Egypt. In response to their rejection of the Promised Land, G‑d decreed that the Jewish people would wander in the desert for 40 years, and the generation of people who were liberated from Egypt would die in the desert. Only the next generation would merit to enter the Promised Land of Israel.

Why did Moses decide to send the spies? Until that point, Moses did not make a move without an explicit instruction from Above. Why did Moses not consider that, by emphasizing that He was not commanding Moses to dispatch the spies, G‑d may have been signaling to Moses to hold back and not send the spies? Why did Moses miss the red flag?

When he heard the words “if you wish, you may send,” Moses was filled with joy. Moses understood that the Jewish people were being asked to climb to greater spiritual heights and exercise free choice. They were now developed to the point where they were capable of performing the will of G‑d, not because they were commanded to do so, but because of their own will and desire. G‑d was opening a new path in Divine service: no longer would there be a direct commandment from Above, for the goal of the Torah is not to superimpose its will, but rather for people to discover that they themselves want to do the right thing.

Until now, the people were shown which path to take: G‑d led them out of Egypt, tookThey would no longer experience Divine revelation them to Sinai, and led them through the desert toward the land of Israel. Once they entered Israel, they would no longer experience Divine revelation guiding their every step. The sending of the spies represented the critically important ability of the Jewish people to decide that they wanted to enter the land, not because of a commandment alone, but because their own will and desire directed them to do so.

This explains why 40 years after Moses sent the first group of spies, Joshua, the student and successor of Moses, once again sent spies, as we read in the haftorah:

And Joshua the son of Nun sent two men out of Shittim to spy secretly, saying, “Go see the land and Jericho. “

The mission of Joshua’s spies was successful. Joshua, despite witnessing the calamity brought on by the spies sent by Moses, took a risk and sent spies. Joshua understood that they could not enter the land without first sending spies. Because we cannot truly transform the earth, we cannot imbue the earth with lasting holiness, unless we do so because of our own desire.2