Taking the first step
דרשו יקוק בהמצאו קראהו בהיותו קרוב: יעזב רשע דרכו ואיש און מחשבתיו וישב אל-יקוק וירחמהו ואל-אלקינו כי-ירבה לסלוח
Seek out Hashem where he is found, call out to Him when He is close. The wicked one will abandon his ways, the sinful man his thoughts; he will return to Hashem, who will have mercy on him, and to Our G-d, since He is wont to forgive
The Midrash says that once the Jews started to approach the land of Israel, Moshe pleaded with Hashem that he be allowed to join them. He had recently been barred from entering the land. He asked: “Please can I see it”. Hashem responded by asking how could He annul His decree against Moshe and yet maintain Moshe’s earlier decree? When the Jews sinned during the episode of the spies, Hashem was going to annihilate the nation. Moshe said: “Please forgive them”. Hashem fulfilled his decree. By asking to enter the land, Hashem informed Moshe that it was like he wanted to hold on to a rope from both ends. If Hashem’s decree is nullified, Moshe’s decree can’t stand. Once Moshe heard this, he desisted from his prayers. This Midrash on the surface is astounding. How come one decree is dependent on the other? Why does letting Moshe into the land remove their earlier forgiveness?
A possible approach to this is based on the concept that Amalek, the eternal enemy of the Jews, can only be overcome by a descendant of Rochel. The reason could be because Chazal explain that when Amalek attacked the Jews after leaving Egypt, their success was because Hashem said: “let the ones who are ungrateful exact payment from those who are ungrateful”. Amalek were considered ingrates, and the Jews at that time showed ingratitude after being redeemed from Egypt. The opposite of someone ungrateful is someone who repays evil done to them with good. The paradigm example of this was with Yosef. Despite having his brothers sell him into slavery, he forgave them and helped them settle in Egypt. Only someone the total opposite of Amalek could defeat him. It will have to be a descendant of Yosef, who was the son of Rochel.
When the Jews set off to conquer the Land of Israel, they could have gone in thinking that it was solely their might which would grant them victory. However, they knew that the true merit that would grant them success was their desire to conquer it with the help of Hashem. Since they had this initial desire to fulfill the mitzvah of Hashem and had this trust in His supervision, He went before them to conquer. However, if they had within themselves any fear, any lack of trust, their enemies would have defeated them.
Forty years after Amalek’s first attack in the wilderness, the Jews still feared them. Therefore, if Moshe, a descendant of Leah, had gone with them, they would know that he couldn’t lead them to victory. They would have feared confronting Amalek, and couldn’t go in with full confidence that Hashem would lead them to victory. Their original sin with the spies was a fear of their enemies and a lack of faith in Hashem. If Moshe had insisted in going in, he would have been like holding a rope at both ends. Forgiveness for the episode of the spies was contingent on them not following their old ways. Moshe leading them to war would have caused that. Therefore, it was impossible for Moshe to enter the land with them. Yehoshua, a descendant of Rochel, had to fill Moshe’s place. Only he could defeat Amalek, allowing the Jews to have complete faith in Hashem that they’d succeed.
This approach to success is similar to the internal struggle a person has with their inclinations. First, the person must be inspired to return to their Creator. Only then will there be Divine help from Hashem, who will clear the path for the person. This is true even if the person wronged another and can’t remember who it was to ask for forgiveness. Hashem will inspire the victim to forgive the one who wronged them. Similarly, Hashem helps us to repent in every way necessary. This is what is meant by the verse: “Seek out Hashem where He is found”. Seek out Hashem in any productive manner. Afterwards: “the wicked one will abandon his ways, and the conniver his thoughts”. The ones who willingly desire to change, Hashem will help them. It’s true that every detail of teshuvah, repentance, which helps remove the negative roots in a person, requires great preparation and exertion. However, if the inspiration to change is true, Hashem will help them achieve the deepest level of teshuvah.
 Based on Meshech Chochmah to Deuteronomy 29:3, with help from the Rabbi Kupperman edition and an English translation by Rabbi Yitzchok Adlerstein (http://torah.org/torah-portion/meshech-chochmah-5776-kisavo). The first half of this piece is directly related to this week’s parsha. However, the second half, which was personally more inspiring, seemingly had no relation to the first half. It does relate though to the month of Elul, which is all about preparing for Rosh Hashanah and Yom Kippur. Due a lack of understanding to its relation to the second half, the first half was omitted. However, Rabbi Adlerstein ingeniously weaves the two together. It is clear that his approach is what the Meshech Chochmah intended
 Isaiah 56:6-7
 Devarim Rabbah 7:11
 Numbers Chapter 20
 Deuteronomy 3:25
 Numbers 14:9
 Bava Basra 123b says the descendants of Eisav. This isn’t problematic, since the verses in Tanach that deal with wars between Israel and Eisav always involve Amalek, one of Eisav’s descendants
 Mechilta to Exodus 17:8
 Exodus loc. cit.
 Midrash Eliezer to Mechilta loc. cit. explains that the prohibition to wage war against Eisav’s descendants (Deuteronomy 2:5) originally included all of them. Once Amalek attacked the Jews in the desert, the prohibition no longer applied to them. Instead of being grateful for being spared from war, Amalek decided to use it to their advantage
 This is because right before Amalek came, the Jews were testing to see if Hashem was with them or not (see Rashi to Exodus loc. cit.)
 Genesis Chapter 37
 ibid 50:19-21
 This explains why Moshe told Yehoshua, who was a descendant of Yosef through his son Ephraim, to lead the war against Amalek (Exodus 17:9). See http://parshaponders.com/2017/04/06/pesach-tzav-5777 for more on why specifically the descendants of Rochel are fit to defeat Amalek
 Deuteronomy 8:17
 ibid verse 18
 This explains why he couldn’t be their leader when they entered the land but doesn’t explain why he couldn’t enter the land as an ordinary citizen. See Abarbanel to Numbers 20:1 who addresses this. For other approaches to why Moshe couldn’t enter the land, see http://parshaponders.com/2017/06/28/chukas-5777
 הבא לטהר מסייעין אותו (Yoma 38b)
 A person can’t properly repent until they’ve appeased their fellow (Mishneh Torah Hilchos Teshuvah 2:9)
 Isaiah loc. cit.
 ibid verse 7