A Bachur once came to the Klausenberger Rebbe zt'l and told him that he had been expelled from Yeshivah. The Klausenberger Rebbe summoned the mashgiach of the Bachur’s yeshiva and asked for an explanation. The mashgiach told him all the bad deeds the boy had committed, and concluded, “It’s impossible to keep him in the yeshiva if he does these things.” “That’s true,” the Rebbe agreed, “but I spoke with the Bachur, and he told me that he’s ready to change.” The mashgiach said in exasperation, “This Bachur promised me a thousand times that he will improve, but he never keeps his word.” The Rebbe held his white beard and said, “Throughout the many years of my life I promised Hashem even more than a thousand times that I would improve, and I haven’t done so yet. According to what you’re saying, I should give up. But, actually, as long as a Yid lives, he still has potential to improve his ways.”
In the beginning of Parashah, Rashi cites a number of explanations of the Pasuk “BeReishit Bara Elohim Et HaShamayim Ve’Et Ha’Aretz”. One of his explanations is “Bishvil Yisrael SheNikrau Reishit;” Rashi is explaining that “Be Reishit”, for the Jewish people, “Bara Elohim Et HaShamayim Ve’Et Ha’Aretz”. Why is Yisrael called Reishit? One answer given is that the essence of Klal Yisrael and of every Yid is their ability for renewal, for Hitchadshut. This is hinted in the word Reishit, a beginning. After the Yamim Noraim have passed, we come back to everyday life, have we really changed that much? What if we have started to sense that we are going back to our old ways? Comes along the first word of the Torah, “Bereishit,” to remind us we have the ability to to begin again, to renew ourselves.
In Seifer Yechezkel, the Prophet says to the Jewish people “Throw off all of your Aveirot, and make a new heart and a new spirit for yourselves” (18:30). A Klal Gadol in Avodat Hashem is to understand that although we have low points and commit Aveirot, we should always make a new heart and a new spirit for ourselves. How does one accomplish this? Rebbe Nachman in Sichot HaRan (Os 26), Rabbeinu Yonah in Yesod HaTeshuvah, and the Chovot HaLevavot (Shaar HaBechinah 5) write that one needs to act as if he has forgotten his past, leave the Aveirot behind and move forward in your Avodat Hashem, despite your Aveirot. If not for the ability to forget, a person would never be free from his sadness. Yishai Ribo beautifully sings about this concept: “And if a man could remember the flaws, the shortcomings, all the transgressions, all the wrongdoings; he would give up right away, because he wouldn't be able to bear the bitterness, the sin, the shame, the missed opportunity, the loss.”
This doesn’t mean to neglect your past Aveirot and pretend you don’t need Gedarim to ensure you won't fall again, but one should not let his past affect the future of his Davening and learning of the Torah HaKedoshah. Rav Kook in Orot HaTeshuvah (Ch. 13:9) and the Piacezna Rebbe (Mevo HaShaarim Ch 10) speak about how Teshuvah is about the future: what can I do now, at this very moment and onward. This echoes what is taught in Parashat Eikev: “Ve’Atah...Mah Hashem Sho’el Mei’Imach,” “And now...what does Hashem ask of you” (Devarim 10:12). “And Now”, not the past. The Rebbe, Reb Boruch of Medzibuz, taught regarding this pasuk, “And from now, I'll be a Yisrael”. This idea is also alluded to in the very first letter of the Torah: Bereishit Rabbah 1:10 writes that the letter ב is closed from behind, above, and below, but open looking forward. One reason for this is to remind us that a person must also look forward and not backward; use the past to improve your future, but don’t let it affect your future.
Reb Zusha, a master of Teshuvah, would record his “failings” in a notebook. Each night, before going to sleep, he would cry and plead for forgiveness and say that he would begin again tomorrow. Reb Zusha would then stop and think and say, “but I said that last night, and I didn’t improve today, so how can I say that again tonight?” Reb Zusha would think for one more moment and again say, each night, “but now I really mean it”.