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High Holidays 5780 Day 2 Rosh Hashanah Sermon-Why so challenging

Rosh Hashanah Day 2- 5780  Rabbi Kami Knapp

Why Is Teshuva So Challenging?

Day 2

Teshuva. In today’s sermon I want to address the questions: Why is teshuva so challenging? What am I meant to be doing when doing teshuvah? And why start now…isn’t that what Yom Kippur is for?

The definition of teshuvah is: a Hebrew word translated as “returning.” Teshuvah carries a weighty definition and it is hard to unpack this depth when translating the word into English. The English word repentance does not quite suffice, it does not address the complexity of repentance, the process, or the goal of teshuva, which is to seek atonement so that we will return. Return to what you may ask, that is specific to the person. Perhaps it’s a return to an authentic self. Perhaps it’s a return to health or healthy relationships. Perhaps it’s a return to putting ourselves first before others. 

Why start this work now…Isn’t Yom Kippur the day we do teshuvah? This assumption that we do teshuvah on Yom Kippur is based on a misunderstanding of the definition of teshuvah, conflating teshuvah with atonement. Teshuvah is to return, it is a process. Atonement is repentance, an action. In Torah, teshuvah is not mentioned in connection with Yom Kippur.

Leviticus 16: 29-30

כט  וְהָיְתָה לָכֶם, לְחֻקַּת עוֹלָם:  בַּחֹדֶשׁ הַשְּׁבִיעִי בֶּעָשׂוֹר לַחֹדֶשׁ תְּעַנּוּ אֶת-נַפְשֹׁתֵיכֶם, וְכָל-מְלָאכָה לֹא תַעֲשׂוּ–הָאֶזְרָח, וְהַגֵּר הַגָּר בְּתוֹכְכֶם. 29 And it shall be a statute for ever unto you: in the seventh month, on the tenth day of the month, you shall afflict your souls, and shall do no manner of work, the home-born, or the stranger that resides among you.
ל  כִּי-בַיּוֹם הַזֶּה יְכַפֵּר עֲלֵיכֶם, לְטַהֵר אֶתְכֶם:  מִכֹּל, חַטֹּאתֵיכֶם, לִפְנֵי יְהוָה, תִּטְהָרוּ. 30 For on this day shall atonement be made for you, to cleanse you; from all your sins shall you be clean before the LORD.

The Torah speaks of Yom Kippur as the day in which we seek atonement, not one in which we engage in teshuva. Yom Kippur is actually the day when we are meant to have finished our teshuva and returned to authentic selves. On Yom Kippur we present our authentic selves to G-d, to our community, and to ourselves, and we base our new year on our return. We have repaired our wrong doings with others and G-d. We stand before G-d and say: “I come to you today as my authentic self, a self which does not represent the wrong doings I have done this past year.”

Since we engage in atonement on Yom Kippur and not teshuvah, when do we start teshuvah? We are meant to engage in teshuvah throughout the entire year and in the month of  Elul leading up to today, we double down on our efforts. When we reach this moment, Rosh Hashanah, this is our final flag that indicates, atonement is coming. But, if you have not yet engaged in teshuvah or haven’t focused as closely on it as you would have liked, do not be deterred. With the shofar sound we are now awakened and called to do this work. Before addressing the question: why is teshuva so challenging, first let’s explore how one goes about doing teshuvah. Maimonides (a 14th century Sephardic Rabbi gives us a step by step process as to how to do teshuva.

Step 1. Azivat ha-chet — stop doing the bad action 

Step 2. Charatah — remorse for having done the bad action 

Step 3. Viduy — verbal confession 

And finally, step 4. Kabbalah l’atid — resolving, and making a plan, to never repeat these actions

As pointed out in a recent adult education class on Elul, someone noticed that Maimonides steps to teshuvah is interesting in that we first stop doing the action before feeling remorse. We have all heard that small voice in our head or even a small feeling that indicates to us, something about this is not right. Maimonides highlights that we must first be in tune with ourselves to tap into that voice who says something isn’t right. I would argue that this is Maimonides way of giving us a tool for not only doing teshuvah but preventing it from happening in the future. In other words we cultivate our inner values radar so that perhaps we can avoid wrongdoing all together. 

As to the question- What am I meant to be doing when doing teshuvah?

Our tradition stresses that there are two types of teshuvah: between human and G-d, between human and human. “Neither repentance nor the Day of Atonement atone for any, save for sins committed between man and God…but sins between man and man, for instance, one injures his neighbor, or curses his neighbor or plunders him, or offends him in like matters, is ever not absolved unless he makes restitution of what he owes and begs forgiveness of his neighbor… He is obliged to pacify him and to beg his forgiveness…” (mishneh torah, Repentance 2:9)

Therefore, the Day of Atonement only nullifies one’s sins between humans and G-d. Those sins done human to human only are nullified once people have made amends. Sins between humans require action to repair what is broken. Therefore, why start teshuva now? One answer is that without going through the actions of teshuvah with other people, ultimately on Yom Kippur all of our sins will not be forgiven.

Both forms of teshuvah: between humans and between humans and G-d. Both forms, we are meant to engage in throughout the year. We find this is our liturgy outside of the holidays with prayers such as: the bedtime shema which asks for forgiveness for all wrong we do throughout day, and the prayer before death, vidui, which is a request to cleanse our wrongdoings before we move outside of our bodies. But during the ten days of teshuva, we focus on both, sins between one another and sins between us and G-d. We insure that we have repaired our relationship with those around us, and repaired our relationship with G-d.

So why start today?

Rabbi Kruspedai said that Rabbi Yoḥanan said: Three books are opened on Rosh HaShana before the Holy One, Blessed be He: One of wholly wicked people, and one of wholly righteous people, and one of middling people whose good and bad deeds are equally balanced. Wholly righteous people are immediately written and sealed for life; wholly wicked people are immediately written and sealed for death; and middling people are left with their judgment suspended from Rosh HaShana until Yom Kippur, their fate remaining undecided. If they merit, through the good deeds and mitzvot that they perform during this period, they are written for life; if they do not so merit, they are written for death. (Talmud Rosh Hashanah, 16b)

I would argue that most, if not all, people fall into the third category: one of the middling people whose good and bad deeds are equally balanced. So, from a basic perspective, we must engage in this work today, because we have seven days to “plead our case as to why we should be written into the book of life.” Let me digress for a moment about this concept of being written into the book of life or death.

For most of us, this concept of being written into the book of life or death may be uncomfortable. Let me suggest a different view. Let us use the metaphor of the book of life to symbolize finding, returning and living our authentic selves. Because ultimately living our authentic self is that which brings life. We feel more alive when living out who we truly are, our values, and engaging from an authentic place. We have ten days to “attempt to be written into the book of life” because…our Jewish tradition, reminds us that one cannot truly find their authentic self unless we repair the broken bits within us. Our tradition demonstrates through it’s time that only by repairing ourselves and our relationships can we stand as our authentic self on Yom Kippur and only then can we begin to regrow. 

Why start now with teshuvah? Because we also have time to make a choice. Do we want to repair ourselves, with others, and with G-d so that we may return to our authentic self (the book of life) or do we want to remain where we are, complacent, without remorse, with fractured selves ( the book of death). We are given a gift in these ten days, especially now as we end Rosh Hashanah: choice, we choose, we decide. 

And we finally arrive at our final and maybe most important question: Why is teshuvah so hard?

Teshuvah is hard because the process is not easy. Because it is not easy many become complacent and do not engage in the process of teshuva for numerous reasons:

We must confront ourselves and acknowledge that we did wrong.

We must subdue our egos which push us to think we are always right, that we know better.

We must acknowledge, come to terms with, and participate in change and change is SO hard.

This is a scary process because there is so much unknown. It begs the question: what happens when…

And for many of us, it is hard because we are extremely self-conscious. We tell ourselves, I don’t know enough to do teshuvah, I didn’t pay attention in Hebrew school, what if I don’t do it correctly, what if I am rejected?

Therefore, we attempt to seek forgiveness with one or two people and then say it wasn’t, I wasn’t so bad this year. The process of teshuvah is hard and well, risky.

But we must not allow ourselves to become complacent, we have support to do this difficult work. Our tradition builds in a support system for us. We are not alone in doing this work. We all are engaging in teshuvah this time of year and our tradition dictates that we come together as a community on Rosh Hashanah and Yom Kippur. We come together to hold each other accountable to the teshuvah process and we return on Yom Kippur, together, to acknowledge and witness the hard work we have done. At the end of Neilah, as the shofar blows everyone stands grounded in their authentic selves and together we turn to renewal. We return to being a better friend, colleague, partner, parent, and all around person.

I invite you to do this work in parallel with me for the next seven days. Check in with one another, repair relationships here in our community. I ask you to join me on Kol Nidre, poised to present all that we have erred in so that we can together, cast them off, so that we may be together in authentic community. And only then…we party in the Sukkah!

B’hatzlacha and Shanah Tovah


Extra texts:

“It is, therefore, necessary for every man to behold himself throughout the whole year in a light of being evenly balanced between innocence and guilt, and look upon the entire world as if evenly balanced between innocence and guilt; thus, if he commit one sin, he will overbalance himself and the whole world to the side of guilt, and be a cause of its destruction; but if he perform one duty, behold, he will overbalance himself and the whole world to the side of virtue, and bring about his own and their salvation and escape, even as it is said: “But the righteous is an everlasting foundation” (Prov. 10. 25), it is he, by whose righteousness he overbalanced the whole world to virtue and saved it.” (Mishneh Torah Repentance 3:4)


A person’s life is perfected by developing his inherent character. And since one’s still-undeveloped character lacks insight, sin is guaranteed along this path of development. “There is no righteous person in the land who will commit good and not sin.” [Kohelet 7:20] On the other hand, eliminating one’s natural character in order to prevent sin is itself the greatest sin, [regarding which the Torah says of the nazir in Bamidbar 6:11,] “He shall atone for his sin against life.” Therefore, Teshuvah repairs the damage [caused by sin and trying to be someone you are not] and restores the world and this person’s life to its root, precisely by helping the inherent character to develop. – Rabbi Abraham Isaac HaCohen Kook (Orot HaTeshuvah 5:6))