Feeling overwhelmed with too much teshuva to do

Question

I'm having practical difficulty with something that seems to be a contradiction to me.

On the one hand, we're told that practical advice for Elul/RH/YK is to take on a single small thing to improve on, not even necessarily for the whole year. (I've also heard 2 things - 1 bein adom lamokom and 1 bein adom lachaveiro.)

On the other hand, we're supposed to have everything sorted so we've stopped all our aveiros and are keeping all mitzvos before we die, otherwise we'll just get sent back again. If we take the above approach, that's never going to be enough progress.

I personally often feel like I'm going backwards, that each year I'm doing worse than the previous and it is a constant battle against the currents. I feel like each year, I'm a year older, a year less to get myself sorted and polished up before I have to stand before Hashem in final judgement, and I feel like there is nothing like enough time even if I live to over 100. Every year I feel more anxious at this time of year to the point where the last few years I've been feeling physically ill from anxiety (not from fasting) on YK. (I do suffer from anxiety anyway)

There are plenty of shiurim and sefarim that talk about the seriousness of Elul/RH/YK and how much we need to daven and work on ourselves. What sources are there to help reassure us that we're not on an impossible task, and how we can cope with the burden of it?

Answer 1

First of all, I must compliment you on a question that displays an important level of sensitivity to the issue.

Rav Yechezkel Levenstein in his sefer Ohr Yechezkel on Elul asks your question. His response is that G-d expects every person to achieve the growth possible to them each year, so that they reach their potential over time. Compare it to paying off a loan in installments: every year, you will have to have made progress on the payments, but the entire loan can be paid off over a longer period.

Then comes the difficult question of what is actually expected of that person. This is where having a Rebbe or Rav is invaluable. One must do the introspection, but it is also crucial to get personalized advice from a wiser mentor.

One thing I would recommend is to look for areas to improve upon [for example: dedicate more time to learning; improve your concentration during tefillah; work on a specific character trait, etc.] and set as your goal to work on a specific area and monitor your progress. Make whatever specific kabbalos you choose be part of working on that area. Have in mind that you may have to be flexible on the specifics, but you will keep improving in that area. If you decide there is a better way to go about your goal, that's ok and probably natural. If you feel that your original kabbalah was too big or too small, adjust accordingly. If you feel you are ready for the next step, take it.

Hatzlacha Rabba and a great year to everyone on here!

Answer 2

*this is from a recent article on aish. com: I hope it helps.

"...The Neilah service – the peak of Yom Kippur. Our last opportunity to gain forgiveness and atonement. But it’s not just a time of desperate pleading for mercy. It’s also a time when G-d reminds us that He wants to be merciful. He wants us to repent and come back to Him.

“You reach out a hand to willful sinners and Your right hand is extended to those who return,” states the section following the day’s final Vidui Service (The Viddui, which means “confession,” is a prayer recited throughout he Yom Kippur liturgy).

When we attempt the teshuvah process, our yetzer hara (evil inclination) hurries to implant insidious voices of despair in our minds. “Look at you! You’ve strayed so far. You’re irredeemable. How can you even dream of returning? G-d can’t possibly want you back!”

Neilah furnishes an answer to those voices: “You’re wrong! God wants us to return to Him no matter what state we’re in! He loves us, desires us and waits for a relationship with us! We can do teshuvah. We’ll never be too far gone.”

This idea is ultimately the most important takeaway of the High Holiday Season. G-wants a relationship with us. He never gives up on us, no matter how far we've strayed. During this year's Neilah service, let’s take that message in. Let’s recognize just how important we are in G-d’s eyes. Instead of feeling stuck living as people we don’t want to be, let’s live up to the way God sees us. Let’s start returning – that’s all that He wants..." (full article at https://aish.com/meaningful-yom-kippur-at-home/)

Answer 3

While you didn't explain your personal situation, there's a mistake people make that you may be making as well.
The Rambam says at the beginning of Hilchos Teshuvah (https://www.sefaria.org/Mishneh_Torah%2C_Repentance.1.1?lang=bi&with=all&lang2=en)

כָּל מִצְוֹת שֶׁבַּתּוֹרָה בֵּין עֲשֵׂה בֵּין לֹא תַּעֲשֶׂה אִם עָבַר אָדָם עַל אַחַת מֵהֶן בֵּין בְּזָדוֹן בֵּין בִּשְׁגָגָה כְּשֶׁיַּעֲשֶׂה תְּשׁוּבָה וְיָשׁוּב מֵחֶטְאוֹ חַיָּב לְהִתְוַדּוֹת
If a person transgresses any of the mitzvot of the Torah, whether a positive command or a negative command [ital. mine] - whether willingly or inadvertently - when he repents, and returns from his sin, he must confess...

The Rambam goes on to explain how to do viduy, how to do teshuvah that allows the viduy. He talks about the obligation to do it before Yom Kippur, and how we are judged on Rosh Hashana.
Much later, starting in perek 5, the Rambam begins to speak at length about free will, our ability to change anything at all about ourselves, and finally - in perek 7 - our obligation to do teshuvah even on bad midos.
I think people mix these up. That second one is a long process (see his Hilchos Deios), perhaps a lifetime process, the process of becoming better and better. No one expects you to finish it before Yom Kippur.
Remember how the Rambam began: "If a person transgresses any of the mitzvot of the Torah, whether a positive command or a negative command..." That is what we are required to do each year, as soon as possible really. We are supposed to notice when we mess up badly, catch ourselves, and make sure it doesn't happen again.
We should not forget to do this, not let it get swamped by the overwhelming idea of fixing every single thing about ourselves that we should improve.
You mentioned, "take on a single small thing to improve on". That's for the second process, for building yourself up gradually. If someone had a serious collapse we don't tell them that. We tell them, Get up right away, get the help you need. You don't want to stay where you fell. Let's find ways to protect you from its happening again.
How often have you heard drashos that take for granted that right after Neilah, most people are going to go back to where they started? It's not supposed to be that way. We are supposed make sure that we are shomrei Torah and mitzvos, make sure that when we did mess up, we fix it and find ways to make it stay fixed. That's possible, because we aren't talking about an ingrained habit of our character, we're talking about something done wrong, carelessly, once. Or twice, ח"ו, but then it gets harder, so don't wait!
Or drashos about how very hard is it to have charatah today? Well, of course it's hard, if you're talking about bad midos that you haven't fixed yet and will need to continue working on for years. But charatah for something you are shocked that you ever did, that you never imagined you could have done? That charatah is natural.
I feel that this could make a big difference to people. If they do this, even if they have a million other things to fix, they are true בעלי תשובה and שומרי מצות. And they have fulfilled the mitzvah of teshuvah.
-Update: I was reading Pirkei Avos, "נדרים סייג לפרישות" - oaths are a [helpful] fence for building self-control. One way to understand this, maybe, is that nedarim are a tool to convert some part of the "working on oneself" process, which is fuzzy and slow, into issur v'heter, which is more clear and sharp-edged.

Answer 4

As the Mishnah says in pirkei avos- your job is not to complete the work, but you have no right to quit either. G-d has designed you for the specific job of being you, and no amount of self change-good or bad- can effect that. As the alter rebbe says at the beginning of iggeres hateshuvah, teshuvah is the abandonment of sin and resolve to do better, in a nutshell. Once you do, you just have to serve G-d with joy and sincerity and a desire to be close to him, and the rest follows automatically. I highly recommend learning all 12 perakim many times, as it really gives you a direction in how to serve G-D

Answer 5

Yours is not an unusual condition and was a similar concern and famously recorded in the name of Rabbi Meshulam Zusya of Anipoli in the daily guide of Chassidic teaching called HaYom Yom starting from the 3rd of Tishre where it say:

The tzadik R. Meshulam Zusya of Anipoli said that he could not attain the heights of such a teshuva; he would therefore break down teshuva to its components, for each letter of the word teshuva is the initial of a verse:

T: Tamim - "Be sincere with the Eternal your G‑d."

Sh: Shiviti - "I have set G‑d before me always."

U: V'ahavta - "Love your fellow as yourself."

V: B'chol - "In all your ways, know Him."

H: Hatznei'a - "Walk discreetly with your G‑d."

His approach to solving your problem was so significant that the Alter Rebbe went on to concisely explain for the average individual what Meshulam Zusya’s approach means practically for everyone else.

Those explanations are found in the same book for the 4th of Tishrei through the 8th of Tishrei.

G-d bless you and may you be written for a good and sweet year in all things for the coming year.