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What If We’re Starting Teshuvah in the Wrong Place?

Sep 09, 2026

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On My Mind

Mrs. Aliza Feder's Newsletter

 

One of the sefarim that I have found most immediately applicable to my life has been Yesharim Darchei Hashem by Rabbi Yonasan Eber. He writes about how to make your avodas Hashem personal (the entire first section of the sefer became the foundation of my Authentic Avodas Hashem course (for more information see here)), and has different sections on the topics of tefillah and teshuvah. 

I was rereading the teshuva section now that the yamim noraim are fast approaching, and I would like to share the following thoughts of his in the hopes that you found this as practically helpful as I did. I’m including the actual quote from Rav Yisroel Salantar in the sources section. 

Here we go:

Rav Eber develops an idea of Rav Yisrael Salanter that seems, at first, almost backwards: When we think of doing teshuva, we automatically zero in on the places that are hardest for us, the mitzvos that we find most difficult. But the most important place to begin doing teshuvah may not be the part that is hardest for us. It may be the part that is easiest.

Rav Yisrael bases this idea on a Gemara in Menachos. The Gemara compares two people who neglect the mitzvah of tzitzis. One wears a four-cornered garment without placing any tzitzis upon it; the other attaches the ordinary white threads but doesn’t include the much more expensive and difficult-to-find techeiles. The Gemara teaches that the punishment for the first- not putting tzitzis on at all- is greater, and explains it with a mashal. A king instructed one servant to bring him a seal made of gold and another to bring him a seal made of clay. Both failed to bring what they had been asked to bring, but the failure of the servant who had been asked for clay was more serious. Gold is difficult to obtain. Clay is readily available. The first servant could at least point to the difficulty of his assignment; the second had almost no explanation for why he had failed.

There is something here that is very important to understand. We usually judge the seriousness of our failures by looking at the intensity of the struggle. Rav Yisrael asks us to take another factor into account: How much was actually being asked of me at that moment? When the temptation was powerful, the circumstances were overwhelming, or the change required enormous strength, the aveirah remains an aveirah, but there was at least a real battle taking place. When doing the right thing would have been relatively easy and we nevertheless did not do it, there is a different kind of claim against us: If it was not particularly difficult, why didn’t you do it?

Rav Yisrael writes in Ohr Yisrael, Michtav 15:

“מה שנקל לפני האדם לקיים, עבירה אחת חמור יותר מכמה עבירות אשר כבד לפניו.”

One aveirah involving something that was easy for a person to fulfill can be more serious than several failures in areas that were very difficult for him.

This is not only a comparison between two different aveiros. Even within one aveirah, there may be many different levels. There are times when we are exhausted, pressured, hurt, angry, distracted, or confronting a powerful temptation, and there are other times when the same behavior would be much easier to control. The external act may look identical, but our degree of responsibility is not necessarily identical. Rav Yisrael explains that every aveirah can be divided into many small and subtle parts, according to the circumstances and the difficulty of the test.

Consider, for example, someone who knows that her tefillah needs work. She may sincerely want to concentrate throughout Shemoneh Esrei, understand every word and arrive at davening on time, but at this point that may feel far beyond her. Because she can’t imagine davening with kavanna for the whole thing, she may continue doing exactly what she has always done. Rav Yisrael would ask her to look more closely. Is there really no part of tefillah in which concentration is easy for her? Could she concentrate on the first few words of Shemoneh Esrei, half of one brachah- even one sentence? Why should the part that is currently beyond her prevent her from changing the part that is easy for her?

The same idea can be applied to someone who struggles with lashon hara. A sweeping resolution never to speak lashon hara is probably not realistic. There may be certain conversations, relationships or situations in which the pull is very strong and she’s not yet prepared to succeed consistently. But are there other people with whom remaining silent is easier? Are there particular hours of the day, types of conversations or subjects in which she could decide that lashon hara is simply not an option? Instead of allowing the hardest part of the nisayon to define the entire struggle, she can identify the parts in which the nisayon is small and begin there.

This changes the way we think about a small kabbalah. We often dismiss a very limited commitment because it doesn’t seem serious enough to qualify as teshuvah. If I still have so far to go, what difference does it make that I concentrated on one sentence, avoided one conversation or changed my behavior during one particular hour? Rav Yisrael tells us that this is not pretend teshuvah. Regarding that particular part of the aveirah, it can be entirely genuine.

Rav Yisrael writes that a person can enter Yom Kippur with a genuine acceptance to abandon the aveirah “בבחינה הקלה לפניו”—in the aspect that is easy for her. In that defined area, she has made a true decision. She has become a baalas teshuvah regarding that part of the behavior, and from there she can ask for the siyata diShmaya to continue moving from one level to the next.

(At the same time, “begin with what is easy” does not mean making twenty-five tiny commitments across every area of life. Rabbi Eber cautions that if someone goes through the entire list of mitzvos and aveiros and selects a small kabbalah from every subject, she is likely to end up maintaining none of them. We still have to think seriously about which areas matter most, giving appropriate weight to the seriousness of different obligations. Then, within one or two important areas, we can search for the part that is within reach right now.)

So maybe that is a more useful Elul question than asking, “What is the biggest thing wrong with me?” We can ask instead: In an important area of my avodas Hashem that needs work, which part is not actually so hard? Where am I failing not because the nisayon is overwhelming, but because I never thought a tiny change was worth it? What small, precisely defined change could I honestly accept and continue keeping even after the Yamim Noraim?

Personally, (me speaking again now, not Rabbi Eber), this is not an idea that comes naturally. Of course I’ve grown up with the ideas of the small, manageable kabbalos but some part of my personality always shrugged it off. I’m much more of a ‘go big or go home’ persona. But something about the way Rav Eber, from Rav Yisroel Salanter, broke this down about the worth of mitvos (and aveiros!) not being the way we usually think about them….well I'm convinced. 

I would love to hear what this idea brings up for you. Is there one “easy area” in which a small but genuine kabbalah suddenly seems possible? You are welcome to reply and share it with me- I would love to be able to pool our ideas for tiny, powerful changes!

And if you would like to think more deeply about how to build an avodas Hashem that is honest, personal and sustainable, my six-part Authentic Avodas Hashem course is available here.

This is going to be the last newsletter until after succos, as our office is closing for the yamim noraim (just kidding, it’s just me:)). Wishing us all a k’siva v’chasima tova and a good g’bentched yar!

Mrs. Aliza Feder

PS if you know of someone who would appreciate this newsletter, or if they would want to know about future class options, please forward this and have them sign up here or though the website!

 

Sources: Yesharim Darchei Hashem by Rabbi Yonatan Eber, “Teshuvah,” pp. 181–184

אור ישראל ט״ו

 

הָאָדָם צָרִיךְ לְחַפֵּשׂ דְּרָכָיו לַעֲשׂוֹת קַבָּלָה חֲזָקָה, כִּמְעַט בְּכָל פְּרָטֵי עִנְיָנָיו, לְהִשָּׁמֵר לְכָל הַפָּחוֹת אֶת אֲשֶׁר נָקֵל לְפָנָיו בְּכָל פְּרָטֵי הַתּוֹרָה וְהַמִּצְוָה, וּבָזֶה יֵשׁ דֶּרֶךְ אֲשֶׁר יְקַיֵּם מִצְוַת הַתְּשׁוּבָה בְּרֹב חֶלְקֵי עֲו‍ֹנוֹתָיו, כִּי הָרִבּוּי בְּהָעֲו‍ֹנוֹת אֵינָם הוֹלְכִים אַחַר הַכַּמּוּת — לְפִי הַמִּנְיָן — רַק לְפִי הָאֵיכוּת, (עַיֵּן רַמְבַּ"ם הִלְכוֹת תְּשׁוּבָה פ"ג) הַיְנוּ מַה שֶּׁנָּקֵל לִפְנֵי הָאָדָם לְקַיֵּם, עֲבֵרָה אַחַת חָמוּר יוֹתֵר מִכַּמָּה עֲבֵרוֹת אֲשֶׁר כָּבֵד לְפָנָיו, וְכֵן בְּאוֹתָהּ עֲבֵרָה עַצְמָהּ חֵלֶק קָטָן מִמֶּנָּה הַנָּקֵל לִפְנֵי הָאָדָם לְקַיֵּם, יוֹתֵר חָמוּר וְעָנְשָׁהּ גָּדוֹל מֵהַרְבֵּה חֲלָקִים אֲשֶׁר בְּהָעֲבֵרָה אֲשֶׁר כָּבֵד לְקַיֵּם:



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