Good Guilt, Bad Guilt: An In-Depth Guide on the Steps of Teshuva

Teshuva is a miraculous gift, a golden opportunity to retroactively undo our mistakes and even turn them into zechuyot. Yet, the thought of tackling it makes many of us uneasy. It feels uncomfortable, confusing, vulnerable, and intimidating. 

It neednโ€™t be. The steps of teshuva are clearly defined and intensely meaningful to put into practice. With a little mindfulness and true commitment, we can all come into the New Year with a clean slate. Letโ€™s take a deep dive into the steps of teshuva1 and see what we uncover. 

Azivat Hechet: Leaving the Sin

This is obvious and often complete by the time a person does teshuva. It means not being guilty of the transgression one is repenting for while standing before Hashem. The Navi says this plainly: Let the wicked give up their ways.. so as to be forgiven2.

Rambam writes: Anyone who verbalizes his confession without resolving in his heart to abandon it can be compared to one who immerses himself while holding a lizard in his hand.3 

It is considered shameless and utterly audacious to confess before Hashem while being guilty of the very sin.

There is no fooling the Knower of all thoughts. Nobody knows what life will bring and what position they will be placed in, but we can tap into our internal compass to help us figure out if we are carrying a carcass as we immerse in the mikveh of teshuva. Do we feel revulsion at the thought of the sin? Are there any plans, practical or aspirational, anywhere within our psyche to in any way return to our old ways, or put ourselves in a position of amplified challenge? 

Charatah: Remorse

Regret, remorse, guilt. What a difficult set of emotions, annoyances and discomfort we love to avoid. Western culture romanticizes the life of no regrets, the life of no looking back, just do exactly what you want and never dare feel bad about it. As if regret, as an admission of guilt, is a sign of weakness.

One of the most popular modern funeral songs is My Way, the lyrics of which highlight the life of a man who โ€œ…lived a life that’s full/ I traveled each and every highway/ but more, much more than this/ I did it my way.โ€4 It celebrates the life of a metaphorical bulldozer, one who charts his course and marches along it, knocking down potential obstacles by the sheer power of his will. And importantly, he never has regrets. 

Needless to say, thatโ€™s not the Jewish way. When we do wrong, the only way to come back from it is to wish we hadnโ€™t done it. That is the basic understanding of charatah; if I could turn back the clock and undo what I did, or take an opportunity I missed, would I?

This can be difficult in a case where there was a tangible gain of the aveirah. Charatah is a package deal, a true sense that one deeply wishes they have not done the wrong action, including any possible positive consequences. 

Guilt is to the conscience what pain is to the body; it alerts you of something gone awry. It isnโ€™t necessary or helpful to dwell on guilt, nor to cry about it. We might treat it like a toothache or a cramp. Importantly, do not ignore it. Investigate: is this a well-founded emotion? You go to a doctor to tell you whether a cramp is a sign of something serious. If it is, we know what to do with it next.  

Guilt can be driven by egotism. Our reluctance to accept our imperfection means weโ€™re often resistant to recognize that weโ€™ve made a mistake. Often, even with the best of intentions, we can cause harm to ourselves and others. Guilr allows us to feel like we are at odds with the mistake, like it isnโ€™t truly where weโ€™re at, and to not identify with and fix it. Thereโ€™s a sense of virtue in carrying around guilt, enabling us to avoid facing our imperfections.

The trick is to follow the facts and determine for oneself: Is there something here I could have made a better choice about? If yes, we can repent; otherwise, we move on. The important thing is to remember that guilt itself is no inherent mitzvah, but a necessary tool within the process of teshuva.

Vidui: Confession

Confession is the pivotal step in Teshuva, and in some ways its defining point. The source for this step is brought5 from a case of a man-to-man transgression, where the Torah clearly outlines the necessary reimbursement. Nevertheless, confession is crucial: they shall confess the wrong that they have doneโ€ฆ6

The confession must be verbal, and private: it is meant to be between Hashem and man alone7. Coming face-to-face with our sins requires explicitly verbalizing so our own ears can hear it. Surely Hashem knows where weโ€™ve fallen; the power of expressing where we went wrong lies in challenging ourselves to face it objectively, completely, no asterisks or excuses. For this reasons, confession should be elaborated on and profusely detailed, the more one is able8.

A complete confession of guilt is ultimately what brings us forgiveness. It is the point at which we can test if we are truly sorry, absolutely regretful, and have learned our lesson. When thatโ€™s done, the inner work of teshuva is effectively complete. 

Rambam provides us with a clear outline of what a confession might look like:

ืึธื ึธึผื ื”ึทืฉึตึผืื ื—ึธื˜ึธืืชึดื™ ืขึธื•ึดื™ืชึดื™ ืคึธึผืฉึทืืขึฐืชึดึผื™ ืœึฐืคึธื ึถื™ืšึธ ื•ึฐืขึธืฉึดื‚ื™ืชึดื™ ื›ึธึผืšึฐ ื•ึฐื›ึธืšึฐ ื•ึทื”ึฒืจึตื™ ื ึดื—ึทืžึฐืชึดึผื™ ื•ึผื‘ึนืฉึฐืืชึดึผื™ ื‘ึฐึผืžึทืขึฒืฉึทื‚ื™ ื•ึผืœึฐืขื•ึนืœึธื ืึตื™ื ึดื™ ื—ื•ึนื–ึตืจ ืœึฐื“ึธื‘ึธืจ ื–ึถื”

โ€œI beg You, Hashem: I have sinned before You (different classes of sins included). I have done (here one inserts the explicit sin they have committed). I regret and am embarrassed with my actions and intend to never return to those ways.โ€

Kabbalah al Haโ€™atid, Taking Upon Oneself to not Commit the Sin again in the Future

Sometimes included as a feature of azivat hacheit, this step requires one to make a resolution to better their ways. How can we do that honestly, in good faith, with our yetzer hara tirelessly and constantly lurking?

In the words of Rambam: That a sinner should abandon his sins and remove them from his thoughts, resolving in his heart, never to commit them againโ€ฆ He who knows the hidden will testify concerning him that he will never return to this sin again9. Rabbi Dovid Gottlieb explains the importance of that addition. Much as we might try, we can never be truly certain that we will no longer stumble. Who can pledge with confidence that they will never again transgress?

Rabbi Gottlieb explains that all Hashem wants is our complete commitment at the time of teshuva. If we are heartfelt in our regret, and deeply intend at that moment to try our best in the given area, we have done our duty โ€“ Hashem himself attests that we have returned completely. Only He, who searches every heart and understands every man, knows the sincerity of our resolution.  An eventual stumble does not invalidate the teshuva if one was completely earnest when doing teshuva10

Mechila

When the transgression at hand is bein adam lechaveio, between man and his fellow man, an additional step is required. One must receive forgiveness from the wronged party. In such a case, one must confess to his friend as well. 

If one is not forgiven, the halachic requirement is to try three times. In the case where oneโ€™s friend does not know of the wrongdoing, or does not know who is behind it, and there is concern the victim might be more hurt by discovering the incident, there is a leniency cited from Rav Yisrael Salanter that one should not explicitly confess11. Instead, he should ask for a general mechila for any harm or hurt he might have caused. 

Teshuva is such a dynamite power, it stands to reason that the yetzer hara will work mightily to prevent us from carving out the time, space, and focus to get it done. It is my hope that, this Elul, we all find the strength to make this beautiful mitzvah a top priority, and that come Rosh Hashanah, Klal Yisrael may stand pristine before Hashem and merit a year of absolute bounty and salvation.

  1. By different counts, there are three, four, or five steps identified. Our count in the broader one, with all possible inclusions. โ†ฉ๏ธŽ
  2. Yeshaya 55:7 โ†ฉ๏ธŽ
  3. Mishneh Torah, Teshuva 2:3 โ†ฉ๏ธŽ
  4. Song by Frank Sinatra, English lyrics by David Bowie โ†ฉ๏ธŽ
  5. Mishneh Torah, Teshuva 1:1 โ†ฉ๏ธŽ
  6. Bamidbar 5:6 โ†ฉ๏ธŽ
  7. Mishneh Torah, Teshuva 2:6 โ†ฉ๏ธŽ
  8. Mishneh Torah, Teshuva 1:1 โ†ฉ๏ธŽ
  9. Mishneh Torah 2:2 โ†ฉ๏ธŽ
  10. Rabbi Dr Dovid Gottlieb, Hilchos Teshuva part 1 โ†ฉ๏ธŽ
  11. R Binyomin Zilber, Az Nidberu 7:66 โ†ฉ๏ธŽ