Yefashpeish b’Ma’asav (Responding to Difficulties & Challenges) — Part 1  

We all know that yissurim (difficulties and challenges) are a part of life. What we may not realize, however, is that they are a necessary part of life. In fact, the Gemara Arachin (16b) says that if forty days would go by without one having any yissurim at all, it would be considered a terrible tragedy — as if he had been abandoned, G-d forbid. We are used to thinking about yissurim mostly in terms of their perceived justice or injustice, as in the classical theological and philosophical question — “Why do bad things happen to good people?” As important as that question is to ask and try to understand, there is another question which may be just as important, or perhaps even more important, to ask — “What is the proper way for us to respond to the yissurim in our lives?” 

How should we respond to yissurim?

The Gemara Brachot (5a) presents a sequence of three different responses to yissurim: 

If one sees yissurim coming upon him, [first] yefashpeish b’ma’asav (he should examine his actions)… 

[If he] should examine [his actions] but didn’t find [a cause of the yissurim], he should assume it was because of bitul Torah (neglect of Torah learning — i.e., not having worked hard enough to grow)… And if he thought [that it might be because of bitul Torah] but [also] didn’t find [the cause], then they must be yissurim shel ahavah (afflictions of love).

The Maharsha (Brachot 5a) asks an obvious question on this sequence: 

How would it be possible for anyone to examine his actions and not find that he had done anything wrong? After all, there is an explicit verse which tells us — “There is no tzadik (righteous person) in the world who does only good and never transgresses” (Kohelet 7:20).

Rashi (Brachot 5a) explains that “examining but not finding” is referring to an aveirah (transgression) for which these yissurim would be a fitting outcome. While no one can say they found no aveirot (transgressions) at all, it may simply be that they found none that seemed likely to have brought about these particular yissurim.  

The Gemara Brachot (5a) speaks about a sequence of yissurim leading to yefashpeish b’ma’asav (examining one’s actions), and then doing teshuva (spiritual return). The Gemara did not say that the yissurim should cause one to go straight to teshuva. 

The Mabit (Beit Elokim) explains: 

This is because one needs to know and to recognize that these yissurim came upon him properly and appropriately as a result of the aveirot which corresponded to them.

Often, our first thought is to complain when difficulties befall us, as opposed to thinking what we ourselves may have done to cause them. 

It is, therefore, appropriate for us to examine our ways and to search for which aveirot could have brought about this difficulty. We know that, in general, we have aveirot, and this is something we can’t evade. After all, as the possuk (verse) tells us — “There is no tzadik in the world who does only good and never transgresses” (Kohelet 7:20). We don’t need any investigation or examination for that! Therefore, it seems that the examination is needed to identify which specific aveirah brought about these yissurim. Once one knows this, he will then be able to do teshuva for this particular aveirah, since the teshuva varies according to the aveirah.

The Iyun Yaakov (Brachot 5a) cautions that one should not relate to physical yissurim as chance occurrences, and simply go right away to a doctor for a physical cure. Rather, one should first examine his actions, and also learn mussar (ethical teachings). Just as a doctor needs to search out the origin of illnesses, similarly with spiritual health, one must examine his actions [to see] which aveirot [caused] these yissurim to come upon him. He will then be able to do a teshuva which addresses these specific things, which is really the essence of a spiritual cure. 

The Gemara Brachot continues (5b) with a story of Rav Huna who had 400 barrels of wine which turned into vinegar. The Rabbis who came to visit him told him to examine his actions. He asked them, “Am I really suspect in your eyes to have done something that could have caused this financial loss?” They replied, “Is G-d suspect in your eyes to have given you a judgment that you didn’t deserve?” He then asked them if any of his behavior seemed to be suspicious. They pointed out that he had recently withheld giving something to a person who had once stolen from him. Even though that person had been a thief, Rav Huna accepted upon himself to give this thief the full amount he had withheld until now. And once Rav Huna committed to do that, he recovered the full amount which he had lost when the wine had soured.

The Gemara Eiruvin 13b-14b says that for two and a half years Beit Shammai argued with Beit Hillel about whether it would have been better for mankind to have been created or not. They concluded that it really would have been better for mankind not to have been created, but now that people have been created — yefashpeish b’ma’asav (we should examine our deeds). And some say — yemashmeish b’ma’asav (we should probe our deeds). 

The Da’at Chachmah u’Mussar (#22) explains that the central issue in this debate was the great danger of physicality, which can destroy the value of any action it becomes mixed into, even that of a mitzvah. The Rabbis, therefore, concluded that — “It would have been better for mankind not to have been created” — because they realized it would be virtually impossible for our actions to always be completely pure, without any trace of physicality. Once we were created, however, what is now our main task? “Yefashpeish b’ma’asav (to examine our actions)” — to refine and to purify all of our actions as much as we can.

The Sefer Kol Bo (#118 — Din Ma’aseh Torah) tells us: 

Three times every day a proclamation [from Heaven] goes out and says — While it really would have been better for mankind not to have been created [because of their potential to cause damage in the world], now that they have been created, yefashpeish b’ma’asav (they need to examine their deeds).

Yefashpeish (we should examine our deeds) is relevant to the past, since that is how we are supposed to respond to yissurim that have come upon us. 

We should examine the actions which we already did and do teshuva for our transgressions. (Ritvah and Rashi — Eiruvin 13b, Ma’or v’Shemesh — Vayishlach) 

Yemashmeish (we should probe our deeds), however, is relevant to the future — from this point forward, to try to be careful and precise with all of our actions. And we should remain continually aware of them, as it says — “A person is obligated to constantly check (yimashmeish) his tefillin,” and — “A person is obligated to check (yemashmeish) his garments every erev Shabbat.”  

We should examine the actions which we are currently doing and consider the long-term benefits and losses. (Ritvah and Rashi – Eiruvin 13b, Ma’or v’Shemesh – Vayishlach) 

Some explain that “yefashpeish b’ma’asav” means to examine our transgressions, while “yemashmeish b’ma’asav” means to examine even our mitzvot, and then to eliminate any negative aspects to make them more pure. (Eitz Yosef — Eiruvin 13b)

The Kedushat Levi (V’etchanan) explains the Gemara Eruvin in light of the Kabalah (mystical teachings): 

“It would really be better not to have been created than created — i.e., not to have needed to come back as a gilgul (reincarnation). But now that we have been created [i.e., come back as a gilgul], yefashpeish b’ma’asav, so our actions will be repaired and we will not need to come back again as [another] gilgul.    

There are many different meanings and benefits to yefashpeish b’ma’asav

The process of yefashpeish b’ma’asav for yissurim should be through middah k’neged middah (measure for measure). This will not merely repair the past, it will also be able to enhance the future, so that we will not return to our foolishness or continue with our flawed path. (Kom’miyut l’Artzeinu — Ma’amar #18)

Rav Simcha Zissel of Kelm (Ma’amar # 45) says: 

It is known that the early doctors used their experience to understand the nature of disease. Through this awareness, they understood how to protect people from illness, and how to treat people once they became sick… From this we can understand the importance of knowing the processes of spiritual afflictions as well… Therefore, the Gemara Brachot (5a) tells us — “If one sees yissurim coming upon him — yefashpeish b’ma’asav”… There is, therefore, an obligation to [try to] understand these matters through middah k’neged middah, although it is an extremely difficult task.   

The Mishnah in Pirkei Avot (4:13) says: 

“Teshuva u’ma’asim tovim (good deeds) are like a shield against difficulties” — Just like a shield requires awareness for it to be placed properly against the incoming arrows, and if not, it won’t be able to protect, similarly teshuva requires “yefashpeish b’ma’asav” — that one examine their deeds and then repair whatever is crooked. (Ahavah B’Ta’anugim) 

Yefashpeish b’ma’asav is the actual purpose of the yissurim. G-d established the system of middah k’neged middah (measure for measure) so that if a person strays from the true path, he will receive yissurim that correspond, and will then be able to find his error. We see this in the story with Rav Huna whose wine became vinegar. (Chachmah u’Mussar #79 and 222) 

In contrast to the Gemara Brachot (5a), which speaks about yissurim leading to yefashpeish b’ma’asav (i.e., seeing what we did wrong), the Zohar (2:167) says that the purpose of yissurim is not only to remind us to examine our deeds, but also to identify our internal flaws, in order to then be able to serve Hashem properly. The Zohar outlined the two basic choices every person faces — the “path of life,” and its opposite. The identifying feature of what it called the “path of life” is that it contains tochachat mussar — guidelines for self-improvement. When Hashem wants to guard this path of life, He establishes these rebukes and makes tochachat mussar for the people of the world. 

The Arvei Nachal refers to this explanation of the Zohar (2:167), as opposed to the simple understanding of the Gemara Brachot (5a) alone. While the Gemara viewed transgressions as the primary cause of the yissurim, the Zohar understood that yissurim should awaken us to the proper path in life through identifying our negative traits.       

Every person has aspects of perfection and areas where he is lacking. Our essential work is to address what we are lacking. These lacks will only be considered failings, however, if we don’t attempt to rectify them. If we do strive to correct them, they will end up being viewed as our essential work in life. Part of this work is not merely to strengthen ourselves in our areas of weakness, but even to use these very weaknesses to complete ourselves. The Chovot HaLevavot (Avodat HaElokim, chapter 10) writes that no negative traits were created in vain…we should even try to use them to serve Hashem.  

The Tur (#204) explains that the main purpose of aveilut (mourning) is to be yefashpeish b’ma’asav, and to [then] return in teshuva. (Yabiah Omer #7 — Yoreh Deah #29)  

 Torah wants us to view yissurim positively and with justice 

The Meiri writes: 

Among the foundations of our religion is for a person to contemplate and to recognize that everything which occurs to him, with all types of difficulty, is proper and with justice. As the Rabbis (Chulin 7b) teach — “No person even stubs his toe below unless it was decreed upon him from Above.” This will then lead him to examine his deeds, and to return from his bad path… Whether in one’s possessions or with people, one should always suspect himself more than suspecting the justice of Hashem. (Chulin 7b, Brachot 5a)   

The Sefer HaChinuch (Mitzvah #169) adds, when discussing the tumah of the metzora: 

Since we need to establish in our souls that Hashem supervises every single person, and that His eyes are watching all of our ways, we are warned to pay attention to every illness and to realize that a transgression caused it. And this will lead us to be yefashpeish b’ma’asav.

The Torat Avraham writes that, in place of nevuah (prophesy) today, Hashem has given us yissurim: 

Yissurim are not a punishment for aveirot of the past, but rather teachings and guidance to avoid [more] transgressions in the future. As the Gemara Brachot (5a) says — “If one sees yissurim coming upon him — yefashpeish b’ma’asav.” And according to how sensitive we are to the yissurim, the greater will be the revelation of the personal “nevuah” that they give us.

The method of our investigation will be, as our Sages have explained, through the approach of middah k’neged middah (measure for measure), to find the aveirah that would logically have caused these yissurim to come upon us. When Hashem sends yissurim to wake us up to teshuva, a person is able to realize what the issue is by analyzing the type of yissurim that he is dealing with. Similarly, Rav Chaim of Volozhin explained in Ruach Chaim (on Pirkei Avot 4:11) — “Teshuva and good deeds are a shield against difficulties” — Just like a shield protects only when it is held in front of the specific limb which the arrow is targeting, teshuva is exactly the same way. If yissurim are coming to a person on a specific limb, one needs to improve the actions associated with that specific part of the body. Teshuva will help to remove yissurim only if one is successful in fixing whatever was wrong with that part of the body which the yissurim were poised to hit. 

Even mild yissurim can help to rectify our transgressions 

The Madregat HaAdam (u’Bacharta b’Chaim — chapter 1,2) points out: 

The degree of yissurim that people need will often be unclear to them. How can they know what level of yissurim are necessary to rectify a particular aveirah? [In fact,] even a slight inconvenience or something that could easily be ignored could be considered as yissurim that will be able to rectify aveirot. While people often forget the small difficulties because of the big ones, they are all considered and calculated by G-d.          

Just like small yissurim which are ignored by most people are still called yissurim, and are able to rectify aveirot — bigger yissurim, which great people may even view positively, will also be called yissurim, and will also be able to rectify their aveirot. These great people should certainly not lose the cleansing power of their yissurim simply because their elevation allowed them to view these yissurim positively. 

After all, what made the yissurim easier for them to accept was not that they were not painful for them, but rather that they were capable of dealing with this pain. They will, therefore, not only gain from the cleansing of the yissurim, they will also end up even more elevated from this ability to accept their yissurim properly. Just like G-d decrees the yissurim which are given to people, He also gives every person the choice of how they will deal with the yissurim which they have been given…yissurim come upon us not only to cleanse us from our aveirot, but also to elevate us. Only one who strengthens himself in the face of yissurim will achieve both benefits. One who does not strengthen himself will not be elevated by yissurim, but he will still gain from the rectification of his aveirot.  

Rav Avigdor Miller explains:

Yissurim bring a person to recognize the Creator of the world, which is a merit for him. Along with this being a great merit, it can also be a difficult test. There are, however, minor yissurim which are [also] relevant to each and every one of us. [In fact,] one who goes 40 days without even minor yissurim is considered to have “acquired this temporal world” (Gemara Arachin 16b) [and thereby lost any connection to the eternal world to come.] There is no greater tragedy than this! Day by day [with no yissurim at all to wake him up] the barriers which separate him from his Creator will grow stronger and stronger. Therefore, the Rabbis have come and given us great and beneficial advice. Even minor things that commonly occur to people every day are also called “yissurim.” We simply need to pay attention to them and to accept them as “yissurim.” 

Whoever does this will gain two benefits from these yissurim: 

First, is the recognition that there is a Creator of the world that is guiding His world, and He is the One bringing the yissurim on him. 

Secondly, by seeing that yissurim have come upon him, he will then yefashpeish b’ma’asav, examine his actions. 

If we use the small things that occur to us, like the examples the Rabbis give us [in Gemara Arachin 16b], and we then attain the benefit from these occurrences, we may thereby be able to avoid more difficult yissurim. There will be no need to bring them upon us since we will have already learned and acquired yirat Shamayim (fear or awe of Heaven) from these small things. (Torat Avigdor) 

In the desert, Hashem both afflicted the Jews and healed them, He withheld food from them while sending them the manna. We need to realize that when Hashem sends yissurim, it is not to take revenge, but rather for our own good, because of the love which He has for us. He wants to return us to the good so we will then go in the good path.

Thus Hashem says to the Jewish people — “Don’t think that I am relating to you like slaves. If a person sees that his slave is not behaving as he would like, he tries to sell him. Rather, I am bringing yissurim upon you in order to get you to do teshuva, since I swore that I would never abandon you.” Therefore, the Gemara teaches — “If one sees yissurim coming upon him — yefashpeish b’ma’asav.” Perhaps he did an aveirah that caused these yissurim, and he should try to do teshuva, so that the yissurim will cleanse him of the aveirah… While yissurim may be bad for the body, they are good for the neshama (soul)… 

And just like a parent doesn’t afflict a child [fully in] accordance with what the child did, but rather somewhat less than what is deserved, similarly Hashem afflicts us in Olam Ha’zeh (this world), and not [fully in] accordance with what we did [which would be given in Olam Haba (the world to come)]… Any pain which a person endures in this world can be considered to be yissurim, even very minor pain; they are all able to minimize his aveirot, so he can then inherit Olam Haba. (Yalkut Me’am Lo’ez — Devarim 8:5) 

Yefashpeish b’Ma’asav means to make thinking and learning a fixed and consistent part of our lives

Learning Torah

The second response of the Gemara Brachot (5a) is that, if one did not find an aveirah which fit, the yissurim were caused by bitul Torah (neglect of Torah learning). 

Rashi (plus the Eitz Yosef — Eiruvin 13b) explains that this is because yissurim should bring a person to Talmud Torah (learning of Torah). 

The difference between the illnesses of the body and the illnesses of the soul is that with physical illnesses, the success of the cure does not require the sick person to understand his sickness. Even if he doesn’t understand it at all, the doctor can still heal him. This is the opposite with spiritual ailments, the very source of which is the person’s lack of awareness of his evil. [In fact,] every [spiritual] problem is essentially a mistaken path which seems proper in one’s eyes. (K’nesset Yisrael — Ohel Yaakov on Tehillim 32:3)

Learning Mussar

If one doesn’t learn mussar (life lessons) for himself from all situations, the Rabbis call him a “rasha” (evil person). Even if he is presently a tzadik (righteous individual) and gadol hador (the greatest of the generation) who has not yet transgressed, he still needs to take mussar for himself… All the more so, one who has not yet reached a high level before transgressing certainly needs to take mussar from every situation. (M’vakshei HaShlamot — Shelach)  

Rav Aaron Kotler (Mishnat Rebbe Aharon — Elul — Chovat HaHitbon’nut v’Limud HaMussar) writes: 

The essence of mussar is to afflict oneself, as it says (Gemara Brachot 7a) — “One aspect of self-discipline in one’s heart is better than 100 lashes.” The Gra explains in a letter — “One must constantly afflict oneself, but not with fasts or physical afflictions, rather with restraining one’s mouth and one’s desires, and the like.” Mussar should be in place of yissurim since it will make us regret…our confusions.  

Thinking and Introspecting

Rav Simcha Zissel of Kelm says: 

The yissurim which G-d brings upon us, as well as those of the world, are all for the good — to awaken us to improve. This is only true, however, when we examine our actions in terms of middah k’neged middah. We will then gain in two different ways — we will be cleansed [in terms of the past], and we will be inspired for the future.

But if, G-d forbid, one doesn’t do teshuva, then his culpability will grow, and cause yissurim to come upon him in which he will not be able to examine his actions through middah k’neged middah — since the yissurim hadn’t helped him [until now] to rectify his aveirot. 

This was the meaning of Hashem hardening the heart of Pharaoh — in other words, his punishment was that he didn’t have middah k’neged middah revealed to him… Therefore, it is an obligation for us to strengthen our mitzvah to think. (Ma’amar # 282)

In a letter to a student of his, Rav Simcha Zissel writes: 

My heart is pained over the yissurim that you are dealing with. May you not need to suffer any more. I am happy, however, that you have asked what could be the cause, as the Gemara Brachot (5a) says — “If one sees yissurim coming upon him — yefashpeish b’ma’asav.” And this should cause you to have good health all the days of your life. How wonderful it would be if you remembered this always, and you would do teshuva your entire life. As I saw from an elder — “What hope is there for a person if he doesn’t do more tomorrow than he did yesterday.”

When I saw this, I thought — Who will be able to attain a great level like this? However, we see with children that there is no day in which they haven’t grown more than the previous day. Even if we can’t always see this with our eyes as it is happening, we know that it must be true, since we see over the course of time that they have grown. And the growth of the body is only until about age twenty, but the seichel (intellect) continues growing as long as we keep using it. However, one who doesn’t utilize his seichel and grow through it every single day, ultimately destroys it. (Ma’amar # 408)     

The sefer Da’at Chachmah u’Mussar (#9,10) explains:

Based on the Ramban, we see that even the loftiest ideas can be attained from within ourselves. We even find this in the Gemara Brachot (5a) — “If one sees yissurim coming upon him —yefashpeish b’ma’asav.” While we might have thought that this clarity of our actions could be acquired only though Torah, we see that it can also be attained simply through thinking. The brothers of Yosef, for example, gained clarity of hashgacha pratit (Divine personal supervision) through examining their actions in the midst of their yissurim. Even Pharaoh, who was afflicted with boils after taking Sara captive, realized that Sara must have been Avraham’s wife. He came to this realization after self-examination, which was prompted by yissurim. [Therefore, we see, that thinking and yefashpeish b’ma’asav (self-examination) resulting from yissurim can themselves lead us to a very great degree of clarity.]

The Migdanot Eliezer (Toldot) writes: 

When yissurim befall a tzadik, he will be certain that Hashem is righteous. He will, therefore, accept the din (judgment) upon himself, since he knows that nothing is random. At the same time he will not fall into depression, but rather will control himself and straighten whatever had been twisted. Evil people [may] also not worry about their transgressions or fall into depression. To an onlooker, they may appear to be having the same reaction. There will, however, be an enormous distinction between the two of them. The tzadik knows that he transgressed, but in order to maintain his service of Hashem, he forces himself to continue serving Hashem with simcha. The rasha, however, doesn’t think about his aveirot because they don’t matter to him. He doesn’t even see himself as having transgressed, since he feels that whatever he did was permissible.

The proof of this is that when yissurim come upon them, the tzadik will examine his actions, while the rasha views it all as randomness, never imagining it as the result of his aveirot. Therefore, middah k’neged middah, G-d then makes the yissurim look random [to the rasha], thus making it very difficult for him to be able to do teshuva. 

Rabeinu Bachya (Kad HaKemach — Eivel #3), in his explanation of aveilut (mourning), explains:

It is fitting to be yefashpeish b’ma’asav…and to contemplate the day of death. One who doesn’t consider the day of death is likened by the verse to an animal that is destined for shechita (slaughter). The end of man is death, and the end of an animal is shechita, but the animal doesn’t feel the day of his death until the time when it is brought to be slaughtered. Similarly, there are people who, like animals, don’t think at all about the day of death until they actually arrive there. 

Cheshbon HaNefesh (Spiritual Accounting)

The Mesillat Yesharim (chap. 2,3) writes about the critical importance of a regular cheshbon hanefesh (spiritual accounting or examination):  

Chapter 2: 

Zrizut (vigilance) relates to a person’s actions and matters. They must contemplate, examine, and survey their actions and conduct, to see whether or not they are good… 

And they must not go [through life] haphazardly, as a blind person walks in darkness. 

This is certainly something that our logic demands. Could it be that a person with knowledge and understanding to save himself…should want to close his eyes to his own salvation? Nothing is as base and as foolish as this. One who does this is lower than the animals and the creatures that naturally protect themselves, fleeing and escaping from what they see could harm them. One who walks without thinking whether his path is good is like a blind man walking along a riverbank. He is in great danger. 

The prophet Yirmeyahu [characterized people doing this] — “… like a horse charging straight into battle.” In other words, they were racing forward impulsively with no time to evaluate their conduct. They, therefore, fell into evil without any real awareness…

This is one of the main strategies of the yetzer hara (evil inclination), which constantly works to burden people’s hearts until they are left with no time either to think or to observe their path. It knows that if they would pay attention only minimally to their ways, they would immediately begin to regret their deeds, and would eventually abandon transgressions entirely.

If one oversees himself, G-d will help him to be saved from the yetzer hara. But if he does not, then G-d will certainly not watch over him. For if one is not compassionate [toward himself], who else will show him compassion? 

Chapter 3: 

One who wishes to oversee his conduct…must consider what constitutes the true good which a person should choose, and the true evil from which he should flee.

The Rabbis referred to this when they said (Eruvin 13b): “It would really have been better for mankind not to have been created…but now that he has been created, he should yefashpeish b’ma’asav — examine his deeds, while others say yemashmeish b’ma’asav —  he should probe or feel his deeds.” 

Yefashpeish (examination) of one’s deeds means to investigate one’s actions to determine whether there are any actions among them that should not be done. 

Yemashmeish (probing or feeling), however, means to investigate even one’s good deeds; perhaps they contain some — even partly — negative aspect which one must eliminate. This is like feeling a garment to see if it is good and strong, or weak and frayed. Similarly, one must examine his deeds thoroughly to determine their nature, until he becomes pure. 

It is also necessary that one be careful in his ways and evaluate them daily, like the merchants do to prevent their businesses from falling into ruin. One should make fixed times for this, rather than doing it haphazardly, and stick with these times, because the results are so great. 

The Rabbis explicitly taught us the need for a cheshbon hanefesh – “to calculate the loss of a mitzvah versus its gain, and the gain of a transgression versus its loss…” (Pirkei Avot 2:1). They have already experienced this and seen that this alone is the true way for man to attain the goodness that he seeks. 

The Chovot HaLevavot also discusses the importance of cheshbon hanefesh (this spiritual accounting):

Cheshbon hanefesh is one’s effort in terms of both Torah and worldly issues to understand which of his obligations he has already fulfilled, and what he still needs to do. (Chap. 1)

This effort with both Torah and worldly issues will differ in terms of one’s perception, intelligence, and clarity of understanding. Every single person is obligated to calculate what he is required to do to serve his Creator, according to his recognition of the good of his Creator — both in general and for him specifically. (Chap. 2)

The benefit of this calculation will directly impact the soul… As a result of this, one will acquire all virtues and attain all precious qualities. (Chap. 4)

One is obligated to do this cheshbon constantly, according to his intellectual ability and his degree of recognition, at all times, and with every single breath he takes. (Chap. 5) 

Based on the responsa of the Mareh Yechezkial (104 – #151 “HaGadol MiMinsk”) we see:

When the Rabbis tell us that the proper response to yissurim or any type of difficulty is to be yefashpeish b’ma’asav, this means that we need to study works like the Chovot HaLevavot on cheshbon hanefesh, even when it is neither [the month of] Elul nor the ten days of teshuva. There is no greater examination of one’s deeds than studying works like this, which dissect the various confusions of people down to their fine details. When we come to an example in which we had stumbled previously, we will then remember and be on our guard. Our intention with this should not merely be to understand proper behaviors and to learn lofty ideas and then analyze them like we do with our other learning, but rather to understand the simple meaning of the words, and to really incorporate them into our lives. 

The Sefer Kol Bo (#67 — Din Seder Darchei HaTeshuva) presents a very demanding cheshbon hanefesh regimen to maintain vigilance in one’s life:   

To guard yourself from all transgressions, when you first get up in the morning, think lofty thoughts, yefashpeish b’ma’asav, and try not to deviate at all until breakfast. If you did deviate in any way before breakfast, you should recite viduy (verbalize to G-d) over it immediately, to distance yourself from any further transgressions. If some other transgression then presents itself before you, distance yourself from it by saying — “How could I do this great evil, to recite viduy over something, and then return to do it again?” 

If, when you got to breakfast, you were yefashpeish and didn’t find anything wrong, you should thank and praise your Creator for helping you merit to do teshuva shleima (complete teshuva). And just like you made it from the morning until now [without transgressing], you should also work to guard yourself from now until dinner time. 

Before you eat dinner, you should repeat this process, and similarly from dinner time until you go to sleep. You should repeat this process — of these three daily time periods — every single day, for a month or a year, until you have established and strengthened the service of your Creator, and abandoned all evil deeds… You should then feel secure and no longer afraid since you will be helped from Heaven. And your past transgressions will now be considered like merits.  

The Hanhagat Tzadikim teaches that we need to remember, every single night:

This world is not where we really live, since the way of the world is that we will eventually die. In addition, we should be concerned that we may die suddenly. Therefore, every night we should examine out actions in terms of what we did today, and really pay attention to what occurred. 

The Shelah HaKadosh writes that, as part of the regular preparations for Shabbat, one should examine his actions and do teshuva to fix whatever needs repair. Only then should one cut his nails and go to immerse in a mikvah, like a woman who is purifying herself, since there is no tumah (spiritual lacking) like the tumah of aveirot. 

Continued in part 2