“Regarding this the poets would say: Come to Cheshbon – let it be built and founded as the city of Sichon” (Bamidbar 21:27)
Rabbi Shmuel bar Nachman says in the name of Rabbi Yochanan, “What is meant by ‘Regarding this the poets (מושלים) would say’? The word מושליםcan also mean those who rule (מושל) their inclinations. What would they say? ‘Come to Cheshbon (חשבון).’ The word חשבון (aside from being a place) also refers to a calculation. They would say, ‘Come, let us calculate the ways of the world. Let us weigh the loss of a mitzvah against its reward, and the reward of a sin against its loss.’ The pasuk continues, ‘Let it be built and established.’ This means to say, ‘If you do this, you will be built in this world and established in the World to Come.’ The words ‘as the city (עיר) of Sichon(סיחון) ’ allude to the following: If a person makes himself like an עיר, which can also mean a donkey, who goes after a סייחה, which is a female horse, his end will be tragic, as the next pasuk states, ‘For a fire has come forth from Cheshbon, a flame from the city of Sichon’” (Bava Batra 78b).
“You shall know this day and consider it in your heart that Hashem, He is the G-d – in heaven above and on the earth below – there is none other” (Devarim 4:39)
The Chovot Halevavot (Sha’ar Cheshbon Hanefesh, Chapter 1) writes: Spiritual accounting means striving with the aid of one’s understanding to consider his religious and mundane concerns, so that he may know what he possesses and what is due from him, as the Prophet (Moshe), a”h, exhorted, when he said, “Know therefore this day, and consider it in your heart, that the L-rd, He is G-d” (Devarim 4:39). So, too, David Hamelech said, “O taste and see that the L-rd is good…” (Tehillim 34:9), further, “Know the G-d of your father and serve Him” (Divrei Hayamim I 28:9), further, “Do not be as the horse or as the mule which has no understanding” (Tehillim 32:9).
He continues (Chapter 2): The believer must make an account with his soul of his obligation to G-d, and must do so to the utmost extent of his ability and in accordance with his understanding of it. And whatever he can attain in practice he should diligently strive and labor to accomplish. Whatever he cannot carry out practically, let him accomplish in thought [by recognizing his obligation] and by yearning to accomplish it, as David said, “O, that my ways were directed to keep Your statutes” (Tehillim 119:5). He also said, “More to be desired are they than gold; than much fine gold” (ibid. 19:11). The Creator will consider this as a merit for him. He should also ensure to seek when he will be able to fulfill the duties he owes to the blessed Creator. He should not make far-fetched excuses and treat this duty lightly, nor neglect and overlook it, lest he be distressed on the great day of judgment, as it is says (Mishlei 13:13), “Who so despises a thing will be destroyed by it.”
For two and a half years, Beit Hillel and Beit Shammai contended over the following concept: Is it preferable for a person to have been created or not? Some argued yes, and some answered no. They came to the conclusion that it would have been better for man to have not been created… but now that he has been created, he should examine his deeds. Others say, “Let him investigate (feel out) his past deeds, or, as others say, let him examine his future actions” (Eiruvin 13b).
The Mesillat Yesharim (Chapter 3) states: These two versions constitute two sound, beneficial exhortations. For examination of one’s deeds refers to investigating one’s deeds in general, and determining whether they include certain actions which should not be performed, since they are not in accordance with G-d’s mitzvot and His statutes. Any such action should be completely eradicated.
Feeling, however, implies the investigation of the good actions themselves, to determine whether they involve any leaning which is not good, or any bad aspect which is necessary to remove and to eradicate. This is analogous to a person feeling a garment to determine whether its material is good and sturdy, or weak and rotted. In the same way, he must feel or investigate his actions by subjecting them to an exhaustive examination to determine their nature, so that he might remain free of any impurities.
To summarize, a man should observe all of his actions and watch over all of his ways so as not to leave himself with a bad habit or a bad trait, let alone a sin or a crime.
It concludes: I see a need for a person to carefully examine his ways and to weigh them daily in the manner of the great merchants, who constantly evaluate all of their undertakings so that they should not fail. He should set aside definite times and hours for this evaluation so that it is not an impromptu matter, but one which is conducted with the greatest regularity; for it yields rich returns.
