The Right Time: When Should One Repent?

The Mishnah states (Yoma 8:9): "For one who says, 'I will sin and repent, sin and repent,' no opportunity is given to repent." As soon as a person feels inspired to repent, they should do so without delay. If they say to themselves that they can continue sinning and only repent later, they might miss their chance, as "no opportunity is given to repent."

The Sages offer a beautiful parable about a person who wants to continue wallowing in sin and only repent afterward:

A parable of a man sitting at his table loaded with all kinds of food, hungry and eager to eat. While he was eating, a poor man arrived at his door asking for food, but the man turned away and gave him nothing, and the poor man left disappointed. After an hour, they brought him more food, but his stomach was already completely full. Seeing that he could not eat anymore, he said: "Give this food to the poor man!" A wise man standing beside him said: "Fool, if you could still eat, you would give him nothing. Only now, when you have no strength to eat more, do you give it to the poor man"...?!

This is like a person in this world, going about in vanity, hungry to eat and gain wealth and pleasures. The poor man, who represents the good inclination, comes and asks him to please repent, study Torah, and fulfill commandments. But the person refuses because he is hungrier for wealth and worldly pleasures. Later, they catch him by the collar. When he sees that he can no longer gain more [when he has already aged], he says: I will repent. Perhaps they will give him the opportunity, or perhaps not. Hashem says to him: Fool, now that you can no longer gain more, you say you will repent?! If you were still able to gain more, you would not have repented! While in this state, his soul departed. This is what the verse says (Ecclesiastes 12:1): "Remember your Creator in the days of your youth, before the evil days come and the years arrive when you will say, 'I have no pleasure in them.'" (Midrash HaNe'elam Lech Lecha)

In fact, a person who wants to continue sinning and only repent later shows that their repentance is not sincere and genuine, because if they truly wanted to repent, they would not be able to continue sinning.

Besides this, the Mishnah emphasizes another point on this matter:

The Mishnah says: "... And repent one day before your death" (Avot 2:10) - repent the day before you die. The obvious question is: Does a person know when they will die? Is the Mishnah suggesting that one should repent only in old age? Certainly not. Rather, the Mishnah comes to open our eyes: You don't know the day of your death! So, better one hour sooner! Repent today, for you may die tomorrow!

Rabbi Elimelech of Lizhensk was accustomed every Friday to walk with his son to the cemetery, and would say to him: "See all these graves, consider how much they would desire and rejoice if they were given just one more hour to live and make amends. But they no longer can, and a person does not know their time, so better one hour sooner."

How Can We Not Be Prepared?!

Rabbeinu Bachya says: If someone were to warn the people of a town saying, "People, be prepared to journey to the World to Come, because one of you will pass away this month," without telling them who it would be - wouldn't each person be prudent to prepare for death, fearing they might be that person?! How can we not all be prepared, when we see that death takes a large number of the living every month. Shouldn't we fear for our souls and consider our affairs, our provisions, and our eternal home - before the time when we will need them!" (Chovot HaLevavot, Gate of Repentance)

Serve Hashem with Joy!

The Gemara states (Berachot 5a): "A person should always provoke the good inclination against the evil inclination [as it says (Psalms 4:5): 'Tremble and do not sin']. If he succeeds - good; if not - he should engage in Torah study [as it says: 'Commune with your heart']. If he succeeds - good; if not - he should recite the Shema [as it says: 'Upon your bed']. If he succeeds - good; if not - he should remind himself of the day of death [as it says: 'Be still, Selah']."

In other words, there is a gradual therapeutic treatment against the evil inclination: If a person faces a test and the evil inclination tempts them to sin, they should first "provoke" the good inclination to go to battle. If this works - good; if not - they should engage in Torah study. If this works - good; if not - they should recite the Shema, accepting the yoke of Heaven. And if even this doesn't help - they should remind themselves of the day of death.

We see, then, that remembering the day of death is the strongest and most effective remedy. However, if so, why didn't the Sages advise using this remedy immediately? Why start with other remedies that may or may not help? This is similar to a doctor prescribing medication: first, they give milder medications, and only if those don't help do they prescribe a stronger one. This is because the stronger medication is not pleasant at all and has unwanted side effects. The same applies here - first, one should overcome the evil inclination through positive means - mobilize the good inclination, the straight conscience that calls a person to obey their God. Also, one should study Torah, which is the finest antidote against the evil inclination, and recite the Shema, thereby strengthening their connection with Hashem and declaring that they accept His sovereignty and want to serve Him out of love and exaltation. But if all this doesn't help - then there is a need to employ the strongest remedy, the less pleasant, less sweet one: remembering the day of death. Remembering and visualizing the day when every person will stand before the Throne of Glory to give an account of all their actions.

This is indeed a strong and very effective remedy, but sometimes it may be accompanied by side effects of sadness and despair. Serving Hashem in this way, out of "fear of punishment," is a less desirable level of divine service, although it is sometimes necessary when the evil inclination especially attacks a person. But the more desirable service of Hashem, which one should persist in more, is through joy, love of Hashem, and accepting the yoke of His blessed kingdom upon us with a whole heart:

"Serve Hashem with joy, come before Him with singing. Know that Hashem is God – He made us, and we are His, His people and the sheep of His pasture"!