Live as You Wish and Repent Later — Why Not? 5 Compelling Reasons

Why restrict ourselves now? Perhaps we can live a life without boundaries, doing as we please, and later in life, closer to old age, repent. This way, we can do whatever we want for most of our lives and also end our days as righteous individuals who merit heaven and the world to come at the resurrection. Sounds like a profitable deal, doesn't it? Well, not exactly. Where's the problem? Here are five reasons:

1. Our sages have already said regarding this idea, "If one says, 'I will sin and repent, sin and repent,' they are not granted the opportunity to repent" (Mishnah Yoma, Chapter 8, Mishnah 9).

When a person wishes to truly repent and correct their actions, they receive help from above, as stated in the Talmud, "He who comes to purify himself is assisted." They are given strength and heavenly lights, making it easier to return to repentance. In contrast, a person who premeditatedly decides to sin and later repent does not receive heavenly assistance, which makes it more difficult and challenging to succeed in repentance. They can always repent, but without heavenly support, it becomes much harder.

2. Maimonides explains in 'Laws of Repentance' that if someone tells themselves, "I will commit the sin, and then repent," their repentance is not considered genuine. This is because the repentance does not stem from a sincere intention and inner desire not to repeat the sin; instead, they plan in advance that after their 'so-called repentance,' they will sin again. The approach is "I will sin and repent, and then sin and repent again." Therefore, there is no true abandonment of the sin, which is a necessary step in repentance.
However, a person who sins and then repents out of true will and intention not to repeat the sin, even if they later fall into sin and repent again, their repentance is considered valid because their desire was genuinely to return, and they do not wish to sin. The sin burdens them, and they do not want it. Therefore, even if they fall into sin in the future, the repentance benefits them because they do it wholeheartedly, and they indeed strive not to sin, sincerely wanting to do what is right in the eyes of Hashem.

3. A person who repents in their old age actually misses out on decades in which they could have accumulated countless mitzvot and good deeds, which stand to their merit forever and constitute their share in the world to come. In the eternal world, not everyone will be on the same spiritual level; each will have a different spiritual status based on their spiritual work, the effort they made in strengthening and fulfilling mitzvot during their lifetime. Therefore, the most profitable deal is to perform as many mitzvot as possible during one's life and progress in serving Hashem.

4. When a person discovers the truth of the Torah and repents, their repentance is received with blessings, and they are assisted. In contrast, someone who knows the truth of the Torah and ignores it, deciding that sometime in the future they will repent, is viewed differently from the heavens and judged more harshly. This is because their delay in repentance expresses disregard for the Torah and Hashem's will.

5. And this is the simplest and clearest reason—no one can know when their last day on earth will be. A person can plan to change their life's course at a certain age and thereby merit the world to come, but sadly, they might end their life unexpectedly, without having completed the rectification of their soul, and the sorrow the soul will experience at that time is indescribable.

Can repentance be made for every sin? Rabbi Zamir Cohen provides an insightful short answer. Watch: