Heaven, Hell, and the Power of Regret: What the Sages Teach About the Soul’s Journey After Death

The Midrash teaches: “God gave the Torah to Israel and made a condition with them: Whoever keeps the Torah — the Garden of Eden lies before him. Whoever does not keep the Torah — Gehinnom (the purifying fire of the soul) lies before him.” (Shemot Rabbah 2)

Rabbi Shmuel added in the Talmud: “Whoever performs one mitzvah in this world — that mitzvah goes before him and leads the way in the World to Come. But whoever commits a sin in this world — that sin wraps around him and precedes him to the Day of Judgment.” (Sotah 3b)

The Deepest Regret

Have you ever felt a piercing regret — the kind that fills the heart with unbearable sorrow, that makes you wish you could turn back time and undo a terrible mistake?

The Vilna Gaon (Rabbi Eliyahu of Vilna, 18th century) described a level of regret so intense that no living person could ever experience it: “When a person is led from his house to his grave, all his senses are opened. He sees what he could never see in life — the punishments of Gehinnom and the delights of Gan Eden. He realizes how he wasted his days on emptiness. Then he understands how many moments of eternal pleasure he lost, how every single hour could have earned him the delights of paradise — pleasures beyond human comprehension. His heart breaks with regret, and he begs God to let him return for just one more chance to study Torah and perform good deeds. He tears his hair and cries, ‘Woe to me! I traded an eternal world of light for a fleeting world of darkness.’ This sorrow, is greater than all the torments of Gehinnom.” (Cited by a disciple of the Chofetz Chaim, in Likutei Ma’amarim)

The True Nature of Heaven and Hell

The rewards of Gan Eden (Paradise) and the punishments of Gehinnom cannot be understood with earthly terms.

Foolish nations imagine “heaven” as a place of endless physical pleasure, and some even promise sensual rewards to so-called martyrs. Judaism however teaches the opposite — that spiritual joy is infinitely greater than any bodily pleasure, and that souls who corrupt themselves through violence and lust descend instead into spiritual darkness and torment.

As the Rambam (Maimonides) writes: “The ultimate good awaiting the soul in the World to Come cannot be understood or grasped in this life, for all we know here are physical pleasures. But that good is immeasurably greater — beyond description or comparison. As King David said: ‘How abundant is Your goodness which You have hidden for those who fear You’ (Tehillim 31:20). And Yeshayahu said: ‘No eye has seen, O God, but Yours, what You have prepared for those who await You’ (Yeshayahu 64:3).” (Mishneh Torah, Hilchot Teshuvah 8:1–2)

One moment of joy in the World to Come, say the Sages, surpasses all the pleasures of this world combined: “Better one hour of spiritual delight in the World to Come than all the life of this world.” (Pirkei Avot 4:16)

The Pain of the Soul

Just as the soul’s reward is spiritual, so too are its punishments. When the Torah and the Sages speak of fire, burning, or torment, these are metaphors for spiritual pain — the anguish of a soul that recognizes what it has lost.

The Midrash Kallah Rabbati tells of Rabbi Akiva encountering a blackened, soot-covered man running frantically with a load of wood on his back. The man revealed that he was not alive — he was a soul from Gehinnom, condemned to gather wood for his own burning, seven times a day, endlessly. The “fire” was not physical — it symbolized the soul’s unbearable torment and shame.

The prophet Shmuel refers to another form of punishment called Kaf HaKela — “the sling of the soul”: “The soul of your enemies He will hurl away in the hollow of the sling” (Shmuel I, 25:29) — describing the soul’s being violently cast about, unable to rest, torn between yearning for light and the weight of its sins.

The Ramban (Nachmanides), in Sha’ar HaGemul, explains that sins block the soul’s natural pull toward its divine source. The thicker and coarser a person’s misdeeds, the more they separate him from God: “The soul longs to return to its spiritual root, but the heaviness of sin prevents it. This separation causes an agony greater than any physical suffering, for it is the pain of disconnection from the Source of Life itself.”

The Weeping of Rabbi Yochanan ben Zakkai

The Talmud (Nedarim 28b) recounts a poignant moment before the death of Rabban Yochanan ben Zakkai, the great leader who saved Torah learning after the destruction of the Temple.

When his students came to visit him, they found him weeping. They said: “Light of Israel, mighty pillar, hammer of strength — why do you weep?”

He replied: “If I were being led before a human king — who lives today and dies tomorrow — even if he were angry, his anger would not last forever. Even if he imprisoned or executed me, his punishment would not be eternal. I could plead with him or bribe him. Yet I would still tremble. And now they lead me before the King of Kings, the Holy One, blessed be He — who lives forever and ever. If He is angry with me, His anger is eternal. If He imprisons me, His imprisonment is eternal. If He condemns me to death, His death is eternal. I cannot bribe Him or persuade Him. And before me lie two paths — one to Gan Eden and one to Gehinnom, and I do not know which I will be led upon. Shall I not weep?”

A Final Reflection

The words of the Sages are not intended to frighten, but to awaken.
Every moment in this life is an opportunity — to speak kindly, to give, to study, to love, to rise higher.

For when the eyes of the soul are opened, it will see — with painful clarity, that every small act of goodness could have become a doorway to eternity. And every wasted moment, a treasure lost forever.