Ascending to the Divine: 20 Steps to True Repentance

In his book 'Shaarei Teshuvah', Rabbeinu Yonah of Gerona outlines twenty essential stages that guide a person who has sinned toward genuine repentance. These stages describe not a single moment of regret, but a gradual inner transformation that realigns a person with their divine purpose. What follows is a clear and accessible presentation of these paths of teshuvah.

Stage One: Regret

The first step is deep regret. A person must internalize the bitterness of distancing themselves from Hashem and recognize the consequences of that separation. As the Torah teaches, “Vengeance is Mine, and recompense” (Deuteronomy). The fleeting pleasure of sin is insignificant compared to the damage it causes to the soul.

Human beings were created with intellect and a divine soul in order to govern their desires, not be ruled by them. When a person realizes that they traded eternal value for momentary gratification, regret naturally follows. This regret reflects the recognition that sin contradicts the very purpose of creation.

Stage Two: Abandoning the Sin

True repentance requires abandoning the sinful behavior completely and resolving never to return to it. Scripture urges, “Turn back, turn back from your evil ways” (Ezekiel 33:11).

For someone accustomed to sin, the first step is to stop the behavior itself. Only afterward can regret and return take full shape, as Isaiah teaches, “Let the wicked forsake his way and the man of iniquity his thoughts, and let him return to Hashem, and He will have compassion upon him.”

Rabbeinu Yonah compares this to immersion in a mikvah while holding something impure. As long as the impure object remains, purification is impossible. Abandoning sinful thoughts and actions is discarding the impurity. Confession and prayer then complete the purification.

Desires are not meant to be crushed, but redirected. When channeled toward humility and righteousness, they become tools for spiritual elevation rather than obstacles.

Stage Three: Sorrow

Sorrow deepens regret by embedding it within the heart. A person should reflect on the pain of having damaged their relationship with the Creator. This sorrow should be profound enough to shake complacency and awaken serious reflection.

Imagine the anguish of losing everything due to one’s own actions. This contemplation helps engrain genuine remorse and reinforces the desire to change.

Stage Four: Sorrow Expressed in Action

The prophet Joel declares, “Return to Me with all your heart, with fasting, with weeping, and with mourning.” Repentance is not only internal. It finds expression through the body, particularly through the heart and the eyes, which often serve as gateways to sin and therefore become instruments of correction.

Stage Five: Concern

A repentant person develops concern and fear regarding their sins. This includes awareness that certain transgressions may require suffering for atonement. King David expressed this awareness when he said, “For my iniquity I will declare, I am troubled by my sin” (Psalms 38:18).

This concern also includes questioning whether one’s repentance has been sincere and complete. Spiritual growth is ongoing, and vigilance must remain.

Stage Six: Shame

Shame plays a critical role in repentance. A person should feel embarrassed before others for their wrongdoing, and even more so before Hashem, who sees and knows all. This awareness leads to humility and sincerity, grounding repentance in truth.

Stage Seven: Humility of the Heart

When a person truly understands the gravity of their actions, humility naturally follows. King David describes this state: “The sacrifices of Hashem are a broken spirit; a broken and contrite heart, O Hashem, You will not despise.”

The prophet Micah reinforces this inner posture by calling upon a person to walk humbly with Hashem. This humility is not weakness, but clarity.

Stage Eight: Humility in Action

Inner humility must be reflected outwardly. Gentle speech, calm behavior, and soft responses replace arrogance and harshness. The prophets teach that true strength is found in restraint and modest conduct.

Stage Nine: Breaking Physical Desire

Unchecked physical desire leads to sin. By practicing moderation even in permitted matters, a person learns self mastery. Redirecting desire toward mitzvot and spiritual pursuits transforms raw impulse into holiness.

Stage Ten: Improving Where One Has Failed

Each area of failure should become an opportunity for growth. If one sinned through improper sight, they should cultivate guarded vision. If one sinned through speech, they should increase Torah study. The very faculties once used for sin are redirected toward mitzvot.

Stage Eleven: Examining One’s Ways

As the verse states, “Let us examine our ways and test them, and let us return to Hashem.” Honest self examination allows a person to confront their actions clearly and respond with genuine repentance.

Stage Twelve: Recognizing the Severity of Each Sin

Understanding the seriousness and consequences of specific sins deepens awareness and reinforces protective boundaries. This knowledge fosters reverence and restraint.

Stage Thirteen: Treating Minor Sins Seriously

Small sins, when ignored, become habits. Proverbs warns that repeated minor failures dull moral sensitivity. A repentant person treats even small missteps with seriousness and care.

Stage Fourteen: Confession

Confession is a central pillar of teshuvah. The Torah commands, “And he shall confess that in which he has sinned” (Leviticus). Verbal acknowledgment of wrongdoing opens the door to forgiveness. This includes recognizing personal failings as well as inherited patterns of behavior.

Stage Fifteen: Prayer

Prayer gives voice to repentance. Hosea teaches, “Take words with you and return to Hashem.” Through prayer, a person seeks forgiveness and restoration, acknowledging that only Hashem can fully erase sin and revive spiritual merit.

Stage Sixteen: Repairing What Can Be Repaired

When wrongdoing affects others, spiritual repentance alone is insufficient. One must correct the harm wherever possible. True atonement between people requires tangible restitution.

Stage Seventeen: Pursuing Kindness and Truth

Acts of kindness and truth help cleanse sin. As Proverbs teaches, “Through kindness and truth, iniquity is atoned for.” Righteous behavior strengthens spiritual repair and reinforces moral clarity.

Stage Eighteen: Keeping Sins in Mind

Remembering one’s past sins fosters humility and vigilance. King David said, “For I know my transgressions, and my sin is always before me.” This remembrance guards against complacency.

Stage Nineteen: Resisting the Same Sin Again

The sages praise one who encounters the same temptation under similar circumstances and refrains. This demonstrates a deep internal transformation and closeness to Hashem.

Stage Twenty: Guiding Others Away from Sin

The final stage of repentance is helping others return from harmful paths. As Ezekiel urges, “Return from your evil ways.” Guiding others reflects responsibility, compassion, and a commitment to collective spiritual growth.

Through these twenty stages, Rabbeinu Yonah presents teshuvah not as a single act, but as a lifelong process of awareness, humility, and return.