John Climacus - repentance

St John Climacus, also known as John of the Ladder, was, like St Anastasius, a 7th century monk of the monastery on Mount Sinai.

His reputation as an ascetic, theologian and spiritual father spread as far Pope St Gregory the Great who (according to St John's biographer) wrote to him in order to request his prayers and provided a sum of money for the hospital of Sinai where visiting pilgrims stayed.

John is best known for his Ladder of Divine Ascent. One of the major themes in the Ladder is that of compunction and repentance - something which is finds expression in the troparion for his feast:

By a flood of tears you made the desert fertile

And by your longing for God you brought forth fruits in abundance.

By the radiance of miracles you illuminated the whole universe.

O our holy Father John Climacus, pray to Christ our God to save our souls.

According to John, Adam is punished not for his original disobedience but for his non-repentance and his self-justification:

But Adam did not wish to say, "I sinned," but said rather the contrary of this and placed the blame for the transgression upon God Who created everything "very good," saying to Him, "The woman whom Thou gavest to be with me, she gave me of the tree and I ate."

And after him she also placed the blame upon the serpent, and they did not wish at all to repent and, falling down before the Lord God, beg forgiveness of Him. For this, God banished them from Paradise, as from a royal palace, to live in this world as exiles....

Moses, by way of contrast, is an example of someone who truly repents:

Nothing equals or excels God's mercies. Therefore, he who despairs is committing suicide. A sign of true repentance is the acknowledgment that we deserve all the afflictions, visible and invisible, that come upon us, and ever greater ones.

Moses, after seeing God in the bush, returned again to Egypt, that is, to darkness and to the brick-making of Pharaoh, who was symbolical of the spiritual Pharaoh. But he went back again to the bush, and not only to the bush, but also up the mountain.

Whoever has known divine vision will never despair of himself. Job became a beggar, but he became twice as rich again.

Baptism heals the sin of Adam, and repentance renews baptism:

Repentance is the renewal of baptism. Repentance is a contract with God for a second life. A penitent is a buyer of humility. Repentance is constant distrust of bodily comfort.

Repentance is self-condemning reflection, and carefree self-care. Repentance is the daughter of hope and the renunciation of despair. A penitent is an undisgraced convict.

Repentance is reconciliation with the Lord by the practice of good deeds contrary to the sins. Repentance is purification of conscience. Repentance is the voluntary endurance of all afflictions.

A penitent is the inflicter of his own punishments. Repentance is a mighty persecution of the stomach, and a striking of the soul into vigorous awareness.

Quotations from the relevant entry on Orthodox Wiki.)