The Monks Symeon and John were Syrians, and they lived in the sixth century at the city of Edessa. From childhood they were bound by close ties of friendship. When Symeon was thirty years old, and John twenty-four, they made a pilgrimage to Jerusalem on the Feast of the Exaltation of the Cross of the Lord. On the journey home the friends spoke of the soul’s path to salvation.

Passing through Jordan, they saw monasteries on the edge of the desert. Both of them were filled with an irrepressible desire to leave the world and spend their remaining life in monastic struggles. They were tonsured monks by the Abbot Nikon, and soon after left the monastery with the Abbot's blessing to struggle together in the wilderness near the Dead Sea.

When they began their life in the desert, the spiritual brothers at first experienced the strong assaults of the devil. They were tempted by grief over abandoning their families, and the demons tried to discourage the ascetics, subjecting them to weakness, despondency and idleness. They spent their time in unceasing prayer and strict fasting, encouraging one another in their struggle against temptation.

After a while, with God’s help, the temptations stopped. After this Symeon and John lived in the desert for twenty-nine years, and they attained complete dispassion and a high degree of spirituality. Saint Symeon, through the inspiration of God, considered that now it was proper for him to serve people. To do this, he must leave the desert solitude and go into the world. Saint John, however, believing that he had not attained such a degree of dispassion as his companion, decided not to leave the wilderness.

The brethren parted with tears. Saint Symeon chose for himself the difficult task of foolishness for Christ. Having come to the city of Emesa, he stayed there and passed himself off as a simpleton, behaving strangely, for which he was subjected to insults, abuse and beatings. In spite of this, he accomplished many good deeds. He cast out demons, healed the sick, delivered people from immanent death, brought the unbelieving to faith, and sinners to repentance.

Saint John highly esteemed his spiritual brother. When one of the inhabitants of the city of Emesa visited him in the wilderness, asking for his advice and prayers, he would invariably direct them to “the fool Symeon”, who was better able to offer them spiritual counsel. For three days before his death Saint Symeon enclosed himself in his hut, where there was nothing except for bundles of firewood. Having remained in unceasing prayer for three days, Saint Symeon fell asleep in the Lord. Some of the city poor, his companions, had not seen the fool for some time. They went to his hut and found him dead.

Taking up the dead body, they carried him without church singing to a place where the homeless and strangers were buried. While they carried the body of Saint Symeon, several of the inhabitants heard a wondrous church singing, but could not understand from whence it came. After Saint Symeon died, Saint John also fell asleep in the Lord.