He was only 30 when his natural administrational abilities landed him the appointment of prefect of the city of Rome, a position bearing responsibility for the finances, food, and defense of the city. This was at a time when the invasion of the Lombards in other parts of Italy was causing a stream of refugees to descend on Rome.
Gregory had only occupied this position for a short time when his father died, enabling Gregory to refocus the direction of his life and to respond to the grace of conversion, which he said he had long postponed.
He left public office and turned his family estate on the Caelian Hill into a monastery dedicated to St. Andrew. He also founded six monasteries on lands owned by his family in Sicily in order to provide for refugee monks who had to abandon their monasteries due to the invasions of the Lombards.
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As a monk at St. Andrew’s, he applied himself to prayer, meditation on the sacred scriptures, and the study of the Latin Fathers. His initial enthusiasm for the ascetical life led to excessive fasting, producing stomach ailments that plagued Gregory the rest of his life.
Gregory was ordained a deacon by Pelagius II and sent to Constantinople as the pope’s representative at the Byzantine court (579–586 c.e.). In Constantinople, Gregory continued to live an ascetic life in the company of monks he had brought with him from St. Andrew’s.
He also came into contact with the tradition of the Eastern Fathers and with Eastern monasticism and made important political and ecclesiastical contacts. At the suggestion of his monks, he began to give them a series of conferences of the book of Job, which would become his longest work, the celebrated Moralia.
Returning to Rome, Gregory continued to advise the pope, now as one of the famed seven deacons of the city. During a plague that devastated the city, Gregory threw himself into aiding the stricken populace, organizing penitential processions and raising the spirits of the city.
When Pelagius II succumbed to the plague, both the clergy and the people acclaimed Gregory pope. As the first monk to accede to the chair of Peter, Gregory’s early letters as bishop of Rome testify to his struggle to reconcile an active life with his deepest desires for a life of contemplation.
In reconciling these two vocations in his own life, he would insist on the need for every Christian, religious or lay, to practice the vita mixta, to balance the spiritual life with both works of charity and time for God alone.
He would also draw on monks to help him in active ministries, either as bishops or as missionaries, as when he sent Augustine (future bishop of Canterbury) and 40 monks from St. Andrew’s to Britain in 597 to bring the gospel to the Anglo-Saxons. Pope Gregory’s continual endeavors to help his people were complicated by the emperor’s dilatory dealings with the barbarians.
In 594 an exasperated Gregory took matters into his own hands, which—while evoking the displeasure of the emperor—resulted in saving the city from the destruction threatened by Agiluft, the Lombard king. In the wake of the civil government’s failure to take responsibility, the people would henceforth regard Gregory as their true leader and protector.
Gregory’s writings include letters, homilies, commentaries on scripture, and works specifically directed to the clergy or to the laity. His works continue to be of great value for their teachings on morality, asceticism, and mysticism. Like Augustine of Hippo, whose writings he knew well, he continually combines lofty doctrine with personal experience.
A theme that permeates all his works is the desire for God, who alone can fulfill a person’s interior emptiness. The desire results in interior peace, a peace coming from God, which means that the very desire for him is already a part of his peace.
A work designed for the common people is the Dialogues, a series of discussions with a certain Peter the deacon. They were written during a period of natural catastrophes and barbarian invasions and are meant to show that holiness—through examples of sixth-century saints—is possible even in their own chaotic times.
The second book of the Dialogues is totally given over to the life of Benedict and is the only ancient source for the life of this saint. For the clergy Gregory wrote his Pastoral Care, a work on the care of souls (the "art of arts" as he calls it) and is a guide for priests and bishops.
It places emphasis on the need for a pastor to be a man of virtue and discernment who teaches by word and example. Gregory always considered the cleric to be a man of service, as is evident in the title he used for himself: servus servorum Dei or "Servant of the servants of God", which every bishop of Rome has since adopted.
It is difficult to know what contribution, if any, the saint made to what are now called the Gregorian Sacrament (missal used at Mass) and Gregorian chant (church music in Latin), but the attributions are worthy tributes to Gregory’s endeavor to enhance the liturgy of his day. The Western church observance of his feast day is September 3.