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  • Writer's pictureAugustinian Vocations

The Life of Saint Augustine: From Doubt to Certitude

Updated: Oct 21, 2022

The Augustinians have been following in the footsteps of St. Augustine for centuries... but why him?

Many men discerning religious life are often attracted to the story of St. Augustine. He was a man in constant pursuit of Truth. He was a man that had a challenging spiritual journey. He was a man of both devoted mind and heart.

Below is the full story from Fr. George P. Lawless, O.S.A., told at Villanova University on November 29, 2011. Fr. Lawless is an international scholar and interpreter of the writings of Augustine. Author of Augustine of Hippo and His Monastic Rule, Father George received his doctorate from the Angelicum, Rome.


Sixteen centuries ago, during the Easter Vigil, 24-25 April 387, a thirty-three year old Roman from the province of Numidia in North Africa was baptized by Ambrose, bishop of Milan in the north of Italy. That decision to seek baptism together with his son, Adeodatus, and his friend Alypius, was to have incalculable consequences for the Christian Churches and for all of western civilization. That convert to Catholic Christianity was Aurelius Augustine.


354-359 A.D. 354 A.D. Aurelius Augustine is born in Thagaste, North Africa (now Souk Ahras in Algeria) to Monica, a Catholic and Patricius a pagan who is a Roman offical (Curialis of Thagaste). Augustine has a brother named Navigius and a sisters, whose name is unrecorded. Thagaste, situated in the North-east highlands of Numidia, held natural habitats for lions and panthers, captured and sold for Roman amphitheater games. 359 A.D. Augustine attends elementary school in Thagaste (now Souk Ahras) and high school in Mandura (now M'daourouch, Algeria), 15 miles south of Thagaste.

370-372 A.D. 370-371 A.D. Augustine returns to Thagaste for a year, as his parents attempt to gain the means to further his education. His father, who has converted to Christianity, dies unexpectedly. A wealthy landowner helps the family send Augustine to Carthage for further studies. 371-372 A.D. As marriage between classes is strictly regulated by Roman law, Augustine, a Roman citizen, enters into a monogamous concubinage relationship with a woman of lower class status. A son, Adeodatus, is born in Carthage to Augustine and his partner.

372-376 A.D. 372-373 A.D. While in Carthage, Augustine becomes an Adherent of the Manichaean religious movement inspired by revelations received by a man who called himself Mani. Born in 216 A.D., in Babylonia, Mani was executed for his religious beliefs by Bahram I, in 277 A.D. 373 A.D. Augustine returns to Thagaste to teach rhetoric. 376 A.D. Augustine returns to Carthage to teach rhetoric.


Augustine was born November 13, 354, at Thagaste (now Souk Ahras) in modern Algeria. Situated some sixty miles inland from the Mediterranean Sea on one of three overland routes connecting the seacoast of Hippo (Modern Annaba) and Carthage, the backwater town of Thagaste featured little more than a hotel for travelers. With only an elementary school available to him in his hometown, Augustine, a serious but by no means exceptional student, attended high school at Madaura some twenty miles distant from Thagaste.

As a teenager, he associated with a group of teenagers who were called “Wreckers.” While he deplored their destruction of property, still he enjoyed their company in much the same way that he reveled in the company of other adolescent friends, when together they heedlessly stole pears from an orchard in an incident made famous from his Confessions. Augustine was no different from other boys from school, and he had an intense dislike for the study of Greek. However, the fact that he went to high school at all set him apart from many of his peers at Thagaste.

When he completed high school at fifteen years of age, Augustine returned home. As he was preparing to leave for advanced studies in philosophy and rhetoric at the end of the year, his father died. Patrick, the father of Augustine, was a man who lived all his life as a pagan and was converted to Christianity only shortly before his death. This significant loss happened at the very time that Augustine was experiencing a year of youthful idleness while his parents were scraping together enough money to advance still further their son’s education. Now widowed and with three children, Monica the mother of Augustine, was singularly fortunate to have the help of a wealthy landowner and resident of Thagaste who was willing to provide the necessary financial support for his education at Carthage, a city some 170 miles away from home.

Ancient Carthage was notorious as a sizzling frying-pan for illicit loves, so much so that the Latin word play Carthago, Carthage, and sartago cauldron, in Augustine’s Confessions prompted T.S. Eliot’s poetic version of this youthful adventure: “To Carthage I came, burning, burning, burning, burning.” Paganism had, indeed, been a powerful force at Madaura where Augustine spent his high school years and again at Carthage where he continued his formal education.

Having become the father of a son born out of wedlock at seventeen years of age, Augustine now settled into cohabitation with the mother of his son Adeodatus, a name which means “gift of God.” When Augustine was eighteen years of age, he read Hortensius by Cicero which he afterwards described as a book that “altered my outlook on life” (Confessions, 3,4,7). Near the end of his pursuit of philosophy and rhetoric at Carthage, Augustine joined an oriental religious sect called Manichaesim, to which he gave his allegiance for at least the next nine years of his young life.

When Augustine returned to his birthplace after the completion of advanced studies, his mother barred him from the house. Monica made more strenuous objection to her son’s adherence to Manichaeism than to his cohabitation with a woman. With his proselytizing temperament, Augustine had already made converts to the Manichaen religion and told even his staunchly Christian mother that some day she too would become a Manichee. After having opened a school, Augustine found the environs of his native Thagaste too confining for his present ambitions. Even more distressing to him was the unexpected death of an intimate young friend; Augustine was disconsolate. Both of these circumstances in his life prompted him to leave his hometown rather hurriedly.

Augustine returned to Carthage. There at little more than twenty years of age, he read The Categories of Aristotle, a book on logic which helped shape the orderliness of his mind. There followed a gradual disenchantment with the Manichaen religion, but its ardent devotees prevailed upon their co-religionist to persevere. Their most distinguished teacher, Faustus, they promised, would eventually come to Carthage and respond to Augustine’s many questions. Faustus finally came, but his torrent of words was all fantasy and fable. Augustine’s disillusionment increased. To make matters worse, the students at Carthage proved to be reckless and disorderly with the result that Augustine’s level of job satisfaction as a teacher was pitifully low. Putting all these considerations together, Augustine determined to seek new horizons. It was only the cruel trick of deliberately deceiving his mother and leaving her praying for him patiently in a local chapel that enabled Augustine to sail for Rome with his partner and their son. Monica went home alone. Augustine tells us: “I went to Rome.”

A Young Urban Professional

Dissatisfied with the failure of Faustus to make a strong case for Manichaeism, Augustine shortly thereafter despaired of finding the truth. He became a skeptic. Augustine started teaching again and soon discovered that Roman students refused to pay tuition and fees. Eventually, through the influence of Symmachus, the Prefect of Rome, his own merits as a teacher and the important fact that he was not a Catholic Christian, Augustine secured for himself the prestigious post of Public Orator at Milan. This ambitious young man from a middle-class provincial family in far-off Africa had now become an upper-class urban professional who would surely catch the eye of the Imperial Court.


383-384 A.D. 383-384 A.D. Augustine, with family and friends, sets sail to Rome where he will teach, knowingly leaving his mother behind praying in a chapel. Monica returns to Thagaste.

384-386 A.D. 384 A.D. (Fall) Augustine is appointed official orator in Milan. 385 A.D. Monica joins Augustine in Milan. Augustine visits the bishop of Milan, Ambrose, and attends Sunday worship to hear the famed preacher. 386 A.D. Monica arranges a legally and sociably suitable marriage for her son. Augustine's partner, the mother of Adeodatus, returns to North Africa alone. Adeodatus remains with his father.

386 A.D. 386 A.D. Augustine has a great moment of conversion to Christianity in the garden of his residence in Milan.


Milan was a highly cosmopolitan city. Its sophisticated residents made fun of Augustine with his rustic North African accent. Not long after his arrival, Augustine visited the urbane and learned bishop of Milan, Ambrose, but the encounter had the nature of a courtesy call. More importantly, the meeting prompted Augustine to attend Sunday worship for the sake of savoring the eloquence of the famous preacher. Although first attracted by Ambrose’s delivery of the Gospel, it was not long before Augustine showed interest in the gospel of delivery. He became less critical of the Bible with its confusing contents and its inelegant style. Gradually he became open to receive its message. At the same time, through his interest in philosophy, he attached himself to an established circle of people who were conversant with the Christian religion and Greek Philosophers, notably Plato, Plotinus and Porphyry.

The story of the conversion to Christianity of Marius Victorinus had a profound effect upon Augustine because he was, like himself, a noted and respected rhetorician. Indeed his first-hand account with many people of keen mind, for whom faith and reason were certainly compatible, slowly convinced Augustine that Catholic Christianity was, after all, intellectually respectable. In the meantime, some of the writings of the Platonists put him in touch with what was deepest in himself, his own ability to conceive of the “world within,” that crucial link with the interior realm of the spiritual and the immaterial.

Monica, meanwhile, had joined her son shortly after his arrival in Milan. With her intrusive manner she apparently wasted no time arranging a suitable marriage for her son. As a result, Augustine’s unnamed mother of Adeodatus was summarily dismissed and returned to North Africa. Augustine withheld her name from posterity, undoubtedly out of personal respect for her, but also for the obvious reason that his Confessions were widely circulated during his lifetime as Bishop of Hippo. From the beginning, both parties were aware that their liaison was destined to be ephemeral. This is why “mistress” is conceivably an ill-suited word for depicting Augustine’s lover, his companion for more than a decade, and the mother of their son. There is no doubt in my mind that, in the long run, many years of living with this woman gave rise to some of Augustine’s mature and enlightened reflections on love and friendship, trust, human affectivity and fidelity in marriage.

Augustine then became formally engaged to a young girl who was two years below the legal age for marriage. While he agreed to the terms of this legally and socially acceptable union, he took up with another woman to satisfy his sexual needs. In a senate culture which greatly resembled our own, Augustine described himself as a man who was “hot for honors, money and marriage” (Confessions, 6, 6. 9).

Be that as it may, we ought not to overstress or exaggerate the sinfulness of Augustine’s youth and middle years. Very likely the stable relationship which he cultivated with the unnamed woman whom he loved contrasted significantly with other liaisons with little or no permanence. By remaining faithful to this woman for upwards of thirteen years, Augustine’s behavior contrasted sharply with the marital infidelity of this father. Also, he deeply loved both the woman and the boy. Her callous dismissal can be explained partially by the fact that the late Roman caste system discouraged people of different social status from marrying. There is in fact evidence to indicate that the Catholic Church countenanced such an informal liaison. ([Council of Toledo (400 A.D.) Canon 17]; c.f. also Augustine, 5,5.) Neither Monica nor Augustine give a good account of themselves in the preemptory dismissal of Augustine’s partner.

It was a period of strain both financially and professionally. While Augustine had friends in high places and they were good to him, the hard fact remained: he needed money and he needed a wife who had some. What then did Augustine do next?

He did what could not be predicted and what could not be explained. He resigned his teaching position, and he did it as abruptly as Monica had dismissed the mother of Adeodatus and sent her packing to North Africa. Except for some private tutoring, Augustine was out of work, having resigned his teaching position near the end of the school term.

What can we say about this uncharacteristic behavior? Not much with certainty, except to remark that Augustine appeared to be on the verge of a total rearrangement of his life. Augustine also manifested the symptoms of what we would today describe as a “nervous breakdown.” The facts of his life make it clear that the allurement of wealth and power, the possible governorship of a Roman province and prestige had lost their luster. Sex was the last stronghold to imprison Augustine as his erotic needs held out until the final stage of his conversion. The raging desires inside him were surely reflected in his prayer: “Grant me chastity and self-control, but please not yet” (Confessions, 8, 7, 17).

Augustine was determined to marry. In this matter, Monica was even more determined than he. In her mind, marriage was the only possible way for her son to live the Christian ideal. Augustine remained unsettled about the question of marriage. Although marriage might lead to wealth and power, it did not promise to satisfy his desire for wisdom. Perhaps, instead, it might lead him astray.

On this very question, Augustine engaged in earnest discussion with Alypius, his life-long friend. For those serious in the pursuit of wisdom, Alypius argues clearly and definitively in favor of the need for celibacy. Augustine was not so sure. At any rate, Augustine’s journey toward wisdom, begun with the reading of Cicero, had met with disappointment in the Bible, had been sidetracked with the Manachees and seemed to be far from having reached its end in the dry abstractions of philosophy. This ever-burning desire for wisdom was not, apparently, sufficient explanation for the dramatic turn of events in his life.

Two Stories of Conversion

Two things happened that nudged Augustine closer to the moment of conversion. The first was a simple story that provoked his thoughts. The second was an experience so mysterious and so profound that Augustine himself found it difficult to describe in his Confessions some ten years later.


387 A.D. 387 A.D. Augustine, his son Aeodatus and his friend Alypius are baptized on April 24 on the Eve of Easter in Milan by Bishop Ambrose in the Catehdral of Milan.

387 A.D. 387 A.D. Augustine leaves Milan and goes to the port of Ostia to return to North Africa, but is delayed for almost two years while the port is closed by a blockade. During this time, Augustine and Monica experience a common mystical moment when they talk about divine wisdom, describing the moment Augustine said: "We did for one instant touch it..." (Confessions 9.10.23-25).

387 A.D. 387 A.D. Nine days later Monica dies and is buried in Ostia. In 1430, Monica's body is taken to the Basilica di Sant' Agostino in Rome.


The simple story of conversion came to Augustine’s attention during the visit of another North African named Pontician, who happened to notice that Augustine owned a copy of the epistles of St. Paul. This prompted Pontician to relate the story of two public officials who had found themselves in a dilemma much like that of Augustine. Young and ambitious and engaged to be married, they were in steady pursuit of those pleasures that the world offered to them. Yet these two government employees were so deeply affected by the invitation of Matthew’s gospel (19:21) to sell all and give to the poor that they abandoned their possessions, gave up their careers in the imperial service, and determined to follow Christ in a life of poverty. So enthusiastic was their conversion that they inspired their fiancées to follow their example and to enter a monastery for women.


388-391 A.D. 388 A.D. Augustine sails to North Africa and goes to Thagaste where he founds a lay community. 389 A.D. Adeodatus, son of Augustine, dies in Thagaste. 391 A.D. Augustine is ordained a priest in Hippo. This picture is of the excavations of the Basilica Pacis, in Hippo, where Augustine exercised his ministries.

395-397 A.D. 395-397 A.D. Augustine succeeds Valerius as bishop of Hippo and founds a monastery for clerics in Hippo. He begins writing The Confessions.

397 A.D. 397 A.D. Augustine writes the Rule at the request of monks in the Hippo monastery when he moves from there to the bishop's house. The Rule was also adapted for monasteries of women.


The impact of this story forced Augustine to reflect upon his own life, as he tells us in Confessions: “Pontician told us this story and as he spoke, you, O Lord, turned me back upon myself. You took me from behind my own back where I had placed myself because I did not wish to look upon myself ” (8,7,16).

The second episode is more difficult to grasp. Here readers of the Confessions may wish that its author had been less artistic in the telling. Some scholars actually dismiss the event as though it were a literary fiction. Augustine heard the voice, “as if ” he says, of a boy or girl chanting a repetitious refrain: “Pick it up and read, pick it up and read.” (Confessions 8,12,29). Obediently he hurries to the spot in the garden where Alypius was sitting. There he snatched the epistles of Saint Paul, opened the volume and read the first text that met his eyes. It was Romans 13: 13-14. “No reveling or drunkenness, no debauchery or vice, no quarrels or jealousies! Rather put on the Lord Jesus Christ and make no provision for the desires of the flesh.” This is a powerful message for any reader of the Bible. It gets right to the heart of Christian life.

Why did it come to Augustine at this time? How did it affect him? Augustine shares this great moment of conversion with us in his Confessions:

“I had no wish to read further, and no need. For in that instant with the very ending of the sentence, it was as though a light of utter confidence shone in all my heart and the darkness of uncertainty vanished. For you had converted me to yourself, so I would seek not ambition in this world — (8, 12, 29-30).(Translation John J. O’Meara).

By this time Neoplatonic philosophy had laid the axe forever to the roots of Augustine’s materialism by instructing him that God exists beyond matter and that God alone endows the human soul with some remarkable powers. He also came to realize that the Manichees made a mockery of human freedom by insisting that all human activity was the net result of mechanical forces warring against each other. His persistent fascination with astrology finally succumbed to the conviction that the fault lies not in our stars, but inside ourselves. His distaste for the Bible was diminishing, thanks to the preaching of Ambrose, which presented new and challenging insights into the meaning of God’s words. The conflicting genealogies of Jesus as they were recorded into the gospels and so often ridiculed by the Manichees no road of this restless journey to discover that materialism, skepticism, rationalism and a self-centered psychologism were indeed all the wrong tracks.

It had been no easy path for Augustine to travel from doubt to certitude, from ignorance about God to his burning desire to possess God. But all along the way he found that every doubt contains some certitude. The one who doubts is at least certain of being alive and doubting. Without mystery, reason and intelligence offer no exit. The mystery of faith in God and the actuality of human freedom offer exits everywhere. Psychology that bends us back solely upon ourselves soon becomes mired in the pool of Narcissus. Religious faith that turns us towards God gives us the freedom of full, human life. This is how Augustine grew in his understanding of God and the mystery of human iniquity.

“I created a human being, not avarice; I created a human being, not highway robbery; I created a human being, not marital infidelity. — (Homily 3,9 On the First Letter of John).

397-411 A.D. 397 A.D. Preaches at Carthage during the summer and participates in the councils of Carthage. 411 A.D. Participates in Collatio of 411, a conference set to resolve the intense conflicts between the Donatists and the Catholics. Augustine had long been against the Donatists, who considered sacraments performed by priests who betrayed the Church during the times of Roman persecution null or invalid. Augustine opposed the movement, believing sacraments were instituted by Christ, not man. This conference resolved in favor of the Catholics.

412-413 A.D. 412 A.D. Augustine begins writing City of God. 413 A.D. The first chapters of City of God are published.

426 A.D. 426 A.D. Augustine leaves Hippo in the winter for his health; begins Retractationes.


When he searched within himself to assess the condition of his own soul, Augustine exclaimed, “I have become an enigma to myself ” (Confessions, 10, 33, 50). Turning within himself and being intent solely upon himself, he had found nothing but doubt and confusion. This sense of emptiness inside led Augustine to cry out for God and for himself: “But where was I when I looked for you?...I could not find myself, much less you” (Confessions, 5,2,2). Acceptance of mystery in human existence gave Augustine his first solid step in this understanding of God. The more he examined the puzzle and the more he searched the riddle that was himself, the more he felt a presence of God who was within him—“Yet all the time you were more inward than my inmost self...” (Confessions, 3, 6, 11)—“All the while I was outside, you were inside” (Confessions, 10, 27, 38).

Augustine never thought of himself as a saint; that we should regard him as a saint would indeed surprise him. When surrendered to God, his love for eloquence loosened his tongue in praise of God. When surrendered to God, his intellectual sharpness earned him greater eloquence and the understanding of profundities. When surrendered to God, his unquiet and restless heart became quiet and found rest in the silent mysterious presence of God that was always deep inside him.


430 A.D. 430 A.D. Death and burial of Augustine.

720-1337 A.D. 720 A.D. The year thought to be when the remains of Augustine are placed in the crypt of the church of San Pietro in Ciel D'oro, (Saint Peter of the Golden Ceiling), in Pavia, Italy. 1337 A.D. On January 30, 1327, Pope John XXII, grants the Order of Saint Augustine a house alongside Augustine's tomb affirming the Order's special bond with its spiritual head.


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May God bless you on your continued spiritual journey!

The article above was first published in the Spring 2015 issue of Augustinian Magazine, a publication of the Augustinian Province of St. Thomas of Villanova.


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