After running around the streets of Thagaste as a kid, Augustine was sent off to school around 365. He was sent to Madaura, which was about fifteen miles away. It was what we would call a university town. It was famous for its school. Augustine would have studied the trivium: grammar, rhetoric, and logic. Cicero’s writing was a staple. Also on the reading list would have been Virgil, Ovid, and Seneca. Augustine wrote in his Confessions, “I loved it.”

He loved studying Latin and the great writers in Latin. And not only did he love it, but he was good at it. He was moved by the persuasive writing and the emotional expression, and this caused him to be, as we would say, all in. A medieval painting depicts Augustine with his nose in a book, while his classmates around him are being disciplined for getting into fights and being mischievous. As part of his studying and schooling, he offered a one-man reenactment of a scene from Virgil. It so took the audience, that he won the prize in the whole town for that year.

After four years in Madaura, he outgrew it. And while he excelled as a student, this is what he said, later in life, about his time there. He wrote in the Confessions after his conversion: “Let me tell you, my God, how I squandered the brains you gave me on foolish delusions.” He went back home, his head full of foolish delusions. He spent about a year at home while his parents raised money to send him to Carthage.

It was during this year as a sixteen-year-old that he committed his famous incident of stealing pears. In the Confessions, he said that he stole not because he needed the pears; in fact, he said he even had better pears back home. He stole simply for the sake of stealing, which is Augustine’s way of saying he was sinning merely for the enjoyment of sinning. He would say he was chasing after shadows.

When the time came, he was sent to Carthage. He was there for three years, and he completed his schooling. Again, as at Madaura, he excelled. But Carthage was not just a place of learning; it was also a cauldron of sin. The Latin word for Carthage is Cartago, and the Latin word sartago means frying pan, a cauldron. And that little word play, cartago sartago, was how Augustine saw Carthage. It was a cauldron of sin, and he felt as if he were in a whirlwind.

In 375 he went home for about a year to begin his career as a teacher in Thagaste. After that year, he went back to Carthage. As soon as he got there, he became quite famous. He had many students, but he didn’t quite enjoy them. In fact, at one point in the Confessions, he writes, “They come blustering into the lecture-rooms, like a troop of maniacs and upset the orderly arrangements which the master has made in the interest of his pupils.”

Not only did he teach, but he also began writing. In 380 he wrote his first book: On the Beautiful and the Fitting. It is lost to us in history, as are his other early books. All we can say is, Augustine’s star was rising. Fame was certainly coming his way. But in 383, he set sail for an even bigger stage: Rome. In the Confessions he writes that though he would get higher fees in Rome and have a greater platform there, he confesses those were merely the surface reasons.

He went to Rome to find happiness. So far, fame had not delivered the fulfillment that Augustine had been seeking. So he set his sights on true happiness, and he set his sights on Rome. What happens when he gets there?