At the age of 31, in the summer of 386, Augustine converted to Christianity. And then, at the start of the Vintage holidays (August 22-October 15), he quit his job.

Augustine tells us in Book 9 of the Confessions that he thought it would be “pleasing” to God that he “should withdraw the service of my tongue from the market of speechifying, so that young boys who were devoting their thoughts not to your law, not to your peace, but to lying follies and legal battles, should no longer buy from my mouth the weapons for their frenzy” (Conf. 9.2.2; tr. Boulding).

Augustine’s distaste for his former career as a professor of rhetoric is evident throughout the first nine books of the Confessions. He claims greed led him to sell his “talkative skills” to students who “loved worthless things and sought falsehood” (3.2.2). While he did “try to teach them honestly,” it is clear that he still feels chagrined that he was involved in passing along the “tricks of the trade” (3.2.2).

Augustine left his teaching post at Carthage for a new position in Rome. He explains that while the higher pay and greater prestige were factors in his decision, his main reason for moving to Rome was his hope that his students would be more disciplined and less disruptive than his students had been in Carthage (5.8.14). His Roman students were indeed less likely to act like violent hooligans, but they had a practice of leaving one teacher for another so that they could avoid paying their fees. Augustine tells us that this behavior caused his heart to be “filled with hatred for these youths” (5.12.22). Unhappy in Rome, Augustine was able to attract the notice of Symmachus, the Prefect of the city, and secure a new and better position in Milan as a professor of rhetoric.

Augustine does not tell us much about the students in Milan and how they may have differed from those whom he taught in Carthage and Rome. But I think that we can safely suppose that Augustine also found his Milanese students lacking.

In thinking it over, I can’t help but wonder whether any student would have been able to satisfy Augustine. Perhaps too smart for his own good, Augustine seems like he would have had little patience for students who were not naturally bright, extremely motivated, and interested in the same questions and concerns as he was. His worldly ambitious but lazy students who caused disruptions, engaged in violence, and stiffed him his pay were probably the bane of his existence. I have zero doubt that he could not have endured the amount of emails and grade-grubbing that contemporary university professors deal with on a daily basis.

But even if his students had been more ideal, would Augustine have been happy teaching rhetoric in any city? Rhetoric teaches one how to persuade and to move one’s audience but does not necessarily require one to speak truthfully. As Augustine becomes more and more drawn to the truth of Christianity, it makes sense that he becomes less and less interested in his chosen field.

Still, it is a bit wild to think about the fact that Augustine quit his job. He—a boy from Thagaste who needed to wait a year to be able to afford school—became a professor of rhetoric in Milan, a major city of the Roman Empire, in a decade and a half. He had made it! Can you imagine a scholarship student from Tennessee getting a tenure-track position at Harvard and then just deciding to leave it all behind?

I think the magnitude of Augustine’s decision here can sometimes be lost on undergraduate students. While they certainly understand the pressure to find a high-paying job and make something of themselves, they might not be able to comprehend how hard it would be to reject a way of life that every aspect of their culture endorses. Moreover, they don’t have enough life experience yet to understand what it means to study for so long, break into a field, climb the social and professional ladder, and then choose to let it all go.

But as a professor myself who has been through the rigamarole (the grants, the cover letters, the postdocs, and the campus visits), I find it astonishing that Augustine, whose life up until this point had been so defined by his ambition and his desire to make a name for himself, was able to turn away from his own success and pursue a different kind of life. I am fonder of my teaching position than Augustine was of his, but I often think about his courage and his strength of will to be able to recast his life in his thirties, leave behind all he had accomplished, and take on a new way of living.

I think his is an example for us all to contemplate what it means to live well and to remember that we are not stuck in our roles and routines, even if it sometimes feels that way. We have the ability, like Augustine, to change course at any time and steer ourselves toward a better path.