Happy birthday Augustine (354-430 CE)—the famous procrastinator and overthinker who stole pears, failed spectacularly (at least in his desire to be good all the time), and finally decided to become a saint—then wrote a million words confessing it, all while trying to figure out how to be good. I actually read about him and very well resonated with him. I think a lot of overthinking, introspective people would too.
(Making him human, despite his philosophical genius)
So, imagine: You’re a smart, ambitious, and well-educated young person in the Roman Empire. You’re:
You’re skeptical and wish to explore—saying something like “Mom, it’s not a big deal. I’m into philosophy and exploration. I will get this sorted, just not now…”
You are feeling… literally empty. Something’s missing—even when you think you have everything that the world considers constitutes a good, successful life. You know what you want to do or should do to be a good person, but you keep messing up—you can’t stop doing things you later regret.
The comedic tension in his life was that he was too self-aware, but does regretful stuff.
(The main inciting incident was rather a very minor, relatable incident—but not to Augustine)
When he was a teenager, he and his friends stole some pears from a neighbor’s tree. They didn’t even EAT the pears. They just… threw them at pigs—as it wasn’t good.
Normal person: “Ah… I was a stupid kid, but it was fun.”
Meanwhile, Augustine: writes entire chapters… “Holy christ! WHY did I do this? I wasn’t hungry! I knew stealing was wrong, even the fruit wasn’t good…”
Thirty years later, he’s a bishop. A leader in the church. Respected and holy.
And he STILL can’t stop thinking about those pears.
Augustine wasn’t stupid. He knew about Natural Law—this philosophical idea that basic right and wrong are obvious to anyone with a brain.
But he did it anyway. And that’s what haunted him: “If right and wrong are so obvious, why can’t I stop doing wrong?”
Straight-faced or Feynman translation:
Augustine stole some pear fruits as a teen but couldn’t forgive himself. This tells about his mind—he couldn’t easily let go of past or anything.
Therapist: “Gentleman, what brings you here?”
Augustine: “I stole pears when I was 16.”
Therapist: “Okay, you clearly don’t steal pears now. Have you done anything regretful recently?”
Augustine: “I have a lot of things. I literally am writing all of it. I guess this all started when the beginners of life (Adam, Eve) ate apple from that tree.”
Therapist: notes down “There is a pattern of some issue with fruits.”
He is sitting in a garden, feeling completely broken inside. He hears a child’s voice saying “tolle lege”—which meant “Take up and read.” Randomly, opens a page and reads a passage about giving up worldly pleasures.
DRAMATIC CONVERSION: Had a psychological breakdown of the structure in his mind and then got into Christianity.
He was a very normal person. What made him a genius was the same thing which made him worried about everything—he pondered on vague WHY-type questions, and even came up with good answers which were later agreed upon. And honestly, who knows who would be considered a genius in the future? There’s a good chance that’s any of us. But we would only know if we write our thoughts and reasonings down. This idea inspired me into writing. Now, coming to his ideas.
The Problem: “WHY do I keep doing bad stuff even when I know that it’s bad?”
The Augustine Attempt (not literally—but same content):
We are all born with some bugs in our operating system (mind)—and blamed them upon Adam and Eve. Typical overthinker move after whole night thinking on life choices.
The Feynman or Straight-Faced Translation:
He noted that we are all capable of doing mistakes on purpose—just for the sake of fitting in and appearing cool, or to feel accepted.
The Modern/Real Life Example:
All of us have probably done something we knew was wrong just for the thrill or social cool. Maybe we cheated on tests. Maybe we went along with imaginary lies and something wrong which may seem foolish now. We would surely have exaggerated or made up things to seem cool, or at least I did.
Is this the ANSWER to why we do these things? I’m not sure. But Augustine was one of the earliest people to obsess over this question—which is relevant even now. But Augustine was seeing something real—the gap between knowing what’s right and actually doing it.
The Problem:
The Augustine Attempt:
“Um… Maybe we have free will, which is why we can do mistakes or sin—that’s a major reason why evil exists. But we need God’s grace to actually choose good, which we can’t plan or earn. God just gives it to whoever He chooses, which… um… makes God unconditional.”
The Straight-Faced/Feynman Translation:
Augustine was so smart that he could spot every contradiction in his own arguments. Emotionally, though, he was committed to certain beliefs, so he just kept writing, hoping he’d solve it. Spoiler: he never does. But my god, the effort! It almost seemed as if he invented introspection. Writing was his therapy, and Confessions, his autobiography, became one of his most notable works.
(This was one of his brilliant answers)
The Problem: “What is time?”
Augustine’s insight:
“The past doesn’t exist anymore. The future doesn’t exist yet. The present is just an instant with no fixed measure. So… what IS time in the true sense?”
His Answer: Time exists in the MIND.
We just have:
Time is psychological, not just physical.
Feynman translation:
“Augustine noticed something weird: time is really hard to pin down. When you try to grab ‘the present,’ it’s already the past. He suggested time might be something our consciousness creates. Modern physics shows time is even more complicated, but as usual, he was attempting the right questions.”
This is actually advanced—he made overthinkers like us proud. Think for long and you might hit upon something: Philosophers and physicists still argue about whether time is objective or subjective. Augustine seemed like he was on the right reasoning.
Before conversion:
“I want to be good… but not YET. God, give me chastity and continence, but not yet!”
(This is a REAL quote. He really prayed “make me good, but not right now!”)
After conversion:
“Okay God, I’m ALL IN. Take my entire life, take everything. I will become a priest. I will write a few million words about you. I’ll never stop writing about sin.”
The comedy was: He went from “let me enjoy life a BIT longer” to “EVERYTHING IS SIN AND WE’RE ALL DOOMED WITHOUT GRACE.”
The internal conflict was and is REAL.
That thing where we KNOW what we should do but can’t make ourselves do it? Augustine described it perfectly. He seemed to understand the psychology of temptation and weakness.
Everything is about sin:
Feynman insight:
“Augustine had one insight—humans have an internal conflict between desires and ideals—and turned his mind into an entire narrative exploration of this idea.”
While reading this, I can’t help but laugh at how he took guilt to a totally pro level. But it also made me realize that he was trying to understand why humans struggle so much with desires versus ideals.
Even if I don’t agree with everything, Augustine was one of the first people to really explore the “why” behind human weakness. That tension between what we know we should do and what we actually do? That’s very real—we all experienced it. And he dived deep into it, so we could all relate to it.
I’m not concluding we need to stress about every thought or desire like he did. But noticing these conflicts in ourselves—and maybe writing about them—is actually kind of useful. Kind of like doing a mini-autobiography of your brain, a mini therapy.