Quick note: I spent the weekend updating my archive and categorizing my posts since I now have over 100 published pieces! You can find the updated glossary of thoughts HERE. And you can always view all archived posts in chronological order HERE.
Last week, I wrote this piece on living a life you won’t regret, and it got me thinking more deeply about regret in general—and how arrogant some forms of regret can actually be. Last week’s post was about regretting the things we didn’t do. This post is a follow-up and is focused more on regret in regards to the things we did do, and the ways we look back thinking we “should have known better.”
I was about twenty-six when I first realized I might be addicted to my own mistakes. Not the making of them—God knows I'd have preferred to skip that part entirely—but the endless, meticulous cataloguing of them afterward. The way I'd replay conversations like a detective examining crime scene footage, zooming in on every micro-expression, every pause, every word that landed wrong. I thought this was consciousness… or growth. I thought this was what it meant to be a person who cared about myself. It took me years to recognize what was actually happening: I was drowning in my own pride.
To be stuck in regret is to think that you had full control over that past situation, instead of thinking maybe you were never as powerful or intelligent or wise as you believed.
This isn't the kind of pride we typically recognize—the chest-puffing, look-at-me variety. This is pride in disguise, pride that has learned to speak the language of humility while maintaining all the arrogance of its original form. It's the pride that says, “I should have known better” or “I should have seen this coming” or “I should have been wiser, kinder, more perceptive.” It's pride masquerading as self-awareness, when really it's just another way of insisting on our own omnipotence.
Literature is littered with characters who suffer from this particular affliction—the belief that their past selves should have possessed wisdom they simply didn't have access to yet. Take Jay Gatsby, whose entire existence becomes a monument to the arrogance of regret. His famous belief that you can "repeat the past" isn't just romantic optimism; it's a fundamental misunderstanding of how time and human consciousness work. Gatsby's regret over losing Daisy isn't really about Daisy at all—it's about his inability to accept that his younger self couldn't have known what he knows now, couldn't have acted on information he didn't yet possess.
Fitzgerald understood something profound about the nature of regret: it's often less about the thing we did or didn't do and more about our refusal to accept the limitations of our former selves. Gatsby's green light isn't just a symbol of longing; it's a symbol of the impossible demand we place on our past selves to have been as wise as our present selves pretend to be.
I think about this when I catch myself in those familiar spirals, when I'm thirty six analyzing the decisions of twenty-six-year-old me with all the wisdom that only came from making those exact mistakes. It's like expecting a child to have the emotional regulation of an adult, then being genuinely bewildered when they have a meltdown in the grocery store. The cruelty is stunning when you step back and look at it clearly.
Dostoevsky understood this dynamic better than almost anyone. His Underground Man, that masterpiece of neurotic self-awareness, spends the entire narrative trapped in exactly this kind of proud regret. He torments himself not just with what he's done, but with his inability to have been someone else entirely at the time he did it. "I am a sick man... I am a spiteful man," he begins, but what he's really saying is: I should have been a different person, and I'm furious with myself for having been exactly who I was.
The Underground Man's suffering isn't noble—it's narcissistic. His regret isn't evidence of growth or moral sensitivity; it's evidence of his fundamental inability to accept the basic human condition of learning through experience rather than omniscience. He wants to have been born knowing what he could only learn by living, and his regret is really rage at his own humanity.
Emma Bovary operates under a similar delusion, though hers manifests as romantic rather than intellectual pride. Her constant regret over her choices—her marriage, her affairs, her fantasies—stems from her inability to accept that she couldn’t have known as a teenager what would make her happy more than a decade later. She torments herself for not having been born with the wisdom to see through romantic fantasy, for not having intuited that real life would never match the novels she devoured as a girl. Her regret is really anger at her past self for having been naive enough to be young.
The Stoics saw this clearly. When Epictetus talks about focusing only on what's "up to us," he's not just offering a philosophical framework—he's providing an antidote to this particular form of spiritual poison. His famous distinction between what we can and cannot control isn't abstract philosophy; it's practical psychology for people trapped in the quicksand of their own regrets.
Marcus Aurelius, writing his Meditations to himself, repeatedly returns to this theme: the futility of raging against what has already happened, the impossibility of having been someone other than who we were. "Accept the things to which fate binds you, and love the people with whom fate associates you," he writes, and what he's really saying is: stop torturing yourself for having been human.
But there's something almost brutal about Stoic acceptance when you're deep in the throes of regret. It feels like giving up, like moral laziness. If I stop flagellating myself for my past mistakes, doesn't that mean I don't care? Doesn't that mean I'm not learning? This is where the pride reveals itself most clearly—in our attachment to our own suffering, our belief that our regrets are somehow more sophisticated or morally elevated than simple acceptance.
I've started to notice how some of us—and by some of us, I mean me, primarily—can become oddly attached to our regrets, the way people become attached to chronic pain. They become part of our identity, evidence of our depth, our sensitivity, our moral complexity. We curate them like art collections, polishing them until they gleam with significance.
There's something almost vampiric about it, the way we feed on our own past suffering. Lady Macbeth's sleepwalking scene isn't just about guilt—it's about someone who has become so identified with her crime that she can't imagine existing without it. "Out, damned spot!" she cries, but part of her doesn't want the spot to come out. Part of her has built her entire sense of self around that stain.
