Why Wisdom, A Sequel To My Own Thoughts
When I first wrote about wisdom, I thought I had something meaningful to offer. I believed I had something solid.
After all, that was part of the reason why I hit publish!
But looking back now, I see that what I had was mostly wishful thinking wrapped in a few intellectual insights that, frankly, don’t hold up anymore. I’d love to tell you that I’ve gained profound clarity since then, that my understanding has deepened, and that I’m closer to the truth.
But the truth is, I’m more confused than ever. And that, I think, is where the real work of wisdom begins.
And its kind of hard to accept that confusion.
Facing My Naïveté: A Hard Look Back
My initial thoughts on wisdom were simple: a mix of moral clarity, intellectual rigor, and the ability to navigate life with some level of grace. I wrote as if wisdom were a set of principles you could internalize and apply, as if there were some endpoint to all this searching. I even thought that wisdom could be honed like a skill.
Now there is some truth in that, but I lacked a lot of nuances when applying that skill. And I still do. But the more I think about it, the more I see how naïve that was. That earlier version of me was looking for something fixed, a final state of understanding. I wasn’t ready to admit how much ambiguity wisdom actually demands let alone how uncomfortable it is to live with that ambiguity.
Let's consider Socrates, whom many consider to be the embodiment of wisdom. By recognizing his own ignorance, Socrates rooted his wisdom, which was the exact opposite of what I thought I was doing when I tried to define wisdom with finality. Socrates never claimed to possess wisdom; rather, he spent his life questioning those who thought they did.
And therein lies the irony: the more I tried to define wisdom, the further I moved from it. I was searching for answers, but wisdom comes from understanding that you don’t have them.
It’s the same kind of thinking that plagued me in my earlier writing: the belief that clarity and conviction equaled wisdom. But clarity, I’ve come to learn, is often a false comfort. It lets us believe we’ve arrived at a destination, when really, we’ve just stopped asking questions.
The Realization: Wisdom Isn’t Certainty
If there’s one thing I’ve learned since, it’s this: wisdom has nothing to do with certainty. Nothing. Wisdom, as I now see it, is about coming to terms with not knowing, with the limits of my understanding. It’s accepting the fact that the answers I seek may never come. Or that when they do, they’ll bring more questions with them.
I used to believe that wisdom was about achieving clarity, but what if it’s actually about learning to live with doubt? The kind of doubt that doesn’t paralyze you, but pushes you to keep questioning, to keep seeking, even when the ground beneath you feels shaky. I see that wisdom might not be a set of truths, but a process. It is a continual, and often uncomfortable, engagement with the unknown.
If I was naïve before, I was even more so in believing that wisdom is synonymous with certainty. In my early attempts to grasp the concept, I thought that the clearer my answers, the closer I was to wisdom. The truth, though, is that certainty often disguises itself as wisdom.
It’s an enticing illusion. Being certain is a comfortable blanket that wraps around you when you think you’ve “figured it out.” But in reality, certainty can be dangerous, even foolish.
Take the 2008 financial crisis. The collapse of Lehman Brothers and the global economic meltdown was caused, in large part, by people who were absolutely certain about the markets. The financial elites had unshakeable faith in their mathematical models and the supposed infallibility of the free market. In his analysis of the crash, Nobel laureate Paul Krugman points out that these economic “wizards” placed their trust in complex algorithms, completely ignoring the warning signs of an impending disaster. Their arrogance, rooted in certainty, didn’t just cloud their judgment. It led to one of the most devastating financial events in modern history.
Was this wisdom? No, it was the direct consequence of mistaking confidence for understanding.
The complex truth is that wisdom thrives in ambiguity. It isn’t about having all the answers, as it’s about knowing when to question your own. And the more I reflect on my earlier thoughts, the more I realize that uncertainty isn’t something to be avoided, but embraced.
That’s the hard part: coming to terms with the fact that wisdom is less about answers and more about the willingness to live with questions.
Emotional Depth: Why Feelings Matter More Than I Thought
Our minds become paralyzed without emotions.In my original thinking, I didn’t give emotions much weight. I focused on the intellectual side of things. In my original thinking, I didn't give much weight to emotions because I was so focused on how wisdom was tied to reason, moral philosophy, and rationality. I didn’t want to admit that emotional intelligence might be just as crucial, if not more so.
I was wrong to overlook it.
It’s now clear to me that wisdom involves understanding and regulating emotions. It’s not the absence of emotion but the ability to sit with difficult feelings that define wisdom. The discomfort we feel in moments of failure, doubt, or uncertainty isn’t something to push away. It’s part of the process. Wisdom might not be found in avoiding pain or confusion, but in learning to stay with it.
I used to dismiss emotions when it came to wisdom, viewing them as distractions that clouded clear thinking. Feelings, in my mind, were obstacles that got in the way of reason and clarity. This was naïveté, plain and simple. I saw wisdom as the pinnacle of rational thought, like some perfect algorithm for human behavior. Emotions? They were too unpredictable, too irrational.
But I was wrong. Deeply wrong.
Let’s look at the failure of empathy in the COVID-19 pandemic. Despite the staggering global death toll and immense suffering, empathy became a political battleground rather than a common human response. The refusal to wear masks or get vaccinated in some communities wasn’t based on reason or evidence but on emotional defiance, which masqueraded as personal freedom. It turns out that emotions such as fear, frustration, anger, drove people’s decisions more than any rational discourse. In an interview, psychologist Paul Slovic points out that while statistics should motivate rational action, they often don’t; emotions do.
My mistake assumed emotions diminished rational thought. It’s quite the opposite. Neuroscientist Antonio Damasio has long argued that emotions are fundamental to decision-making. In fact, people with brain damage affecting their ability to feel still struggle to make even the simplest decisions.
Without emotions, our minds are paralyzed. In my earlier attempts to understand wisdom, I ignored this reality, preferring to believe that wisdom could be purely intellectual. But that’s a half-truth at best.
Humility Is A Hard Lesson
Perhaps the hardest lesson I’ve learned is that wisdom requires a kind of humility I didn’t anticipate. I thought wisdom would make me feel more secure, more confident in my decisions and understanding. But in reality, it’s made me less certain about almost everything. I realize that the more I learn, the less I ought to cling to any one idea.
This isn’t a simple thing to accept. It’s frustrating, even painful at times. We’re wired to want closure, to seek certainty, to feel like we’ve “figured it out.”
But the uncomfortable truth is that wisdom often leads you in the opposite direction. It asks you to sit with ambiguity, to question your own assumptions, to remain open to the possibility that you’re wrong.
In this way, wisdom isn’t about being right. It’s about being willing to be wrong, again and again, and learning to keep going despite that.
Wisdom, as I see it now, is not a trophy you get to place on a shelf. It’s more like a shadow that changes shape depending on the light.
And maybe that’s the best I can hope for: to stay humble, stay questioning, and to keep learning from the shadows of what I don’t know.
Would you consider a follow?
https://asymmetriccreativity.medium.com/
Bibliography
Plato, Apology, in The Dialogues of Plato, trans. Benjamin Jowett (New York: Random House)
Paul Krugman, The Return of Depression Economics and the Crisis of 2008 (New York: W.W. Norton & Company, 2009)
Paul Slovic, “The More Who Die, the Less We Care: Confronting the Deadly Arithmetic of Compassion,” Foreign Policy, February 26, 2021
Antonio Damasio, Descartes’ Error: Emotion, Reason, and the Human Brain (New York: Harper Collins, 1994)
