🪷 On Wisdom: Life's Compression Algorithm
I’ve long admired people who can effortlessly distill life's complexity into deceptively simple, deeply knowing insights. For years, I held certain assumptions about how they did this, but over time, I came to see that those assumptions were wrong.
Clarity and insight doesn't come from looming large, living fast, or knowing many. Nor does it come from success, wealth, or charismatic largesse. From what I can discern, the ability to see through complexity to an insightful end comes from slowing down, stepping back, observing carefully, and questioning persistently — all hallmarks of a deep, enduring, thirsty curiosity to really understand the world.
As children, we often see the adults around us as inherently wise, but as we grow, we begin to see through this illusion and come to realize that true wisdom is, indeed, rare. Despite this, our culture is saturated with wisdom — whole books devoted to it, countless movie and TV characters based on it, and, of course, social media feeds filled end-to-end with motivational quotes and catchy insights. What are we to make of this superficial abundance?
In a world exploding with chaos and overflowing with information and disinformation, how are we to distinguish genuine insight from well-packaged knowledge, opinion, or mere performance? More to the point: What is wisdom, and how do we define it? Why is it so rare, and what makes it so elusive? Where can true wisdom be found, and how can we best cultivate it?
One place to start is by recognizing what wisdom ISN'T.
What Wisdom is NOT?
I think we can all agree that wisdom is not mere opinion or sentiment. Nor is wisdom the shallow, performative, and ultimately hollow displays that overwhelm our social media feeds. True wisdom is far deeper and more enduring than the Mardi Gras-like masquerade on TikTok and Instagram.
Further, wisdom is not bound by personal experience or cultural norms; it can emerge from anyone, anywhere, at any time. Wisdom is also not limited to modern knowledge, and in fact, tends towards the domain of deeply resonant, timeless truths that have already endured for millennia. Finally and perhaps most insightfully, wisdom is not the exclusive domain of adults with their years of experience; how else could we explain the profound insights that often flow from the mouths of babes?
So what then is it — this wisdom?
What Wisdom IS?
A few months ago, I was talking with my mom about my young adult children who are both in their early 20s. After sharing the usual updates and running through their latest comings and goings, I opened up about something that had been on my mind for a while: While I take immense joy in watching my children build their own lives, I’ve started to feel that, as their lives grow and get bigger, my role in their lives is shrinking — becoming less central and less necessary. It’s a natural shift, but one that’s still hard to accept.
My mom, no stranger to offering insightful words yet never one to shy away from comforting me with easy reassurances, looked at me thoughtfully. Instead of offering a predictable response like, "You're not losing them; you're their father; you'll always be one of the most important people in their lives," she simply said, "Just keep being a father."
BAM! That folks, is wisdom. Pure and true.
Wisdom crystallizes experience. It compresses lifetimes, generations, even millennia of living and learning into deeply resonant insight, foresight, intuition, even common sense. It clarifies priorities and speaks truth. We recognize true wisdom the moment we hear it. We see it in the sudden reactions of others.
True wisdom resonates so deeply and uniformly that it stops us in our tracks — eyebrows raised, we knowingly nod or smile in quiet acknowledgment. True wisdom is perhaps the only thing we still collectively applaud, revere, and agree upon. This is the enduring power and important brilliance of wisdom.
Need vs. Want
My all-time favorite pearl of wisdom is the famous Dolly Parton quote: 'If you want the rainbow, sweetheart, you have to put up with the rain.' This is pure, consummate insight — simple, honest, true, deeply meaningful, and profound. Fourteen simple words, exquisitely strung together, precisely expressing the expectations and challenging hardships of growing up and dreaming big.
I believe we all have a responsibility to share the most important things we've learned with others. But too often, we don't. Despite our best intentions, we hold ourselves back from saying what sometimes needs to be said. We worry that we'll bother the other person (wisdom, a bother?), think they won't listen (they may not listen, but they will hear), or simply find it easier to tell those around us — especially those closest to us — what they want to hear as opposed to what they need to hear (not helpful). We think we're helping or being kind. We're not.
My mom could have said many things to me that day. She could have complimented my steadfast commitment as a father or talked about how much my children love me and will always need me. But she didn't. With those five simple words — 'Just keep being a father' — she resisted telling me what I may have wanted to hear and instead told me exactly what I needed to hear — precise and perfectly compressed wisdom. Personified.
The thing about true wisdom is that it's not just a teacher, but also a friend. My mom's words that day were like a heat-seeking missile, guiding me directly to an essential truth, one that instantly steered me away from conjecture and detours and completely reoriented my concerns and worries into priorities and responsibilities. They are my children; I am their father; they need a father — 'Just keep being a father.' Dam, that's good!
This experience reminded me of another encounter I'd had with wisdom years earlier. I had reached out to my mentor for guidance on a challenging business problem. The stakes were high, and time was of the essence — or so I thought. After explaining the situation to him, I expected a quick and easy response that I hoped to implement that afternoon.
Instead, he offered something far more valuable: he told me to do nothing and JUST WAIT. He warned me, "The right move will come, but this is a trap. Act now, and it will cost you dearly." What? This was the last thing I wanted to hear. I vehemently disagreed, but he pressed on: "...the difference between the right move and the wrong move here is significant. You’re being pressured for a quick decision for a reason. You can’t see it, but I can. Avoid the trap by doing nothing and just waiting. It’s your call, but if you act now, don’t call me when this bites you in the ass."
Tough words, right? True wisdom often is tough. And inconvenient.
Reluctantly, I relented. His advice to do nothing and just wait was exactly right. How did he know? Listening to my mentor's strong warning saved me from a storm of trouble that I had no idea was brewing, let alone one that might have caused my young company significant peril. This experience taught me the immense value of learned wisdom. It also taught me the value of asking for help, listening to people you trust, and the importance, sometimes, of doing nothing and just waiting.
Insight Through Expression
Above, I asked how my mentor knew something so central about my business that hadn't ever occurred to me? Recall his words, "You can't see it, but I can." Here we're introduced to a crucial feature of wisdom — it really does take a village. But, as I said at the outset, wisdom is not solely the province of older or more experienced people.
So what does it take to refine and sharpen life and living into wisdom, insight, and truth? The answer isn't easy or obvious, but at a minimum requires considerable time, extreme nuance, and tenacious habits of expression. Below are four of the most important:
Exquisitely careful observation — carefully attuning not only to what's said, but also to what remains hidden or unspoken.
Extreme curiosity — the kind that pushes you to ask questions others shy away from and seek answers beyond the obvious.
The courage to speak and hear the truth — the most challenging of all — even when that truth is inconvenient and uncomfortable.
Close, deep, empathic listening — not just to the words you hear, but to the expressions you see — the pauses, silences, and hesitations.
This is how we transform raw experience, over time, into wisdom that matters and resonates.
Wisdom Through Time
Ultimately, I came to understand two key truths about wisdom.
First, wisdom isn't easily grasped. While we can, and sometimes should, borrow wisdom from others, in order to truly understand and appreciate the depth of it, we need to experience life as broadly, boldly, and curiously as possible. We need to continuously process and reflect on our experiences. We need to ask questions over and over, and when we're done asking those questions, we need to formulate and ask more. And, we need to shape our own understanding of wisdom with courage, independence, and deeply critical thinking.
Secondly, our inability to immediately articulate and fully understand the true meaning of things is itself a form of wisdom. Finding true wisdom takes time. Also, though wisdom may be there for the taking, it is NOT FREE.
As for cultivating and developing my own understanding of wisdom, I decided to practice what I learned from my mentor all those years earlier — I waited.
Epilogue
Several years later, in a moment of either inspired madness or madness-inspired insight, I quite unexpectedly found myself spontaneously riffing on the question: What is wisdom and where can it be found? Part 2 of this essay is a series of statements — part declarative, part exploratory, part stream of consciousness — all in pursuit of capturing the essence of what wisdom has come to mean to me.
You can read it here.