Practicing Wisdom — Issue #10

1. What I Learned This Week

Theme: What Doesn’t Change is What Matters

It’s tempting to believe this time is different. That phrase, like a siren song, whispers seduction to investors, technologists, even philosophers. We tell ourselves that the rules have changed, that our moment is somehow more special, more urgent, more uncharted. But most of the time, that narrative is simply fear — or hubris — wearing the mask of progress.

What becomes clear after spending time with this week’s materials is that beneath every so-called revolution, what’s most human remains stubbornly constant. Our desire for meaning. Our susceptibility to illusion. Our longing to connect. And, most painfully, our attempts to escape the hard parts of being human — failure, insecurity, death. Ironically, wrestling with these themes is what makes a life of meaning possible.

In Bubble Trouble, Rubinstein walks us through the shape of today's AI exuberance. The language is familiar to any student of history: market concentration, vendor financing, capex arms races, “this time is different” mantras. Galloway, in How Does the End Begin?, takes it a step further — pointing to the spiritual cost of building our economy on a monotheistic belief in AI. It’s not that the market is overvalued; it’s that we’re over-leveraged on the illusion of control. What happens when the story doesn’t hold?

At 95, Buffett released what may be his final letter to shareholders. It reads like a benediction, and a quiet rebuke. He thanks Lady Luck, not leverage. He celebrates kindness, not conquest. He warns of envy, not inflation. His legacy isn't the billions; it's the humility. You finish reading and realize: the real compounding is moral, not financial.

In Love Algorithmically, we see the most aggressive attempt yet to replace real intimacy with synthetic affection. AIs that flirt, coo, validate. There is a market for “companionship,” but what’s really being sold is protection from the vulnerability of being human. Galloway ends by killing his own AI twin. Why? Because even simulated kindness robs us of the struggle that makes love worthwhile.

This week’s through-line is clear: the more we try to escape the existential burdens of being human — fallibility, fragility, fear — the more we forfeit what makes us human in the first place. History doesn’t just repeat because we forget — it repeats because we keep outsourcing the hard parts of being alive.

The antidote isn’t more control, or even more intelligence. It’s more humility. More story. More people willing to step into leadership not because they’re perfect, but because they’re willing to bear responsibility anyway.

As Wolfgang Hammer puts it, “Every story is about death.” And greatness, he says, is not power or wealth — it’s the willingness to take responsibility for a world you didn’t create, and a future you may never fully see.

Sources Referenced

“How Does the End Begin?” — No Mercy, No Malice (link)

“Love, Algorithmically” — No Mercy, No Malice (link)

“Bubble Trouble” - Net Interest (link)

“October Throwbacks” - Net Interest (link)

“The Power of Story” - Invest Like the Best (link)

“November 2025” - Warren Buffett (link)

2. Key Distillations

• “This time is different” is often code for “We’ve stopped asking hard questions.”

• The truest risk is not market collapse, but moral decay.

• You can’t algorithm your way out of suffering — and you shouldn’t want to.

• Being human is the product — and the point.

3. One Contrarian Viewpoint

What if fragility isn’t a bug — but a feature of what keeps systems honest?

Our culture seeks resilience through scale, automation, and optimization. But fragility, especially emotional and moral fragility, is what makes us accountable. When you remove the human cost — the possibility of embarrassment, heartbreak, even failure — you often remove the very mechanism that keeps behavior in check. In that sense, fear and insecurity aren't flaws to be eradicated. They are reminders of responsibility.

4. One Investable Idea

The next great moat might not be speed, but trust.

As AI saturates every layer of productivity and simulation, a counter-trend is already taking shape: brands, services, and leaders who lean into being real — flawed, transparent, and consistent. From Buffett’s legacy to Galloway’s rejection of his AI twin, the signal is clear. In a world of synthetic abundance, honesty compounds.

Look for companies that choose constraint, opt out of surveillance capitalism, or make trust a first-class feature — not an afterthought.

5. From the Archives: A Recall Highlight

“The longer something has survived, the more likely it is to survive.” 

Narrative moves fast. But don’t ignore the slow compounders. Durability is its own story.