Seasoned for the Singularity
When a cashier can’t make change even with a calculator, what does that say about tomorrow’s ability to challenge an algorithm?
Last week a young cashier counted my change…twice…consulted her phone’s calculator…and still slid a dime too much across the counter.
I made one attempt to assist before deciding to move on.
Ten cents isn’t life-changing, but the moment stuck with me.
Without a reference point – no mental math, no cash-drawer instinct – she had no reason to question the screen in front of her.
That’s the hidden gift of having lived a few decades: context that understands how things work IRL – without tech.
If you are in your 40s, 50s, or 60s, every market swing you’ve survived, every tough hiring call, every product that flopped now forms a pattern-recognition engine no large language model can replicate.
In the AI era, the deepest competitive edge is the seasoned mind that knows which questions to ask.
You’ve seen elegant theories crash on real-world rocks. When an AI generates a polished answer that feels off, you spot the wobble before the spreadsheet does.
Your intuition can be translated into sharper prompts.
The machine multiplies ideas; your insight chooses the keeper.
History’s detours have taught you where shortcuts cost too much. AI can crunch options, but only a wise leader can weigh them against values that outlast quarterly targets.
Three questions to keep front and center:
Does this result ring true with what I’ve learned the hard way
Where might my experience bias me against a breakthrough insight?
Am I still the final decision-maker, or have I quietly outsourced judgment to code?
Imagine pairing a rising manager fluent in prompt engineering with a veteran leader fluent in discernment.
One supplies breadth, the other supplies depth. Together they form a wisdom-AI flywheel that spins faster – and safer – than either could alone.
Technology multiplies answers; wisdom decides what’s worth acting on.
If you are in the latter portion of your life as a leader, please don’t run or turn a blind eye to the AI revolution.
Your experience is desperately needed – now more than ever.
Blessings to you, my friends!
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This Week’s Resource Recommendation:
"The Infinite Game"
- Simon Sinek
From Amazon: How do we win a game that has no end? Finite games, like football or chess, have known players, fixed rules and a clear endpoint. The winners and losers are easily identified. Infinite games, games with no finish line, like business or politics, or life itself, have players who come and go. The rules of an infinite game are changeable while infinite games have no defined endpoint. There are no winners or losers—only ahead and behind.
The question is, how do we play to succeed in the game we’re in?
In this revelatory new book, Simon Sinek offers a framework for leading with an infinite mindset. On one hand, none of us can resist the fleeting thrills of a promotion earned or a tournament won, yet these rewards fade quickly. In pursuit of a Just Cause, we will commit to a vision of a future world so appealing that we will build it week after week, month after month, year after year. Although we do not know the exact form this world will take, working toward it gives our work and our life meaning.
Leaders who embrace an infinite mindset build stronger, more innovative, more inspiring organizations. Ultimately, they are the ones who lead us into the future.
MMS 25-27
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