The Paradox: When Wisdom Meets AI

Part 4 of The Intentional Visibility Project: An 8-Part Series on Strategic Visibility for Accomplished Women Over 50

Previously: In Part 3, we explored why you are NOT the hero—your audience is. You’re the guide who’s already been on the journey. Now let’s explore what happens when that earned wisdom meets artificial intelligence.

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Inspired by Christopher Penn’s Almost Timely News article: Cultivating an AI Mindset, Part 1. Christopher teaches us how the engine works. I’m interested in where we drive once we understand the engine. Below is the direction I found myself heading toward: what happens when decades of human wisdom collide with artificial intelligence.

What Exactly is a Paradox?

Let’s start with what a paradox is.

Merriam-Webster’s Dictionary explains it as “a seemingly absurd or self-contradictory statement or proposition that when investigated or explained may prove to be well-founded or true.”

The origin of the word… it was first used in 1533 | Latin paradoxum, from Greek paradoxon, from neuter of paradoxos contrary to expectation, from para- + dokein to think.

And in her book Atlas of the Heart, Brené Brown invited me to think about the word in relation to how I operate: “the opposing elements of a paradox are inextricably linked. Even though the elements seem contradictory, they actually compliment and inform each other in ways that allow us to discover underlying truths about ourselves and the world.”

How I Partner with AI

There’s a moment when you sit down with AI that most people miss. They see a chatbot. A tool. A shortcut.

I see the New York Public Library at 42nd and Fifth Avenue. That massive repository of human knowledge, with its polished reading rooms and endless stacks of history and knowledge. When I work with AI, I imagine that the entire building is a backpack. Not to carry its weight, but a toolbox to engage with as I dance with possibilities.

My earned wisdom + AI’s endless paths of information = something that didn’t exist five minutes ago.

But here’s what’s breaking my heart: Progress is moving faster than we expected. As micro and solo businesses, we have this narrow window, before the noise takes over, and I see too many people busy trying to save time. Yet they’re missing the opportunity to create something better. The time-saving organically happens when you’re busy creating things that matter. Are you open to rethinking it?

Do We Need Another Hack?

More than 10 years ago, I wrote about my frustration with the word ‘hack’—how we’d taken a word that meant ‘to cut with rough or heavy blows’ for centuries, or more recently, what we call a bad taxi driver, and somehow made it aspirational.

Now I watch the same pattern playing out with AI. Everyone wants the hack, the shortcut, the perfect prompt. They want to hack AI like they want to hack the algorithm, hack their morning routine, hack their entire life.

But wisdom doesn’t hack. Wisdom builds.

Intuition as Recognition

Back to Brené, I’ve been into her new book Strong Ground this weekend. One of the many things she nailed is that intuition is recognition. It’s your body remembering every pattern you’ve survived. Every decision that didn’t destroy you. Every risk that taught you something essential.

AI cannot build intuition. It has no body that remembers fear, no scars from failures, and doesn’t know what success feels like. But when your real-life intuition meets AI’s ability to find the next word, that’s when you’re suddenly shown how to articulate what you’ve known in your bones for decades but could never quite explain.

This has happened to me over the past few months. I’ve always had a hard time explaining my work because it’s deep, and I get stuck explaining the tools and tactics that no one really cares about until they see how it can work for them. But I know I’ve honed in on the transformative nature of my work by the responses I’ve been receiving from people I’ve known for years. AI gave the wisdom of my work a vocabulary.

Throw Away the Instructions

Here’s the uncomfortable truth: Everyone wants to follow the instruction manual. Whether it’s beating the algorithm or prompting AI, they want the formula and the guaranteed result.

But you know what real wisdom does? It takes the carefully designed Lego fire station apart. Dismantles the ornate pirate ship. Then invites you to sit with the pieces and ask: “What else could this become?”

Most people over 50 have been rewarded in school and throughout their careers for building to spec. For following best practices. We’re the ‘you break it, you buy it generation.’ Now AI comes along, and inquires… why are we still seeking the instruction manual?

Meanwhile, the real opportunity is staring us in the face: You finally have a partner who doesn’t judge you for taking things apart.

The Algorithm Paradox Redux

What if we stopped looking for the “perfect prompt” and instead, we flipped it? What if, instead of saving time being the holy grail, we used AI to spend time differently? To go deeper instead of faster?

This is what Claude (my favorite AI tool of the moment) said to me:

“You said something that stopped me cold: People spend more energy trying to beat the algorithm than building relationships. They’ll do everything except the obvious—actually connect with humans.”

This spun us in a new direction. Someplace I did not expect to go. The next words Claude found became the basis for this article, which anchors so many of the topics I talk about, references to people I admire and learn from, and a blog post I wrote 10+ years ago. It is my content repurposing/upcycling Tried & New process in action.

Notice the Pattern?

By now, you might be seeing how the pieces we’ve explored so far connect. Your intentionality (Part 1) guides how you use AI. Your architecture (Part 2) determines what you build with it. Your audience understanding (Part 3) directs where you apply it.

AI doesn’t replace any of this foundational work. It amplifies it. But only when wisdom leads.

Evidence You Survived

Human wisdom is earned through experiences; it’s evidence that you made it through something harder—you can do this too.

This is it. This is what AI will never have. Not because it lacks data, but because it’s never had to choose between two impossible options at 2 AM.

Your wisdom isn’t just knowledge. It’s proof of survival.

When that evidence meets AI’s processing power, you don’t get artificial wisdom. You get articulated wisdom. Wisdom that finally has words, frameworks, evidence for what you’ve always known but couldn’t prove. Then you can create systems for upcycling what you’ve already created. The work that tells the beautifully intricate and messy story of your growth and trajectory.

The Choice

Christopher Penn’s article brilliantly explains how AI works—the technical architecture, the patterns, the probabilities. That’s essential knowledge; everyone needs to read, listen, or watch to understand how it works.

But there’s another conversation we need to have: after we understand how AI works, what happens when it paradoxically meets humanity? Something that doesn’t operate on probability? Human wisdom that knows when the probable answer is exactly wrong.

Stop trying to save time. Start trying to create what doesn’t exist yet.

The fire station instructions will wait. So will the pirate ship blueprint.

Why not have some fun… dump all the pieces on the floor and build something nobody’s seen before.

That’s where wisdom meets AI. Not in the instruction manual, but in the mess on the floor, where experience knows which pieces don’t belong together—and puts them together anyway.

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This is Part 4 of The Intentional Visibility Project, an 8-part series exploring the strategic architecture of lasting visibility for accomplished women over 50.

Previously: You are NOT the Hero. It is NOT Your Journey… It’s All About Your Audience — Part 3

Next in the series: Your Content is the Mixtape of Your Wisdom — Part 5, where we explore how to curate your earned wisdom into something that resonates.

Donna Cravotta is founder of Cravotta Media Group, host of The Real 50 Over 50 livestream, and creator of BeVisible.club. She guides accomplished entrepreneurial women 50+ as they architect strategic visibility that matches the significance of their work.

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