The AI Aha Moment

When my daughter Rhiannon called me early one afternoon, she was buzzing. She and a friend were catching a train to New York for a concert at Forest Hills. The plan was classic Rhiannon: whirlwind trip, one night in the city, back to Virginia on Sunday morning. She was already stacking ideas for what to do with the precious few hours they had.

I suggested she let ChatGPT help her plan.

She laughed. "I don't use that."

Don't mistake her for a technophobe. Rhiannon has always been selective about her relationship with technology. She had one of the first Kindles as a kid and would dissect every iOS release with her sister like they were analyzing a Supreme Court decision. She's the one who showed me how to turn off those nagging voice directions on CarPlay.

But she's equally quick to abandon tools that feel like work. She has three different Facebook accounts floating around because she couldn't be bothered to remember a password. Her filter is simple: embrace the tech that extends your independence, ignore anything that feels like a chore.

So when it comes to ChatGPT, she sees it as the thing that got kids in trouble for cheating on essays. More fundamentally, she sees it as missing the point entirely. Why would she let a machine plan her perfect Manhattan day when discovering that day is the perfect Manhattan day?

For Rhiannon, wandering into the unknown bookstore is better than arriving at the optimal one. Finding the midnight slice joint through serendipity beats getting routed to the highest-rated pizza by algorithm. The inefficiency isn't a bug, it's the feature.

She's not anti-technology. She's pro-discovery. And she's suspicious of any tool that promises to optimize away the very experiences she values most.

By the time you read this, her trip will already be in the books. And I have no doubt she'll have wrung every ounce out of it her own way.

Here's the thing: I admire that about her.

But I also see how different her relationship with AI is from other people in my life — people who've gone from skeptic to believer in the space of a single moment.

The MRI Moment

A close friend of mine, who teaches elementary school, hurt her back recently and needed an MRI. When I suggested she try asking AI for help, she brushed me off. "I don't know anything about AI except bad things."

So I asked if she'd ever used ChatGPT.

"Oh, sure," she said. "That's where I research supplements."

There it was: the disconnect. "AI" sounded ominous. "ChatGPT" was already in her pocket.

While we were still on the phone, she uploaded her MRI results. Within minutes she sat stunned as ChatGPT handed back an interpretation that matched what her doctor had told her.

In that moment, the abstractions dissolved. "AI" wasn't a scary headline anymore. It was a tool she could trust because it confirmed something she already trusted — her doctor's voice.

That was her aha moment. The moment when a real problem got solved in a way that felt both surprising and trustworthy.

I've seen this shift from abstraction to experience before, in a completely different context. I grew up as one of the few Black families in Concord and later Lexington, Massachusetts, during the 1970s. My mom was the first coordinator for a program called METCO, where kids were bused out from Boston to suburban schools.

One time in high school, the METCO bus was boarded by several white kids who started a riot because they "didn't want those niggers being sent to our school." Later, I ended up in a prep school program with one of the instigators of that incident. We became friends. When I asked him what was different about me, he said I didn't "talk like I was Black" or "act like them."

The truth was simpler: I wasn't an abstraction anymore. I was the kid who'd been on his Little League team, who went to the same nursery school, who listened to the same music at friends' houses. The category dissolved into the reality of a specific person he actually knew.

That's exactly what happened with my teacher friend and ChatGPT. "AI" was a scary abstraction from headlines. "ChatGPT helping me understand my MRI" was concrete, personal, verifiable.

The Family Road Trip

Another longtime friend told me about a recent family adventure. She and her daughter flew to California for a conference. At the end, her son and her sister joined them, and they all drove back east together.

Her daughter planned the trip using ChatGPT. She gave it the parameters: where they were starting, where they were ending, how much time they had, and what the family liked. Out came a customized itinerary with meals, sights, and experiences they wouldn't have pieced together on their own.

The family didn't feel like the trip had been sterilized by technology. They felt like it had been enriched. They spent less time worrying about logistics and more time enjoying the trip.

Here's what struck me: the daughter didn't see this as cheating or cutting corners. She saw a problem — tight schedule, unfamiliar territory, need to balance everyone's interests — and reached for the tool that solved it best.

For her, ChatGPT wasn't controversial. It was just how you plan now.

Three Ways People Meet AI

I'm starting to see three distinct approaches:

The Skeptic has heard the horror stories and stays away. "I don't know anything about AI except bad things." They'll come around when they hit their MRI moment — when the tool solves a real problem they can verify.

The Bohemian guards the joy of discovery. They want to find that coffee shop, that bookstore, that perfect slice on their own. AI feels like cheating because the process matters as much as the outcome.

The Native doesn't overthink it. They have a problem, AI solves it, life gets easier. No philosophical wrestling required.

None of these approaches is wrong. But they reveal something important about how disruption actually works.

The Jetsons Problem

Neil deGrasse Tyson, the astrophysicist and host of StarTalk, said something recently about The Jetsons that hit me. The futurists behind the cartoon imagined flying cars — but they still had George Jetson piloting them.

That's absurd. If you've got the technology for mass flying cars, you've got the autonomy to fly them without human error. No society is turning millions of amateurs loose in three-dimensional traffic.

The problem is they focused on the shiny object and missed the systems shift.

That's what's happening with AI right now. People get stuck on the chatbot, the grading tool, the headline. They miss the bigger point: it's not about the tool itself. It's about how our roles and behaviors shift because the tool exists.

The MRI friend isn't just using AI to interpret medical results. She's learning to think differently about what counts as a second opinion.

The trip planner isn't just using AI for logistics. She's discovering that good planning multiplies rather than limits spontaneity.

The Real Pattern

Here's what I've noticed: widespread adoption happens when a tool solves a problem that isn't unique to one person.

Rhiannon doesn't feel she has a problem. For her, wandering around Manhattan is the solution. The journey is the destination.

But the teacher with the MRI? She had a problem millions of people share: medical anxiety in the gap between test and results.

The family driving cross-country? They faced the universal challenge of planning something complex with limited time and imperfect information.

The difference isn't generational. It's experiential. Some people encounter AI when they need something solved. Others encounter it as an abstraction or a threat.

What This Means

You don't change minds with jargon. You don't convert skeptics with acronyms like LLM or arguments about productivity gains.

You wait for their MRI moment. You help them find an experience that feels trustworthy and useful.

The teacher didn't become an AI advocate because I explained transformer architecture. She became one because ChatGPT helped her understand something she needed to understand, in a way she could verify.

The family didn't embrace AI because they read about its potential. They embraced it because it solved a real coordination problem they were facing.

Adoption isn't about age or tech-savviness. It's about encountering the tool when you need something solved, not when someone else thinks you should be excited about the possibilities.

The Question

The real question isn't whether you'll use AI. The real question is: when will you have your aha moment?

It might be an MRI that needs interpreting. It might be a family trip that needs planning. It might be a writing project that needs refining.

Or it might be that you're like Rhiannon — perfectly happy with the long way around because that's where the good stuff lives.

Both are fine. But here's what I've learned: the aha moment isn't really about the technology at all. It's about the systems shift that Neil deGrasse Tyson was talking about with The Jetsons.

We're not just getting flying cars. We're getting a world where humans don't have to pilot every decision alone. The question isn't whether AI will replace us — it's how we'll collaborate with intelligence that's very good at certain kinds of problems we actually have.

When that moment comes for you — when you stop dealing with the abstraction and start dealing with the specific — everything changes after that.