What 800 Mayors Taught Me About Staying Human in the Age of AI
A 🧠 Head Check on how we adapt to change without losing ourselves
Last year I gave a keynote called “The Best of Both Worlds: How to Benefit From AI Now” to 800 mayors, council members, and city officials in South Carolina. Walking off that stage, I realized something: the real story wasn’t about AI at all.
It was about how we stay human while everything around us changes.
The Preparation Behind the Performance
When the Municipal Association of South Carolina first reached out, they had one request that made me laugh: “Make it fun. We’ve seen five AI presentations in the past six months, and they were all dry and technical.”
So we did something different. Instead of starting with algorithms and automation, we started with people. My team and I spent weeks crafting examples specific to city governance — how AI could help with grant writing, citizen feedback analysis, and meeting planning. But more importantly, we wove in stories about adaptation, trust, and the messy reality of being human leaders in a digital world.
The prep work revealed something crucial: most people aren’t afraid of AI because it’s complex. They’re afraid because change feels like loss of control.
I write about what happens when curiosity meets clarity — in investing, leadership, growth, and staying sane while building stuff. If you like this kind of thinking, you’ll find more over at Crazy Good on Substack.
What I Learned from 800 Nodding Heads
Standing in front of that ballroom in Greenville, watching city leaders react to my stories about my grandmother’s wisdom and my wife’s medical emergency, I saw something beautiful happen. The moment I stopped talking about AI and started talking about how we navigate uncertainty together, the energy shifted.
These weren’t just government officials anymore. They were humans dealing with housing crises, funding challenges, and public safety concerns — trying to serve their communities while figuring out if this new technology would help or hurt.
💓 Heart Check moment: The biggest applause didn’t come when I explained how AI works. It came when I said:
“Sometimes your goals require weird ideas. It might sound strange at first, but it could be the biggest thing you need right now.”
The Emotional Truth About Innovation
Here’s what I didn’t expect to learn: innovation isn’t really about technology. It’s about emotional resilience.
When I told the story of my wife’s bowel perforation (yes, I went there in front of 800 people), and how a simple cup of coffee solved what eight days of medical protocol couldn’t, something clicked. Sometimes the solution isn’t more complex thinking — it’s more human thinking.
The doctors said no coffee. Logic said follow the experts. But intuition said, “You know what coffee does.”
🧭 Gut Check: How often do we overcomplicate solutions because we’re afraid to trust what feels right?
Why “Best of Both Worlds” Matters Now
The phrase “best of both worlds” usually means having everything. But that’s not what I mean.
I mean integration. The ability to use AI’s computational power while trusting human wisdom. To embrace efficiency while preserving connection. To be logical and emotional, because as I told that audience: “You can’t outsmart emotion.”
This applies whether you’re implementing AI in city government or just trying to lead through any kind of change:
The Real Innovation Challenge
Walking through the hotel lobby after my talk, a mayor pulled me aside. “You know what struck me most?” she said. “When you talked about your dog Brad Pitt and how emotional connection outlasts everything else. That’s what we’re really trying to preserve in our communities.”
She got it. The challenge isn’t learning to use new tools. It’s maintaining human connection while we do.
🧠 Head Check: What if the goal isn’t to keep up with technology, but to keep up with our own humanity?
Your Turn
Whether you’re leading a city, a team, or just your own life through change, the question isn’t “How do I master AI?” or “How do I resist change?”
The question is: “How do I stay myself while becoming better?”
Because in the end, as I learned from 800 city leaders in South Carolina, the best of both worlds isn’t about having everything. It’s about being brave enough to integrate the new with what already works — your wisdom, your intuition, and your ability to connect with other humans.
Even when it feels weird at first.
Thanks for reading!
If you’re into ideas that mix insight, honesty, and a little irreverence, I’d love to have you on my Substack. Crazy Good is where I share the real-time ride — the wins, the pivots, and what I’m learning as I go.