From Exploration to Integration
When the co-founder and “Senior Maverick” at Wired magazine, Kevin Kelly, speaks, you listen.
In our latest episode of What If? So What? Jim Hertzfeld sits down with Kevin Kelly, the Co-Founder of Wired magazine and one of the most respected observers of the digital age. Their conversation spans AI, organizational change, emotional technology, and the importance of staying endlessly curious.
It’s not about where the frontier is—it’s about how we navigate toward it.
“We discover things by using them.”
Kelly is quick to push back against the idea that insight can come from speculation alone.
“I think there’s a lot of Thinkism… the fallacy that you can figure things out by thinking about them,” he explains. “I think we discover things by using them.”
That simple shift—from theorizing to experimenting—is at the heart of innovation. He encourages direct interaction with new tools as the only real way to grasp their potential. “If I can’t use it, I want to talk to someone else who’s actually using them in some way. Because that’s where we’re going to learn.”
Innovation moves fast. Adoption moves differently.
While headlines often suggest exponential speed, Kelly brings the conversation back to reality.
“The frontier is moving very, very, very fast,” he says. “But the adoption is just going to take a long time… You can’t just introduce this technology nakedly. You have to adjust workflow, organizational shape… you have to adjust the infrastructure to maximize it.”
It’s not resistance. It’s pacing. And it’s a pattern we’ve seen before—he compares it to the slow but transformational adoption of electricity, which reshaped industries not just functionally but structurally. That same shift is playing out now with AI.
From digital to cloud to AI
Kelly observes that many companies aiming to embrace AI first seek to digitize, but that step alone may not be enough.
“There’s a step after digitization… which is they have to become a cloud company,” he says. “That’s really the only way that the AI is going to work at a large scale in a company like that.”
It’s not a warning. It’s a reflection—on what’s required to unlock the full potential of these tools.
When AI becomes emotional
There’s one dimension of AI that Kelly believes most people haven’t fully anticipated: the emotional bond.
“People will work with [AI] every day and become very close to them in an emotional way that we are not prepared for,” he explains. “It’s like… those who don’t have their glasses, and they need them to function. So, it’s not like falling in love with their glasses—it’s like, no, you are at your best with this thing.”
In that sense, AI won’t just reshape productivity. It may reshape the way we relate to technology altogether.
What does “digital” even mean anymore?
When asked to define “digital,” Kelly pauses. “At least in my circle, I don’t hear that term being used very much more,” he says.
But if pressed? He points to pace as the key distinction: not just whether something is digital or analog, but how fast it’s moving, how quickly it evolves.
That framing helps explain why some technologies feel modern and others feel legacy—it’s not just the format. It’s the momentum.
“You’re going to be a newbie for the rest of your life.”
Kelly closes the conversation with one piece of advice that applies to everyone, at every stage:
“No matter what age you are, you’re gonna spend the rest of your life learning new things,” he says. “So, what you want to do is get really good at learning… because you’re gonna be a newbie for the rest of your life.”
It reminds us that in a world of constant transformation, our greatest advantage isn’t what we know—it’s how we grow.
Listen to the full conversation
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Meet our Guest – Kevin Kelly
Kevin Kelly is Senior Maverick at Wired magazine. He co-founded Wired in 1993, and served as its Executive Editor for its first seven years. His newest book is Excellent Advice for Living, a book of 450 modern proverbs for good living. He is co-chair of The Long Now Foundation, a membership organization that champions long-term thinking and acting as a good ancestor to future generations. And he is founder of the popular Cool Tools website, which has been reviewing tools daily for 20 years. From 1984-1990 Kelly was publisher and editor of the Whole Earth Review, a subscriber-supported journal of unorthodox conceptual news. He co-founded the ongoing Hackers’ Conference, and was involved with the launch of the WELL, a pioneering online service started in 1985. Other books by Kelly include 1) The Inevitable, a New York Times and Wall Street Journal bestseller, 2) Out of Control, his 1994 classic book on decentralized emergent systems, 3) The Silver Cord, a graphic novel about robots and angels, 4) What Technology Wants, a robust theory of technology, and 5) Vanishing Asia, his 50-year project to photograph the disappearing cultures of Asia. He is best known for his radical optimism about the future.
Meet our Host
Jim Hertzfeld is Area Vice President, Strategy for Perficient.
For over two decades, he has worked with clients to convert market insights into real-world digital products and customer experiences that actually grow their business. More than just a strategist, Jim is a pragmatic rebel known for challenging the conventional and turning grand visions into actionable steps. His candid demeanor, sprinkled with a dose of cynical optimism, shapes a narrative that challenges and inspires listeners.
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