Unsupervised Learning’s Daniel Miessler on Curiosity, Creativity, and the Power of Authenticity
Daniel Miessler has spent more than 25 years creating content at the intersection of technology, security, and human behavior. Today, his Unsupervised Learning newsletter and podcast reach over 700,000 followers, making him one of the most recognized independent voices in cybersecurity and AI.
Unlike many content creators chasing algorithms, Daniel isn’t focused on quick wins or viral moments. His work is rooted in curiosity, disciplined habits, and a belief that authenticity—not production polish—is what truly connects with audiences.
We caught up with Daniel to talk about his routines, his creative philosophy, and how AI is changing the way he works.
Here’s what he had to say.
How do you start your day?
A few years ago, I built a routine inspired by Andrew Huberman’s research. Sunlight, light weights, caffeine, deep focus work, reading, and daily walks—it’s a full set of practices I aim to follow.
Just as important is what I avoid: too much social media, mindless content, gaming, and negativity. When I do the good things, I feel good. When I slip into the bad ones, I don’t. I even wrote out two lists—what makes me feel better and what makes me feel worse. I have that list on my wall to remind me: don’t think, just do it.
What do people often get wrong about content creation?
Most people jump straight to thinking about content. But it really starts with you—what excites you, what sparks your curiosity. Einstein said it best: “I have no special talents, I am only passionately curious.”
The two biggest obstacles? First, losing touch with your childlike imagination. Second, only creating content you think the audience wants. The danger is that the second one kills the first. You end up speaking in someone else’s voice instead of your own.
You’ve been publishing since the late ’90s. How has your focus evolved?
Back in 1999, I was writing deeply technical content—networking tools like TCPDump and Nmap. Over time, my focus shifted to bigger questions: Where is AI headed? How will it reshape work? What skills will matter most in the next decade?
I’ve always wanted to understand how things work. And once I figure it out, I can’t help but share it. That cycle—learn something, write it down in my own words, then share it—has been my process for 25 years.
What’s the toughest part of building a community around deep ideas?
It’s a slow build. Flashy content wins quick attention. But if you’re focused on authenticity, you have to be okay with the long game.
Sometimes you’ll be overshadowed by creators with slick production. But people crave real voices. Some guy in Montana might sit in a chair and ramble for two hours and get 400,000 views—because he’s authentic. Meanwhile, someone with a $10,000 production rig gets a fraction of that.
Authenticity is the moat.
You’ve been vocal about AI. How has it reshaped your creative process?
For me, AI isn’t just a tool—it’s a partner. I built a personal AI assistant I call Kai. I’ll talk out an idea, and Kai will turn it into a structured blog post, even pulling in quotes and generating images. It’s the craziest output I’ve had in years.
But the real opportunity isn’t efficiency—it’s imagination. Stop asking what’s possible with AI. Start asking: What would you do with 10,000 employees? The only real limit is your curiosity.
Your work often touches on layoffs, skills, and the future of work. What perspective do you bring?
I think about who isn’t being laid off and why. It’s usually not a degree that saves someone—it’s mindset, adaptability, and the ability to shift quickly when things change.
We’re in a messy period, but I believe we’ll come out of it. The only way through is to talk about it in a positive way. If all we do is wallow in the negative, there’s no path forward.
What advice do you have for other creators—or anyone navigating big shifts in their career?
People have been trained to think their capabilities are whatever their job tells them they are. I want them to take the blinders off.
Forget the tools, forget the models. Just ask: What do you really want to do? Then go build it.
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