The Newsletter That Almost Didn't Happen (Because I Was Eating Feta in Greece)
Where I've been for 2 weeks (and the AI lesson hidden in Greek islands)
Hi friends,
So... remember that reliable Wednesday newsletter you've come to expect? The one that shows up like clockwork with AI tips to save you time?
Yeah, about that.
[Checks calendar]
It's been two weeks of radio silence. Not a peep. Nada. Zilch.
And before you unsubscribe, thinking I've abandoned ship, let me explain with a story that perfectly captures why we're all here learning about AI in the first place.
The Honeymoon We Never Had (Until Now)
Picture this: It's 2020. My wife and I just got married. We had big honeymoon plans – Greek islands, sunset dinners, the whole nine yards.
Then Covid showed up, and came with PACKED BAGS, it was here to stay. And decided to lock all of us down…so no Greece honeymoon.
Fast forward five years. I told myself, “Self, if you are still here and married 5 years from now, you will make good on this Greece trip.” It was major bucket list material for my wife, and I knew I had to fulfill it.
And here's where it gets interesting...
I 100% did not bring my laptop. When I first told my wife this, she didn’t believe me. (I had reneeged on that promise in the past.)
But I was dedicated to making good on this promise.
What Happens When You Actually Step Away
On Day 5 in Santorini, after visiting Athens and Hydra and Paros and others, I'm sitting at this tiny taverna overlooking the caldera, watching the sunset paint everything in a golden blue hue. My phone buzzes.
It's a text from Richard, who runs a barbershop in the ATL: "Big Homie, that scheduling assistant you helped me set up? It handled 47 bookings last week. I didn't touch my phone once. This is amazing."
I smiled, took another bite of this legendary Gyro (Greece’s street food is undefeated), and realized something profound.
This. THIS is why we're doing all this AI stuff.
The Conversations That Mattered
Even on vacation, I couldn't help having conversations about AI. But not the nerdy, technical kind. The human kind.
In Athens: Met a restaurant owner struggling with social media. Showed him how Claude can write Instagram captions in Greek AND English in 30 seconds. He literally hugged me.
During our romantic boat cruise in Santorini: Met an American couple who worked in the pharmaceutical space. Show her the possibility of having an AI Research tool to cut her time having to research into companies coming their way. We are getting dinner with them in Chicago next time they are in town.
On the ferry to Hydra: Talked to a yoga instructor from Germany who was burning out managing her online booking system. Introduced her to N8N + AI. If we are ever in Germany, free sessions will be available to us!
At a famous lake bar cabanna situation in Vouliagmeni: A restaurant owner from LA, who told me to put him in my phone as ‘Angelo The Greek’, mentioned spending 4 + hours a day on repetitive tasks. Spent 20 minutes showing him how to create AI email templates, among other things. My wife and I can now eat for free anytime we are in LA at any of his establishments.
But here's what struck me most...
None of these people cared about the AI itself.
They cared about what it gave them back.
Time with family. Energy for creativity. Freedom to actually RUN their business instead of being run BY it.
Angelo is mostly retired, and his son runs most of the business now, but he still loves to find himself in the day-to-day.
The Work I Did (And Didn't Do) From Paradise
Let me be brutally honest about working from a Greek island:
What I thought I'd do: Wake up early, knock out 2-3 hours of deep work, then beach.
Then, when I decided not to take my laptop.
What actually happened: My wife is an adventurer, so we were up early every day, she was in her paradise and she was going to maximize that time she had lol. So we woke up, ate an incredible breakfast, drank too much freddo espresso (iced coffee that Greeks have PERFECTED), and feel zero guilt about it.
And you know what? My business didn't burn down.
Why?
Because I've spent the last year building AI systems that handle the repetitive stuff:
The ironic part? I built these systems, thinking they'd help me work more efficiently. Instead, they helped me work... less.
The Realization That Hit Me Like Greek Lightning
Sitting on a beach in Paros, watching my wife read a book while the Aegean Sea did its impossibly blue thing, it clicked.
We've been thinking about AI all wrong.
It's not about being more productive. It's not about crushing it 24/7. It's not about scale or optimization or any of that Silicon Valley nonsense.
It's about this: What if you could run your business AND have a life?
What if you could:
Take a real vacation without checking in every hour
Make it to your kid's recital without your phone blowing up
Have a date night without mentally drafting tomorrow's social posts
Sleep in on a Tuesday because you felt like it
This isn't fantasy. This is what AI makes possible RIGHT NOW.
Here's What I'm Building Next (Because of This Trip)
The Greece trip clarified something I've been wrestling with.
Most AI courses and tools are built for tech people. They assume you want to become an AI expert.
But you don't. You want to become an AI USER. Big difference.
So I'm creating something new:
The "Set It and Forget It" AI Playbook
Five AI systems that, once set up (I'll walk you through it like you're five), run your business basics on autopilot:
The Email Answerer - Handles 80% of customer emails in your voice
The Social Presence - Posts engaging content without you writing a word
The Appointment Assistant - Books, confirms, and reminds without you
The Content Machine - Blogs, newsletters, and updates that sound like you
The Money Tracker - Invoices, follows up, and celebrates when you get paid
Each system takes about an hour to set up. Then it just... works.
Your "Try This Today" Challenge
Since I left you hanging for two weeks, here's something you can implement in the next 10 minutes that'll save you hours this week:
The Vacation Responder That Actually Helps
Go to ChatGPT or Claude
Type: "Write 5 email templates for common customer questions in my [business type]. Make them helpful, friendly, and include a clear next step."
Save these in your email drafts
Next time someone emails with a common question, copy, paste, personalize one detail, send
Time saved: 5-10 minutes per email
Sarah from that massage studio I mentioned? She used this while in Cabo last month. Answered 17 client emails in under an hour from her beach chair. With a margarita in hand.
The Golden Nugget (Screenshot This)
"AI isn't about working smarter. It's about working so much less that you forget you have a business for a few hours each day."
That's not laziness. That's the entire point of being a business owner instead of an employee.
Coming Back to Reality (Sort Of)
I'm back at my desk now. Same computer. Same view. New Water Bottle (Shout out Epic Universe)
But something's different.
I've tasted what it's like to trust my systems completely. To know the business runs without me. To be present – actually present – with the people I love.
And I want that for you.
Not in some distant future when you've "made it." Not after you hit seven figures. Not when you finally have time.
Now. This month. This week.
Because here's what Greece taught me: The perfect time to step back never comes. You have to create it. And AI is the tool that makes it possible.
Your Thought-Provoking Question
What would you do with an extra 10 hours per week if AI handled your repetitive tasks?
No, really. Stop and think about it.
Would you:
Finally write that book?
Learn to make sourdough?
Coach your kid's team?
Take random adventures?
Actually use that gym membership?
Just... breathe?
Hit reply and tell me. I read every single email (yes, even the ones from Greece, apparently).
Next Week: The Specific AI Setup That Ran My Business While I Was Gone
I'll break down the exact 5-tool system that kept things humming while I was eating my body weight in Gyros. With screenshots, step-by-step instructions, and the actual prompts I use.
But for now, close your laptop. Take a walk. Call someone you love.
Because the whole point of this AI revolution isn't to work more.
It's to live more.
Yamas! 🇬🇷 (That's "cheers" in Greek – you're welcome)
-Dex The Chicago AI Guy ❤️
P.S. – My wife just read this over my shoulder and said, "Tell them about the foot sucking fish incident." Next week, friends. Next week.
P.P.S. – If you're thinking "must be nice to take two weeks off," you're right. It IS nice. And it's not because I'm special or rich or lucky. It's because I spent 6 months setting up AI systems that do the boring stuff for me. You can too. Start with that email template trick above. Seriously. Right now. Before you forget and go back to doing everything manually, like it's 1995.
Time saved writing this newsletter with AI assistance: 0 minutes. Some things are worth doing yourself. But those 47 booking confirmations Richard didn't have to send? That's where AI shines.