I Took Some Time for Myself!
But the Fridge Was Always Open... and So Was My Digital Mind!
Hey digital adventurers! Well, well, well... look who's back after disappearing for a whole month! I bet you thought I'd fallen into one of those productivity rabbit holes I'm always talking about and never made it back out.
It's been quite a year since I got back to writing about all this digital stuff we're passionate about. Over these twelve months, I've managed to build this incredible little community of nearly 400 subscribers (we're SO close to that milestone!) - and honestly, thank you SO much for sticking around, reading my late-night coding rants, and engaging with my experiments. You make this whole journey worthwhile!
As you've probably noticed... okay, you've DEFINITELY noticed... I went completely radio silent for the past few weeks. And I owe you an explanation because, let's be real, consistency is something I preach about when it comes to content creation and digital habits!
The Real Talk: Why I Disappeared
Two things happened that made me pump the brakes on everything:
First - The Writer's Block from Hell
You know that feeling when you have SO many projects running simultaneously that you can't decide which one is actually worth writing about? That's been my life lately! I'm literally doing like ten different experiments a day - testing new AI automations, building random apps at 2 AM, diving deep into knowledge management systems - but when it comes to sitting down and writing, I freeze up.
I keep thinking "Is this predictive calculation system I built for my self-learning to-do app interesting enough?" or "Should I write about this crazy MCP integration I discovered, or that automation that's saving me 3 hours a week?" It's like digital paralysis analysis!
My solution? I'm going to start sharing way more early-stage ideas with you. No more waiting until something is "perfect" or "complete." Sometimes the messy middle of an experiment is where the real insights live, right? And here's the thing - I'm planning to throw some polls your way from time to time. Let YOU tell me which direction sounds more interesting!
Second - Denmark, Campervan, and Digital Detox
I took the family on a proper campervan adventure through Denmark. We had Legoland and Legohouse booked (because when you're traveling with kids, some structure is non-negotiable), but everything else was beautifully flexible.
And you know what? I wanted to actually BE present. To look at Danish countryside without immediately thinking "how could I automate this experience?" Sometimes you need to step away from the digital optimization mindset and just... exist. Kind of like what I wrote about in my remote work reality check - sometimes the best productivity hack is just being human.
But here's the plot twist - even during my "digital detox," my brain couldn't completely shut off the innovation mode. Which leads me to today's experiment...
The Holiday AI Assistant Experiment
Okay, so I had this campervan trip with flexible plans, unknown territory, and that classic travel dilemma: "We want to see cool stuff, but we don't know what cool stuff exists around here!"
Instead of falling into the typical tourist trap of endless Google searches and review rabbit holes, I decided to build a proper AI travel companion. And honestly? It worked so well that I'm kicking myself for not sharing this approach sooner!
Here's exactly what I did, and trust me, you can replicate this for ANY trip:
Phase 1: The Route Intelligence
First, I fed our general route into Claude and asked it to analyze potential stops along the way. Not just the obvious tourist spots, but the weird, wonderful, and uniquely Danish experiences we might stumble across.
The prompt I used was something like:
"We're driving a campervan from [starting point] to [destination] through Denmark over 10 days. We have kids aged X and Y. Analyze this route and suggest interesting stops that aren't typical tourist traps - think local experiences, weird roadside attractions, beautiful nature spots, and places that would create memorable moments rather than just photo opportunities."
The AI didn't just give me a list - it created a geographic strategy. It identified clusters of interesting things so we could explore areas deeply rather than just driving past everything. This is exactly the kind of strategic AI usage I've been advocating for!
Phase 2: The Living Travel Brain
This is where it gets really clever, and it builds on that dynamic knowledge system I wrote about earlier this year. Remember my Dynamic Claude Chat guide? Same principle, but for travel!
I created a dedicated Claude Project and uploaded everything relevant:
Our accommodation confirmations
Initial rough plans and wish lists
The route we'd mapped out
Kids' interests and energy levels
Weather considerations
But here's the genius part - I connected it to a live Google Doc that I could update from my phone throughout the trip. Every time we visited somewhere, every spontaneous discovery, every "actually the kids are tired so we're changing plans" moment got logged.
This meant that every time I asked the AI "what should we do tomorrow?" it had perfect context of:
What we'd already experienced
How the kids had reacted to different activities
Our current location and energy levels
What we'd loved versus what felt like misses
The Magic Moments This Created
Instead of frantically Googling "things to do near [current location]" every morning, I could just ask natural questions like:
"We're near Aalborg and the kids are bouncing off the walls after two museum days. What's something active and outdoorsy within 30 minutes that won't require advance booking?"
The AI would remember that we'd already done three museum-style activities, that my youngest gets overwhelmed in crowds, and that we prefer experiences where we can park the campervan easily.
Or when we stumbled across an amazing local bakery, I'd update the Google Doc, and later the AI could suggest similar hidden gems in other towns based on what had made that experience special.
This is the kind of AI knowledge empire building I've been experimenting with - but applied to travel instead of work!
The Prompts That Actually Work
Since you're probably thinking "okay, this sounds cool but what do I actually SAY to the AI," here are the exact frameworks I used:
For Initial Planning: "Analyze our travel route and create a flexible framework of experiences rather than a rigid itinerary. Consider [specific interests/constraints] and prioritize discoveries that we couldn't easily find through standard tourism channels."
For Daily Decisions:
"Based on our journey so far [check the live doc], what experiences would complement what we've already done while matching our current mood and energy levels?"
For Problem-Solving: "We're dealing with [specific situation - weather, tired kids, mechanical issue]. What are our best options that turn this challenge into a positive part of the adventure?"
Why This Beats Traditional Travel Planning
Traditional travel planning is binary - you either over-plan everything and lose spontaneity, or you wing it completely and miss amazing opportunities.
This AI approach creates what I call "structured serendipity." You have an intelligent system that knows your preferences and context, but you're still free to be spontaneous. When inspiration strikes or plans change, your AI advisor adapts instantly rather than leaving you scrambling.
Plus, and this is crucial - it learns YOUR specific travel style. By the end of the trip, it understood that we prefer smaller crowds, that my family gets hangry around 11 AM, and that the kids are more adventurous with food when they're relaxed rather than rushed.
It's like having one of those digital tools that actually enhances your workflow instead of just adding complexity!
The Setup You Can Copy Today
Whether you're planning a weekend getaway or a month-long adventure, here's your action plan:
Choose Your AI Platform - Claude Projects work brilliantly for this, but you could also use a Custom GPT if you're in the ChatGPT ecosystem
Create Your Knowledge Base - Upload everything relevant: bookings, rough plans, travel constraints, group preferences
Set Up Your Live Update System - A simple Google Doc connected to your AI project works perfectly (just like in my automation framework)
Define Your Travel Philosophy - Tell the AI what kind of experiences you value versus what you want to avoid
Start with Route Analysis - Get that geographic intelligence working for you before you even leave
The beautiful thing? This scales perfectly from a simple weekend trip to complex multi-country adventures. And once you've used it once, you'll wonder how you ever traveled without an AI companion who actually understands your style.
What's Next for This Digital Traveler?
I'm already planning to expand this approach for business travel - imagine an AI that knows your work schedule, preferred meeting locations, and can optimize both productivity and local experiences during work trips! It's the next evolution of what I've been calling building internal digital solutions fast.
But for now, I'm just excited to be back and sharing these experiments with you. The creative energy that comes from stepping away and then returning with fresh perspectives... it's exactly what I needed.
And speaking of experiments - I meant what I said about sharing more early-stage ideas! Expect shorter posts about half-baked concepts, failed attempts that taught me something valuable, and those weird 2 AM coding sessions that sometimes lead to breakthrough moments. Remember my QR code generator built for just $4.25? More of that energy coming your way!
The goal isn't perfection. It's exploration, learning, and building cool stuff together. Just like when I wrote about finding the AI sweet spot - it's about knowing when to use these tools and when to just be present.
What do you think about the AI travel assistant approach? Have you experimented with AI for trip planning? Or maybe you've got completely different travel hacks that have transformed your adventures? Drop a comment below - I'm genuinely curious about how you approach the balance between planning and spontaneity!
PS. How do you rate today's email? Leave a comment or "❤️" if you liked the article - I always value your comments and insights, and it also gives me a better position in the Substack network.