Hard truth from my digital nomad days (plus the AI twist)

Author

Jeff Sauer
August 16, 2025

In partnership with

Why "lifestyle-first" entrepreneurs stay broke (and how AI might change that)

I've been thinking about a conversation I had years ago in Chiang Mai.

A friend pulled me aside at a coffee shop. Same question I heard constantly during my nomad days: "Jeff, what's the difference between us? We're both here, both entrepreneurs. Why are you successful and I'm struggling?"

I knew the answer immediately.

But it's not something you can say without sounding like a complete ass.

The difference wasn't talent. Wasn't luck. Wasn't even opportunity.

It was priorities.

He was lifestyle-first, business-second. I was business-first, lifestyle-second.

Same location. Completely different approaches.

The Rock and Pebbles Principle

You know that old demonstration where you fill a jar with rocks first, then pebbles, then sand?

For him, lifestyle was the rock. Yoga at 9am. Meditation sessions. Beach days. Work fit around everything else.

For me, business was the rock. Everything else was pebbles and sand.

This isn't about being a workaholic. It's about understanding what drives financial success.

Even people who make it look effortless - the "passive income" crowd - they all have their business rock in place first. Passive income is mostly myth anyway.

But Here's Where AI Changes Everything

For the first time ever, there might be an arbitrage opportunity.

I'm seeing it in my own work. Getting more done in less time. AI handling the heavy lifting on research, content creation, analysis.

Maybe - just maybe - you can be lifestyle-first and still build something substantial.

The efficiency gains are real. The time savings are real.

The Catch

This window won't stay open forever.

As AI becomes democratized, the advantage disappears. Everyone will have the same tools.

And here's the honest truth: even with AI making me more efficient, I'm not working less. I'm taking on bigger challenges. More R&D. Writing this newsletter on a Sunday night because that's when I have the headspace.

The fundamental principle still holds: business over lifestyle if you want financial success.

But AI is giving us the closest thing we've ever had to having both.

The Question You Need to Ask

Are you lifestyle-first or business-first?

Be honest. Your bank account already knows the answer.

If you're struggling financially but prioritizing everything except the work that drives revenue, that's your answer right there.

AI can help bridge the gap. But it can't change your fundamental priorities.

The rock still needs to go in first.

To Your AI-First Success,
Jeff Sauer

P.S. Speaking of putting business first - registration is open for our next AI-First Challenge. If you're ready to make AI your business rock instead of just another pebble, this is where it starts.

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