Greetings Portable Income Earner!

Ever tried reading a complicated contract or User Agreement without falling into a coma? 💤

We fed one to AI, and what came out was surprisingly useful (and way less boring).

Plus, we taught AI to fix grammar, spot contract traps, and make your writing sparkle—no law degree or grammar nerd badge required.

It was part legal clinic, part comedy show. Don’t miss this one.

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Don’t miss it —If this will be your first time attending, Register now

Proofread, Negotiate, Quiz, Repeat — we got a chance to see how AI can shave hours off your freelance work. 

We looked at:

• Contracts Made Simple: Upload a 29-page agreement and get a plain-English summary in seconds. Better yet, ask ChatGPT a real-world question like “What if my client wants to move off Upwork?” and get actionable, step-by-step answers.

• Proofreading with a Twist: Instead of clicking “accept” a hundred times, let AI reflow your whole article, highlight the changes, and even smooth it into travel-magazine polish.

• Comparison Power: Heidi shared how she used AI to compare old and new property management contracts — a lifesaver when hidden clauses can cost you.

Even when the tech glitched, the message was clear: AI isn’t about replacing your work — it’s about giving you sharper tools so you can deliver more in less time.

Next week, I’ll be back at full strength to cover the rest: photo tricks, quizzes, and AI-crafted email responses. 

Bring your curiosity and your questions.

Now here’s the news from the Barefoot Consultants’ world,

QUESTION OF THE WEEK

❓ Question from the Community:

What benefits might a writer gain from joining local writer groups, in addition to Barefoot Consultants?

Winton’s Take:
Even in our remote-work world, nothing replaces “flesh and blood” conversations.

Local writer groups give you a reason to step away from the computer, have a cup of coffee (and maybe a croissant), and talk shop with real people.

That grounding is critical — remote work can feel like a bubble if you let it.

What you don’t want to do is fall into the trap some writers push: insisting the “old-fashioned” way is better and ignoring platforms like Upwork. That won’t move your portable income forward. But engaging with peers about topics, tools, and trends? That’s invaluable.

Heidi added:
“It’s always a win to keep sharpening your skills. Whether it’s training, collaboration, or just talking it through with other writers, it helps you hone your edge as a freelancer. If you can do that in person — grab it!”

The takeaway:
Books and videos can teach you techniques, but human interaction gives you perspective, encouragement, and connections you won’t get otherwise. That’s why conferences like International Living’s are so powerful — you’re not just learning, you’re connecting.

🌍 Mark Your Calendars:
International Living 2026

If you’ve ever thought about combining travel with opportunity, this is your year. International Living is kicking off their first-ever Rome Conference on April 10th, 2026 — the perfect chance to explore one of the world’s most inspiring cities while gaining practical insights on living and working abroad.

Between events, Winton joked that maybe the smartest strategy is to “hang out somewhere in between” Rome and Mexico… but the truth is, each of these conferences offers something you can’t get anywhere else: face-to-face conversations, insider strategies, and the spark of community that makes this portable income journey feel real.

Winton knows from experience — one year, he stayed a full month in each conference city. It was exciting, but also a reminder that even digital nomads need a sense of home base and community. 

These gatherings give you both: fresh horizons to explore and real relationships to carry forward.

👉 Don’t miss it: Whether you’re looking at Rome in April, Mexico in late March, or one of the other destinations on the horizon, make space in your calendar. 

The ideas you’ll bring back — and the connections you’ll make — are worth every mile.

🎉 Don’t Miss the After Party: Freelance Feud, Round 9!

The month isn’t complete without our favorite community tradition — the Barefoot After Party. On September 30th at 8:00 PM (Central time, USA), immediately following our Tuesday Night Call, we’ll gather for Round 9 of Freelance Feud.

If you’ve never joined, imagine a mash-up of Family Feud, freelancer life, and plenty of laughs. 

It’s lighthearted, a little competitive, and the perfect way to cap off the month with your fellow Barefoot members. 

You’ll pick up insights without even realizing it — and walk away with a smile (and maybe bragging rights if your team wins).

👉 Get registered, bring your quick wit, and get ready for an evening of fun that keeps our community strong and connected.

  📅September 30th at 8:00 PM (Central time, USA)

CLICK HERE TO REGISTER ✅