Greetings Portable Income Earner!

Next Tuesday we’re continuing our “Everyday AI Hacks” series — and this time the spotlight is on travel. 

If you’ve ever tried to book an international flight and wound up staring at twenty tabs, three conflicting fares, and a layover that makes no sense, you know how maddening it can be.

I’ll show you how to use AI to simplify the whole process: from finding the best routes and fares, to spotting hidden costs, to making sure you don’t fall into the classic “day-off-by-the-dateline” mistake that once cost me a hotel night in Tokyo. 

We’ll also look at ways AI can help you plan trips that fit your portable income lifestyle — faster, cheaper, and with less stress.

You’ll leave with at least one concrete way to use AI that saves time, money, and headaches on your very next trip .

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

🔍 Recap: Use AI to Restore Old Black & White Photographs

Billable skills you can acquire with AI

Last week, Heidi and I picked up where we left off after our little technical adventure the week before. This time the wires held — and we dove into how AI can make your everyday freelance tasks easier.

👉 Watch the Replay

We explored:

• Turning transcripts into insights. Instead of slogging through a 45-minute replay, you can drop a transcript into AI and ask for the 10 key takeaways. Better yet, have it build a self-quiz so you know what stuck — no sixth-grade “pop quiz panic” required.

• Proofreading with precision. Rae asked a great question: can AI just bold the changes instead of rewriting the whole thing? The answer is yes, if you’re specific. For fiction writers, that means you can keep your dialogue authentic while still cleaning up typos and grammar.

• Canceling subscriptions the easy way. I walked through how I used AI to untangle a stubborn Vimeo account — drafting a polite (but firm) email that got results. Instead of wasting hours on hold, you can let AI handle the heavy lifting.

• Photos restored and reimagined. I showed how AI can take a smudged old Polaroid and bring it back to life in color and detail. One of the most moving uses I’ve found yet.

And of course, we had laughs along the way — like when Heidi admitted she had to tell ChatGPT: “Remember, I’m the person who can’t stand the canvas, so please stop using it right now.” If you’ve ever fought with a tool, you know that feeling.

The bigger point? These aren’t futuristic tricks. They’re real, practical ways to reclaim hours in your day, sharpen your proposals, and even rescue old memories. AI isn’t here to replace your skills — it’s here to free them up.

Bring your questions — and your curiosity.

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

QUESTION OF THE WEEK

Last Tuesday, the Q&A box was on fire — so many great questions that we couldn’t possibly cover them all live. 

So instead of just one “question of the week,” we’re giving you a rapid-fire round of the best ones (and some quick answers you can put to work right away):

“Can I give ChatGPT a YouTube video and ask it for 10 bullet-point takeaways?”

Yes — but only through a paid tool. The free workaround: download the transcript (most videos have one) and paste that into ChatGPT. Boom — instant summary.

“Can ChatGPT proofread and bold the changes?”

It can, but you’ll get better results if you’re specific about what you want: grammar only, typos only, leave dialogue untouched, etc. The clearer your ask, the cleaner your output.

“What’s a UTM — and do I need to care?”

Think of a UTM as a little tracker on the end of a URL. It lets you see where your clicks are coming from (newsletter, blog, social post). If you’re writing online content, UTMs = better data. Pro tip: ask ChatGPT to “explain it like I’m 5” — you’ll get a crystal-clear explanation.

“If I feed ChatGPT bullet points for an article, can I publish what it gives me?”

Short answer: yes, but add your own voice. AI output alone can’t be copyrighted. When your ideas and edits shape the piece, that blend is what makes it yours.

“Can I make ChatGPT write in my style (or someone else’s)?”

Yes! Give it a handful of your past writing samples and tell it, “this is my style — let’s call it X.” Next time, just say: “Write this in X style.” (And yes, you can have it channel Groucho Marx if you’re feeling cheeky.)

👉 These are just a handful of the questions we loved. Keep them coming! Got a burning “how-do-I?” Send it to us at [email protected] — you might see it featured in next week’s spotlight.

🎉 It’s that time again — the last Tuesday of the month means After Party!

Right after our regular call, stick around for Round 9 of Freelance Feud — our laugh-out-loud, fast-paced game where your freelancing smarts (and sometimes wild guesses) win the day.

✨ Why you don’t want to miss it:

• Connect live with fellow Barefoot Consultants members in a fun, no-pressure way.

• Pick up clever tips and reminders hidden inside the game questions.

• Walk away smiling — it’s the perfect reset at the end of the month.

🗓️ Tuesday, September 30 | 8:00 PM Central (immediately after the call)

Bring your wit, your curiosity, and maybe even your favorite beverage — because this round is shaping up to be the most entertaining yet.

👉 Don’t just learn with us. Play with us.

IF THIS IS YOUR FIRST TIME, CLICK HERE TO REGISTER ✅

🌍 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.