Greetings Portable Income Earner!

If you’ve ever stared at Upwork and wondered where to begin, this session is for you. 

We’ll walk through small, “starter jobs” — the kind that are easy wins (beta reading, short content edits, simple transcription) but build the confidence you need to go bigger.

I’ll also show you why aiming too high right out of the gate can backfire, and how stacking early wins is the smarter path to momentum.

And for fun, we’ll pull up live job posts and brainstorm proposal openings together. 

Think of it as proposal practice — but with the whole community on your side.

👉 Don’t miss it — If you want an extra boost to get started, please join our upcoming 6 week workshop… details here.

Bring your curiosity — and your questions.

✈️ Recap: AI Trip Planning, Rome Edition

This past Tuesday, we tested AI with a high-stakes challenge: planning my trip to Rome. Instead of juggling 12 tabs, three airline sites, and a pile of notes, I gave AI the whole picture — dates, points balances, travel options — and let it run.

The result? Clear travel options, ways to stretch airline miles, and even a day-by-day Rome itinerary complete with “skip-the-line” tricks I never would have thought of. 

The big takeaway for you: don’t ask AI for one flight or one option — give it the whole picture. That context lets it return the kind of plans a human travel agent used to, saving you time, money, and a few headaches.

👉 Want to see exactly what I typed? Download the chat transcript below and use the prompts to plan your own next trip.

👉 Watch the Replay

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

QUESTION OF THE WEEK

Diane asked:
"I am working on creating a project on Upwork for myself. Any thoughts on where I might find training about it on the Barefoot platform?"

This is such a useful question, because the Project Catalog is one of the fastest ways to get noticed on Upwork — but only if you build it right.

Here’s where to look inside the Barefoot Consultants platform:

• Freelancer Membership Area

  Log into BarefootConsultants.com, head to the Members Login, and scroll down to the Freelancer Membership section.
  

• Replay Library

  That’s your treasure chest. Every Tuesday Night Call replay is archived there — over 240 sessions. Use the Webinar Playbacks section to browse, or better yet, use the search trick: CTRL+F (Windows) or Command+F (Mac). 

  • Type “Project” and you’ll instantly see all the Project Catalog sessions we’ve done (including full replays, transcripts, and worksheets).
    

• Project Catalog Deep Dives

  We’ve run at least two full trainings on Project Catalogs (Part 1 and Part 2), showing you exactly how to design, price, and present your offers so they stand out.

👉 Pro Tip from Winton & Heidi: Don’t just watch the sessions — skim the transcripts. 

They’re timestamped, so you can jump right to the sections on pricing, structuring packages, or positioning yourself for the type of clients you want.

And remember — this library isn’t just about Project Catalogs. 

If you’re tackling proposals, profiles, or portfolios, the same search trick will surface 30+ trainings you can dig into right away.

In other words: no waiting until the next Tuesday call to get moving. You’ve got the answers at your fingertips.

CASE STUDY

✍️ Case Study: A Starter-Job Proposal Makeover in Action

On this week’s call, Winton walked through a real proposal submitted by one of our Barefoot Consultants members. 

It was a “starter job” — the kind of small win that builds confidence and gets you moving. 

Here are three lessons from that live edit you can apply to your own proposals right away:

1. Start with Punch, Not Politeness

Skip the stiff openers like “To Whom It May Concern.” Instead, use a warm, conversational greeting — even “Good morning” works. 

And in that very first line, lead with enthusiasm about the client’s project. Example: “I love helping clients streamline their lead generation process!” That kind of energy is magnetic.

2. Make It About Them, Not You

The fastest way to lose a client is to start every sentence with “I.” 
Instead, frame your experience around what it means for them. Swap “I bring proven expertise in…” for “My projects have included…” and connect it directly to the results they’re looking for. 

Remember: every sentence should make them want to read the next.

3. Close with Confidence (Not Courtesy)

Forget “Sincerely” or “Regards,” your closing is prime real estate. Use it to show momentum and invite action.
Example: “Looking forward to working with you on this — let’s get it off your to-do list and onto mine. Makes sense?” 

That little question at the end is a Jedi mind trick — clients can’t resist answering it.

🔑 Big Picture: Your proposal is a sales tool, not a cover letter. 

Keep it client-focused, full of energy, and easy to scan. 

And once you’ve polished one, you’ve got a template you can reuse and adapt for the next job — saving time and winning more work.

Download Winton’s Final Rewritten Proposal :

🎉 After Party Recap: Laughter, Learning, but No Winner This Time…

🎉 This week’s After Party was one for the books! 

We had a blast swapping stories, asking each other freelance questions, and diving deeper into the AI tips Winton shared on the Tuesday Night Call. 

One highlight? Testing out a brand-new quiz format that had us laughing so hard, but we couldn’t crown a winner because all the answers were #1 — so technically, everyone won.

The best part of the After Party is how real it gets: lively conversations, practical advice you can actually use in your business, and the chance to hear what other Barefoot Consultants are trying out. 

You always walk away with at least one idea you can apply immediately.

👉 Don’t miss the next one! The After Party happens on the last Tuesday of each month — which means our next get-together is at the end of October. 

CLICK HERE to sign up now, save your spot, and join us for another round of fun, learning, and maybe even a new quiz format (with an actual winner this time!).

🌍 Fast Track Your Future:
Panama & Rome Await

Big news on the horizon: the next International Living events are lining up, and they’re worth circling on your calendar.

First stop: Fast Track Panama. If you’ve never been, this is the perfect gateway event — a chance to immerse yourself in the energy, explore new opportunities, and connect with people who are making portable income a reality. It’s always one of the most popular gatherings for a reason.

Fast Track Panama

March 20^th – 22^nd, 2026 Panama City, Panama

Winton Workshop: Friday, March 20^th, time TBD

REGISTER FOR PANAMA

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Then comes the showstopper: Fast Track Europe in Rome. Think ancient streets, world-class cuisine, and a gathering of like-minded adventurers exploring how to build a life of freedom abroad. 

🌿Winton even used the Rome trip as a live case study in our Tuesday Night Call. He went through how AI can help plan a trip that blends business, lifestyle, and adventure. (Scroll back up to find the download)

Fast Track Europe

April 10^th  - 12^th , 2026 Sheraton Rome Parco de' Medici, Rome, Italy

Winton Workshop: Friday, April 10th , time TBD

REGISTER FOR EUROPE

—————

These events aren’t just about information. They’re about transformation. 

And whether your first stop is Panama or Rome, the experience will fuel your vision for what portable income can unlock.👉 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.