Greetings Portable Income Earner!

Before we wrap up the year, I want to give you a heads-up about next week’s Tuesday Night Call, because it’s a big one — and it’s something every freelancer eventually runs into:

How to Navigate Your Client’s AI Preferences

More and more job posts on Upwork now say “No AI” or “AI use must be disclosed.”

But what does that actually mean? How do clients know whether AI was used?

And how do you protect yourself while still leveraging the tools that make you faster, better, and more competitive?

Next week, we’ll be breaking this down clearly and practically:

• What clients really mean when they say “no AI”
  

• How AI-detection tools work (and don’t work)
  

• Why AI gets less detectable every month
  

• Why avoiding AI completely is the modern equivalent of selling buggy whips when the car has just arrived

Heidi shared the perfect reminder on the call this week: when she first started, she resisted AI — not because she couldn’t learn it, but because the whole thing felt really intimidating. 

If you relate to that, you’re not alone. But once you understand how it works (and how clients think about it), you stop feeling hesitant and start feeling confident.

This is going to be a very clarifying session, especially as we move into 2026.

This week’s call was all about “Experience into Evidence: The 3 Portfolio Upgrades Clients Notice.”

Most freelancers on Upwork have plenty of experience, but to the client it can sound vague: “I did this, I did that.” Your portfolio is where that turns into proof.

We walked through three practical upgrades:

1. Turn real projects into clear examples.
   Instead of a blank white box, you want 2–3 strong portfolio items with eye-catching thumbnails (faces, scenes, or simple visuals) and a clean, readable layout. Think “sample of my work,” not “wall of text.”
   

2. Frame the transformation, not just the task.
   Clients don’t just want to know what you did—they want to see the journey: the challenge, what you did about it, and what changed as a result. Your portfolio is the perfect place to tell one or two short, well-chosen stories that show how you help people through real turning points.
   

3. Back up your claims with third-party evidence.
   Articles, press mentions, screenshots of results, or short clips from public videos all help answer the client’s silent question: “Did this really happen?” Even one outside proof source makes your profile feel far more credible.

Bottom line: you don’t need 50 portfolio pieces. You need a small handful that are neat, visual, and evidence-rich—so a client can understand who you are and what you deliver in two or three minutes.

👀 Don’t miss next week’s call! — If this will be your first time attending, click here to REGISTER NOW

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

THIS WEEK’S FEATURE - Part 1

Your Story Is Your Advantage: The Simple Shift That Makes Clients Believe You Can Help Them

One of the biggest surprises for new freelancers is realizing how little clients understand about your past jobs, titles, or industries. If you simply write, “I managed complex projects,” they have no idea what that actually means.

But when you turn a single real experience into a small, well-framed story, everything changes.

That’s exactly what happened with Robert, one of our members. On paper, he was a dancer, gymnast, actor, theatre director, and coach. Impressive? Sure.

Clear and compelling? Not really.

But when he shared the story of auditioning for Cats—the months of callbacks, the disappointment of being cast as a swing dancer instead of a lead, the eventual realization that learning eight roles ultimately shaped his entire career—the transformation became obvious:

• He handled pressure.

• He adapted quickly.

• He built relationships across a whole cast.

• He learned to navigate disappointment and turn it into opportunity.

Those are the exact traits clients hire for.
And none of that would have surfaced by listing job titles or bullet points.

Your takeaway:
Pick one meaningful experience from your last decade—something that changed how you work, think, or solve problems. Write it as:

Challenge → Approach → Outcome → What You Learned

Then turn it into a short article-style portfolio item with a clean layout, a title, a subtitle, and one compelling image.

This is how you go from “Here’s what I did” to “Here’s why you can trust me with your project.”

Download Infographic: The 3 Portfolio Strategies That Make Clients Say “Yes” Faster

If you want more clients choosing you in 2025, this is the cheat sheet to keep by your side.

These 3 proven portfolio upgrades (straight from this week’s TNC) help clients trust you faster, understand your value quicker, and feel confident hitting “Yes” on your proposal.

This one-page guide walks you through what buyers look for in the first 3 seconds — and how your portfolio can quietly do the selling for you. 

Think of it as having Winton and Heidi sitting next to you, pointing out exactly what to fix first.

👉 Download your “Experience into Evidence” Infographic

 Use it this week. Small upgrades here = big wins later.

THIS WEEK’S FEATURE - Part 2

⭐Proof Beats Promises: The Easiest Way to Add Instant Credibility to Your Portfolio

Freelancers often tell us, “I don’t know how to show my value—I’ve never created formal ‘work samples.’”

Great news: you don’t need them.

What truly builds trust isn’t polished marketing material…it’s third-party evidence. Anything OUTSIDE of your own words that signals, “Yes, this really happened.”

During the call, we looked at how Robert used:

• A short clip from LA Confidential showcasing his appearance in the film

• Press coverage from NPR about a million-dollar arts grant he helped secure

• A PDF of a newspaper profile written about his work

• Photos from backstage rehearsals and theater productions

None of this required new work. None of it required design skills.

It simply required pulling meaningful proof from his past—and presenting it neatly.

Why this works:
Clients don’t just want to hear your story.
They want evidence that other people noticed it too.

And you probably have more than you think:

• A mention in a company newsletter

• A screenshot of an award or recognition

• A public YouTube video about an organization you contributed to

• A press release, blog post, or article involving your project

• A testimonial tucked inside an old email

Turn those into PDFs, add a short description (100–150 words), and attach them to your portfolio.

Even one strong piece of third-party proof can make you stand out instantly—because while most freelancers make claims, very few show evidence.

📅 Workshop Wait Lists Are Now Open

We shared the upcoming 2026 workshop lineup during the call, and wait lists jumped immediately:

Both workshops will open first to those on the waitlist, then to members, and finally to the general public — so if you’re thinking of joining, get your name in early before we hit capacity again!

✨ ✨ ✨ ✨ ✨ 

And if you have dreams of travel… Join Us at the International Living Conferences — Panama & Rome

✈️ Two Unforgettable Destinations. One Incredible Experience.

If you’ve ever dreamed of exploring life overseas — or just love the idea of learning and connecting in a stunning location — the International Living events are the perfect place to do it.

🌴 Panama (March)

A vibrant coastal city, a harbor with 20-foot tides, and a hotel overlooking it all. You’ll meet like-minded adventurers, hear life-changing insights, and get a fresh perspective on what “portable income” really makes possible.

🇮🇹 Rome (April)

IL’s first-ever Rome conference — and it’s going to be spectacular. History, food, architecture… and conversations that could open doors you didn’t even know existed.

Many of our long-term members first met Winton (and us!) at an IL event. It’s truly one of the best ways to learn, connect, explore — and imagine what’s next.

👉 Click the links below and join us in Panama or Rome… or both. Life’s too short not to.👀These fill fast — especially Panama and Rome, where seating is capped.

After Party & Tuesday Night Call will be combined on December 30th, for the Holiday, just as we did at Thanksgiving

This will be a live Q&A and roundtable-style session, more interactive than usual, with plenty of opportunity to ask your questions and share what’s working for you. And yes, rumor has it there may even be a little quiz — and maybe even a prize — to keep things fun.