Greetings Portable Income Earner!

Next week, we’re diving into a topic that I know has been on many minds: how AI can actually help you — right now — in building portable income.

I’ll be sharing some simple, practical ways to use AI tools to make your freelancing faster, sharper, and more competitive. 

Think of AI not as something futuristic, but as your on-demand tutor, ready to help you learn a new skill, draft better proposals, or even test-drive ideas for services you can offer.

You don’t want to miss this one. Register now

This week’s call was a perfect setup for that. Heidi and I tackled the “17 Myths of Upwork,” those nagging misconceptions that can definitely hold people back. 

We heard questions from members who wondered if sending out a handful of proposals without hearing back meant they were doing something wrong, or if they needed to wait until their profile was “perfect” before ever applying.

Those are real concerns — but they’re myths. Once you see how the system actually works, the path forward looks a lot less intimidating.

So join me next Tuesday for this practical AI session. Bring your questions (and your curiosity) and let's turn AI from a buzzword into a business tool.

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

See you next week!

MYTH BUSTING

🚫 Myth Spotlight: “Every Proposal Should Win”

One of the biggest stumbling blocks is the belief that if you’re qualified, you should win most of the jobs you apply for. 

Reality: it often takes 10–15 proposals to land that first contract.

Silence from clients isn’t rejection — it’s just part of the process. The key is persistence, not perfection. 

As Winton always says: “Don’t waste time wondering why. Just move on to the next proposal.”

💵 Myth Spotlight: “First Job Equals High Pay”

We’ve seen too many professionals aim at a $3,000 project right out of the gate — only to get discouraged. The truth is, starter jobs matter. 

That $5–$15 gig may feel beneath your experience, but it can lead to trust, reviews, and eventually $5,000-plus projects. 

Think of it like Heidi said: pulling on a tiny thread that can unravel a much bigger sweater.

🕒 Myth Spotlight: “Profiles Must Be Perfect Before Applying”

Don’t fall into the trap of endlessly polishing your profile before bidding. 

Yes, fill in all the sections — but remember, profiles evolve. 

Client feedback and early jobs will shape what resonates most. Start solid, then refine as you go.

Watch the full session here…

QUESTION OF THE WEEK

✍️ Question from the Community:
Withdrawing Proposals

Barefoot Consultants member Mark asked:

“If a proposal was never viewed, can it be pulled back so you get your Connects refunded?”

Answer: Not really. You’ll only see Connects returned if the client cancels the job or violates Upwork’s rules. 

The better strategy? Leave your proposal in place. Upwork will archive it once the job closes — no extra effort from you required.

ARTICLE OF THE WEEK

🌍 Hybrid Freelancing: The Best of Both Worlds

Winton also touched on hybrid freelancing — blending Upwork projects with other income streams like coaching, consulting, or teaching. 

Many of our members find this creates stability and variety while they grow their freelance practice.

For example:

if you’re a writer, maybe you take editing projects on Upwork while offering a short online workshop in your niche. 

If you’re a consultant, maybe you supplement Upwork jobs with a coaching package. 

The point is: freelancing doesn’t have to be “all or nothing.” Hybrid models smooth out the income roller coaster and let you test different ways of working.

✈️ Looking Ahead: IL 2026

We’ll be at several IL conferences in 2026, and we’d love to see you there:

March – Fast-Track Panama

April – Rome (first time ever!)

Later in the year – More destinations to come.

These events are where the “someday” dream of portable income becomes “today.” Nothing replaces the energy of being in a room full of people all moving toward similar goals!

🎉 Freelance Feud After Party – September 30

Our monthly after-party is always a highlight. Join us for games, laughter, and a few freelancing lessons slipped in along the way. If you haven’t registered yet, do it once and you’re set for the rest of the year.

CLICK HERE TO REGISTER ✅