Greetings Portable Income Earner!

If you thought this week’s call had energy — wait till you see what’s coming tonight!

We’ll be diving into Project Management 2.0: Finding Your Hidden Income Superpower (Part Two) — the follow-up to a session that had more audience participation than we’ve ever had! 

We’ll pick up where we left off and go even deeper into how to turn your everyday skills into consistent, portable income. 

If you’ve ever organized a fundraiser, run a home remodel, managed an event, or kept your family schedule running like a mini corporation — you’ve already done project management. Now, it’s time to get paid for it.

👀 Don’t miss it! If you haven’t attended before, REGISTER NOW

This last week’s session was a masterclass in recognizing that you don’t need a certification to start managing projects on Upwork. You’ve been doing it your whole life — you just called it “work.”

From bake sales to theater productions, from wellness centers to community redevelopment — you all shared examples that proved one point loud and clear: experience translates. 

Whether you’ve managed timelines, coordinated people, or juggled moving parts, those skills have value in the freelance marketplace right now.

We also explored how to:

• 🎯 Find and filter the right jobs using keywords like project coordinator, operations support, or virtual PM
  

• 🧭 Start small and strategic, focusing on entry-level projects under $500 to build fast reviews and momentum
  

• 🤝 Target clients who’ve hired at least 10 freelancers — the ones who understand how Upwork works and will value your expertise
  

• 🚀 Deliver with delight — because the way you communicate and close a project often determines your star rating

And we talked about the real project management tools — not the software names (Trello, Asana, Monday, ClickUp), but the mindset: staying organized, communicating clearly, and taking action over perfection.

Next week, we’ll continue building on that momentum. 

You’ll see real proposal examples using the 7-Element Framework — the one that helps clients say yes faster. 

So bring your curiosity, your coffee, and your examples — this next one is going to be packed with aha moments (and probably a few more laughs).

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

JOB OF THE WEEK

🕵️‍♀️ Job of the Week: Mystery Shopper with a Twist

Shared by BC member Judy C, this one had us all laughing — and learning.

Imagine getting paid to fail a test.

That’s right — a company actually hires freelancers to go into certification testing centers across the U.S. and “mystery shop” their security systems. 

Your job? Try to sneak in a phone or make other security breaches, see if they catch you, and then file a short report afterward.

As Winton put it, it’s “a very interesting kind of use of the whole mystery shopping thing,” and some versions of this job have paid as much as $240 for just a few hours’ work. 

Others, like the one Judy spotted, come in lower — but it’s a perfect reminder that unusual projects can lead to unexpected income.

These gigs usually appear under “mystery shopper” on Upwork, and while they’re not ideal starter jobs (since you have to go onsite), they’re a fun example of how creative freelancing can get.

💡Takeaway: Stay curious, keep scanning those listings, and don’t be afraid to look twice at a job that makes you laugh — it might just be a hidden gem.

🌍 Workshops Worth Waiting For

Big things are on the horizon!

The Portable Income Kickoff Accelerator with Winton and John Canada is gearing up for its next live cohort in January—and you can get on the waitlist TODAY!

This six-week workshop is designed to help you land your first two starter jobs on Upwork and earn your Job Success Score—guaranteed. 

It’s live, hands-on, and fills fast, so click below to reserve your spot early.

👉 Join the Portable Income Kickoff Accelerator Waitlist

Coming next week: the waitlist link for Dr. Rao’s 50+ Energy & Focus Workshop, another January session to start your year with clarity and momentum.

✈️ And if travel is on your radar for 2026…

Winton and his team of coaches will be joining International Living at their upcoming conferences—Panama City in March and Rome in April—where we’ll be sharing more about building portable income from anywhere.

Get on the list, plan your next step, and keep your momentum rolling into the new year.

🎉 The After Party Returns — Tuesday, November 25

Real talk. Real wins. Real fun.
You just have to come to the After Party!

Where else can you find the Freelance Feud, a man with a croissant for a hand, and Winton handing out virtual strawberries — all while learning how to land more Upwork jobs and laugh about AI’s latest quirks?

This month’s Barefoot Consultants After Party happens right after the Tuesday Night Call on November 25, and it’s your chance to:

💬 Swap stories and strategies with other Portable Income Earners

🤖 See how freelancers are using AI to work smarter (and laugh harder)

🎯 Join Freelance Feud Round 11 — new questions, new prizes, same fast-paced fun

💡 Ask Winton anything — from mindset to money to momentum

This hour always fills up with laughs, breakthroughs, and good company — so grab your seat early!

🗓️ Make sure you’re registered and mark your calendar:  Tuesday, November 25 — right after the Tuesday Night Call.

Grab your spot, join the conversation, and be part of the laughter, learning, and lightning-round energy.