Greetings Portable Income Earner!

If you’ve been spinning your wheels on Upwork… this is the week everything gets easier.

We’ll be taking a deep dive into the best, easiest, fastest job searches you’ve ever seen. 

After months of refining the process, I’m going to walk you through the new, streamlined system for finding the right jobs — the ones that fit your background, your income goals, and your available hours.

As Heidi reminded everyone this week, honing your search skill makes all the difference. 

When you can spot five similar projects quickly, you can write one proposal and lightly adapt it four more times — cutting your time investment and multiplying your odds of landing a client. 

The magic is in finding better jobs faster so submitting proposals takes less time.

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

This week, we continued with Part Two of our Project Management Series, moving from “finding” to “winning and delivering.” 

We started with proposal strategy: how to balance experience-building with income-building. 

If you’re moving into a new area like project management, think of your first few projects as an audition. The goal is to gain traction and reviews — not chase your top hourly rate right out of the gate.

You heard me say it, and it’s worth repeating:

“The secret isn’t luck — it’s consistency. Three to five proposals a week will change everything.”

Heidi then jumped in with a great reminder that refining your search focus makes proposal writing faster. 

When your jobs have a similar theme, one strong proposal becomes five quick submissions. And that’s how you keep your pipeline flowing.

We also looked at what clients actually see when they get proposals — those first 140 characters that can make or break your proposal. Many freelancers waste that space with “Hi, my name is…” or a long introduction. 

Instead, lead with the fit: why your experience matches their needs. Keep it simple, human, and confident.

And finally, we talked about momentum. Freelancing success doesn’t come from big leaps; it comes from steady steps. As Heidi put it perfectly,

“The tortoise wins. Just stick your foot in, one toenail at a time.”

So next Tuesday, we’ll take everything you learned about proposals and delivery — and show you how to find those opportunities faster than ever before.

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

QUESTIONS FROM THE TNC

💬 Real Questions from Real Freelancers

Straight from the Tuesday Night Call — where curiosity meets clarity.

Every week, BC members jump into live Q&A with Winton and Heidi to ask the questions that matter most. 

It’s part of the fun every Tuesday night — honest talk, quick takeaways, and the kind of answers you won’t find in a YouTube tutorial.

Here are a few favorites from this week’s call:

🟢 Q: “What if I have too much experience for a small job?”
 A: Lead with relevance, not your résumé. A five-sentence proposal that connects your experience to this project beats a five-paragraph life story every time. Clients want fit, not volume.

🟢 Q: “Can AI help my profile photo?”
 A: Maybe — but as Winton joked, “Get your bogus photo in before Upwork’s AI gets smarter!”
AI tools can polish your picture, but remember: Upwork still uses that image to match your ID. Authenticity (and good lighting) win every time.

🟢 Q: “How do I know if a client is safe to work with?”
 A: Look for Payment Verified, past hires, and clear instructions. Then relax — Upwork escrow has your back.

🟢 Q: “How do I keep going when I’m not getting quick results?”

A: Think of proposals like seeds — not every one sprouts, but each one teaches you what grows best. The freelancers who win are the ones who stay in motion, tweaking, testing, and trying again. Progress on Upwork is less about luck and more about steady, visible effort.

🎙️ Want your question answered live next time?

👉 [Save Your Seat for the Next Tuesday Night Call]

JOB OF THE WEEK

This week’s Job of the Week came from BC member Kathryn N., who brought us a real conversation starter — a book editing job that seemed promising… at first glance.

The client stats checked all the right boxes:
✅ Payment verified
✅ Over $3,000 spent
✅ 4.5+ star rating
✅ Based in an easy time zone
✅ Over 50% hire rate

“Looks like a great client,” Heidi said — “until you look at the job post itself.”

What did it say?
Just three words: “Book editing job.”

That’s it. No details. No word count. No timeline — except that it “starts today” and somehow needs to finish by the weekend.

As Winton put it,

“They’ll pay you quite a bit of money if they’ve got a deadline… but when there’s no relationship and a two-day turnaround, you just don’t know what you’re walking into.”

Their advice to freelancers:

• Let the client say no — not you. If it looks possible, bid and ask smart questions.
  

• Schedule a call before accepting — preferably on Zoom — to get a feel for their personality and expectations.
  

• If it’s not a fit, bow out early. No harm, no review, and no wasted weekend.

Thanks to Kathryn for finding a great teaching moment!

✈️ New Year, New Opportunities: Workshops & Events You Won’t Want to Miss

We’re kicking off 2026 with two powerhouse workshops and a pair of international adventures — and spots are already filling fast!

🚀 Portable Income Kickoff Accelerator

Begins January 21st — the signature workshop that helps you jumpstart your Upwork success with the proven Barefoot framework.

👉 Join the P.I.K.A waitlist

💪 50+ Energy & Focus Workshop (with Dr. Rao)

Reignite your energy, focus, and productivity — built for freelancers over 50 who want to work smarter (and feel sharper).

👉 Join the 50+Energy waitlist

Both workshops will open first to 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’ve been dreaming bigger… 🌍

Join us in person this spring at Fast Track Panama (March 20) or the Rome Conference (April 10) with International Living. 

Don’t wait until “after the holidays” — these global events fill up quickly too, and once the spots are gone, they’re gone!

🎉 Don’t Miss the After Party: Freelance Feud, Round 11!

The month isn’t complete without our favorite community tradition — the Barefoot After Party.

On November 25th at 8:00 PM (Central time, USA), immediately following our Tuesday Night Call, we’ll gather for Round 11 of Freelance Feud.

If you’ve never joined, imagine a mash-up of Family Feud, freelancer life, and plenty of laughs. 

It’s lighthearted, a little competitive, and the perfect way to cap off the month with your fellow Barefoot members. 

You’ll pick up insights without even realizing it — and walk away with a smile (and maybe bragging rights if you win).

👉 Get registered, bring your quick wit, and get ready for an evening of fun that keeps our community strong and connected.