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Grateful, Growing, and Getting Paid This Week in Portable Income
A holiday-sized dose of clarity + your downloadable superpower list
Winton Churchill & Heidi Craig
November 28, 2025
Greetings Portable Income Earner!
This week we hosted our “Thanksgiving Unplugged” session on the Tuesday Night Call— a lighter, more interactive hour where the community steered the conversation. Folks joined from Mexico, Aspen, Honduras, Uruguay, Panama, Chicago, Missouri, Georgia, and beyond.
Our call opened with a poll about what you wanted to discuss and a surprise: 62% of you voted for Tools, Tactics & AI Tips, followed closely by the Wild Card Jar — which led to some of the funniest and most useful conversations we’ve had all year.
From tax myths and 1099’s to Nano-Banana AI image tools to what you’re grateful for this season, we covered a lot of ground.
If you missed it, below are the pieces we believe will matter most to your portable-income journey this week.
Happy Thanksgiving — and thank you for being part of this community that continues to learn, laugh, and lift each other up.
👀 Don’t miss next week’s call! — If this will be your first time attending, REGISTER NOW
Now here’s the news from the Barefoot Consultants’ world,
✨ This Week’s Moments Worth Sharing
Instead of a single “big takeaway,” this week delivered a handful of small-but-mighty insights — the kind that stick with you because they’re so human:
• Most unexpected Upwork discovery:
A weekend-long ghostwriting project with… zero instructions. (We all agreed: red flag + comedy gold.)
• Skill someone forgot they had:
Scriptwriting — rediscovered live on the call.
• Favorite AI party trick:
Turning friends into fictional characters for birthday cards. (10/10 would recommend.)
• Community gratitude themes:
Health. Clean water. Courage. Fresh starts. Travel. Grandkids. A dog who finally stopped barking.
And — sweetest of all — each other.
• Biggest portable-income win of the night:
Another wave of members hit their Job Success Score this week, some in record time.
It was a beautiful reminder that momentum doesn’t always look dramatic — sometimes it’s one small spark, one tiny win, one brave question at a time.
🔥 Featured Resource of the Week: Your 13 Superpowers After 50
If you enjoyed the gratitude theme on the call, this week’s free download is the perfect companion:
13 Superpowers of People Over 50
—it’s fast, inspiring, affirming, and a great reminder that you’re not “starting over”… you’re bringing an entire lifetime of advantages to the table.
Inside you’ll find:
Why clients trust mature professionals faster
The emotional intelligence edge no algorithm can touch
Why reliability is now a premium skill
And the quiet strengths you probably overlook in yourself
💥 CLICK THE BUTTON BELOW TO GET THE DOWNLOAD
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🔑 Spotlight: The New Freedom Vault
We officially unveiled the new Freedom Vault this week — expanded, reorganized, and built to help you make progress every week without having to remember where anything is.
Here’s what members told us they wanted (and what we built):
Every Tuesday replay in one place
Clean categories for profiles, proposals, starter jobs, interviews, AI tools, and more
“Cliff notes” summaries so you can skim and get the gold —fast
Timestamps so you can jump straight to what you need
Every checklist, template, cheat sheet, and resource — neatly organized
Early access to workshops and member-only events
If you’ve ever thought:
“What was that thing Winton said we should do two weeks ago…?”
This solves it.
It’s the simplest way to stay connected, stay moving, and stay confident.
📌 Choose your membership…
Monthly or Annual (saves you 37%)
Think you’re “not techy enough” or “starting too late”?My favorite thing in the world is proving you wrong — gently, cheerfully, and with a plan that actually fits your life. I help 50+ professionals uncover the skills they didn’t even realize they had and turn them into portable income… without burnout, overwhelm, or hustle culture nonsense. 👉 Book a free 30-minute session — bring your background, and I’ll show you what’s marketable before we even hang up. |
📅 Workshop Wait Lists Are Now Open
🚀 Portable Income Kickoff Accelerator
Begins January 21st — the signature workshop that helps you jumpstart your Upwork success with the proven Barefoot framework. |
💪 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). |
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 have dreams of travel… 🌍
Join us in person this spring at Fast Track Panama (March 20) or the Rome Conference (April 10) with International Living.
👀These fill fast — especially Panama and Rome, where seating is capped.
Fast Track Panama 📍 Panama City, Panama | Fast Track Europe 📍Sheraton Rome, Rome, Italy 🎤 Winton’s Workshop: Friday, April 10 |
🎯Join us in the Facebook Group! |
