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- Real Success Stories from Portable Income Earners 50+
Real Success Stories from Portable Income Earners 50+
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Greetings Portable Income Earner!
Next Tuesday, we’re celebrating real success stories from our community — simple, real examples from Barefoot Consultant members who turned skills and experience into paid, portable income.
You’ll meet people who got started with zero freelance experience, minimal computer skills and are now earning online like pros.
It’s the most inspiring session of the year — and it’s packed with ideas you can use right away!
Don’t miss it! If you haven’t attended before, REGISTER NOW
Project Catalogs
If you missed this week’s Tuesday Webinar, we explored one of the most powerful (and often overlooked) features on Upwork: the Project Catalog — your instant storefront for pre-packaged services clients can buy right now.
Think of it as your “menu” of ready-to-go offerings, designed for clients who prefer to click and buy instead of posting jobs and waiting for proposals.
We showed examples of project listings that stand out — from 5-star article writers and course builders to digital pet portrait artists — and talked about what makes them work:
Clarity and confidence. Each project gives clients an easy decision — they know exactly what they’ll get, how long it takes, and what it costs.
Smart packaging. Tiered options (Starter, Standard, Advanced) let clients “try before they buy” — and often lead to repeat business.
Reach beyond Upwork. With one link, you can share your Project Catalog on LinkedIn, Facebook, Nextdoor, or even your email signature — letting Upwork handle the payments, contracts, and credit card processing.
Like I mentioned, “It’s like having a $5,000 website — without building one.”
If you haven’t yet created your first Project Catalog, this is your week to try it.
Start with something small, repeatable, and fun — and share your link with us next Tuesday.
You might just be our next success story featured on the call!
Now here’s the news from around the Barefoot Consultants’ world,
FEATURE TOPIC
🧰 Starter Project Ideas: From Audits to Templates That Sell
This week, we unpacked dozens of easy project ideas for your first (or next) Project Catalog listing. Each one is fast to deliver, easy to describe, and perfect for building confidence while getting paid.
You don’t have to reinvent yourself to start freelancing — just repackage what you already know how to do.”
-Winton
✅ Audit Services — Review someone’s website, LinkedIn, or marketing plan and offer 3 quick wins.
✅ Setup & Templates — Spreadsheets, forms, and checklists are gold. Many clients pay for done-for-you organization.
✅ Content Packages — Offer a small blog bundle, social media captions, or polished bios. Use AI to help speed up the drafts.
The magic of these simple projects is momentum: you’ll gain reviews, repeat buyers, and proof that you can deliver.
🧭 Try This: Choose one idea that matches your skill set and create your first Project Catalog this week. Then, share the link during next Tuesday’s call — we’ll celebrate your launch!
🎙️ “The Full-Body Dachshund Dilemma” — Why Project Catalog Pricing Matters
During this week’s discussion, Winton and Heidi couldn’t resist a laugh over one pet portrait seller’s pricing tiers.
“How could you have a dachshund and not want the full body?” Heidi joked. Winton added, “They should probably charge extra — dachshunds are longer!”
What started as a joke turned into a key takeaway: how you structure and price your tiers makes all the difference.
Whether it’s an art commission, spreadsheet setup, or blog-writing package, your “advanced” tier should clearly add more value — not just more time.
🧠 Pro Tip: The more thoughtfully you build your Starter → Standard → Advanced packages, the more clients will naturally choose the middle or top tier.
🌐 Your Network Is Bigger Than You Think: Share Your Project Catalog Outside Upwork
Too many freelancers hide their brilliance inside Upwork — waiting for the perfect client to find them.
This week, Winton shared how he turned his offline network into a source of online work opportunities.
💡 Lesson 1: Share beyond the platform. Post your Project Catalog link on LinkedIn, Facebook, Nextdoor, or in hobby groups related to your niche. (Example: a travel itinerary project in a travel group.)
💡 Lesson 2: Skip the personal website. Winton reminded us that “a Project Catalog is your business site — and it comes with payment, contracts, and credibility built in.”
💡 Lesson 3: Multiply your exposure. Each place you share your link opens new doors — sometimes the best clients come from unexpected circles.
🚀 To Do: Add it to your email signature as a generally worded hyperlink, like “Marketing Audit”.
You might be surprised how fast word spreads!
👉 Book a free 30-minute strategy session with Heidi and walk away with game-changing ideas, tailored to you. No pressure. No fluff. Just traction. | Think You Don’t Have Anything to Offer Online?Coach Heidi would beg to differ—and she’s got the track record to prove it. A UC Berkeley grad and globe-trotting freelancer with 20+ years in marketing, real estate, and business development, Heidi has a knack for spotting profitable skills you didn’t even realize were in your toolkit. From training champion show horses to leading real estate marketing teams, she now helps 50+ professionals spot their most marketable skills and turn past experience into freelance traction—without burnout or starting over. |

✈️ From Furlough to Freedom — A Special Webinar with Winton Churchill & John Meskel
If you’ve ever faced a government furlough, job uncertainty, or simply want more control over your income — this webinar is for you.
Join Winton Churchill and Coach John Meskel on Monday, October 28 at 12 p.m. Eastern for …
From Furlough to Freedom — a live session on transforming government experience into flexible, portable income.
Learn how to turn your hard-earned skills into real opportunities — from consulting to freelancing — and discover how others have already done it.
Hear from two seasoned professionals who have walked this path:
👤 John Meskel – Certified Coach and former U.S. Air Force and Federal Civilian Agency leader with experience in the Department of Energy, Department of the Interior, and the Library of Congress.
👤 Winton Churchill – Founder of Barefoot Consultants and former U.S. Air Force, Department of Energy, NASA, and NOAA collaborator, as well as an Apple, Sun Microsystems, and Oracle executive.
Know someone in government service who needs this?
Forward it to them.
🌍 Plus: Upcoming International Living Conferences
Start planning your 2026 travel — and join Winton & his Team LIVE!
We’ve got a full season ahead — and it’s all designed to keep
your momentum growing.
🇵🇦 Fast Track Panama 📍 Panama City, Panama | 🇮🇹 Fast Track Europe 📍Sheraton Rome, Rome, Italy 🎤 Winton’s Workshop: Friday, April 10 |
🎙️ The After Party — Real Talk, Real Wins
If Tuesday Night Calls are where you learn, the After Party is where you level up.
It’s a live, open-floor conversation where Winton answers any question you’ve got — from proposals to pricing — and members swap stories about what’s actually working for them right now.
You’ll hear fresh insights, laugh a lot, and walk away with at least one idea you can use immediately to grow your Portable Income.
Only about 15 people usually make it… which means you get direct access and personalized feedback.
👉 Make sure you’re registered to join us THIS Tuesday, October 28 for “Freelance Feud Round 10” — for your turn in the spotlight.
⭐️ Until then, |









