Greetings Portable Income Earner!

🚀 We’re not changing direction — we’re accelerating.

Next Tuesday, we’ll build on the foundation we started this week and dive into Build Fast. Grow Smart: The Three Fastest Ways to Grow Your Freelance Business.

You’ll discover how consulting, coaching, and content development can each create immediate traction — and how combining them strategically can turn your freelancing into a steady, scalable Portable Income stream.

This session is all about momentum and mastery — how to move from starter jobs into work that builds both confidence and consistency.

If you’ve been waiting to feel that breakthrough moment in your business… this is the one to catch.

Don’t miss it —If this will be your first time attending, Register now

This week’s Tuesday Night Call took us on a bit of a rollercoaster ride — literally and figuratively — as we dug into how to build freelance momentum fast by focusing on starter jobs.

It’s always inspiring to see how small, simple projects can completely change your trajectory on Upwork. These “starter jobs” — things like beta reading, short transcription, or quick proofreading gigs — are more than just $5–$15 tasks. They’re the gateway to confidence, credibility, and visibility on the platform.

Here are a few takeaways that came up during the call:

• Momentum matters. Getting that first job (even a small one) signals to the algorithm that you’re serious — and it starts pushing your profile higher.

• Confidence compounds. Each completed job builds your reputation and your rhythm, which leads to more—and better—offers.

• Clients are watching. Many smart clients use low-cost starter jobs to “test” freelancers before awarding bigger work. Treat every $10 project like it’s a $1,000 audition.

We shared real examples from our members — Sarah’s $10 beta-read that turned into a novel series, and Emma’s $8 data-entry task that grew into a $300-a-week contract.

These stories are proof that small starts can lead to big wins when you approach them the right way.

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

FEATURE TOPIC

🌟 Starter Jobs: The Smart Way to Start Strong

If you’re waiting to “feel ready” before landing your first Upwork job — stop waiting. 

Small, simple starter jobs are the fastest way to build momentum. 

These $5–$15 projects might look tiny, but they do three big things: they build confidence, collect feedback, and trigger the algorithm to show your profile to more clients.

Think of each one as a seed. The first sprout may look small, but soon you’ll have a full garden of steady work. 

Many of our members started with one short gig — proofreading, beta reading, data cleanup — and turned it into repeat clients and long-term contracts.

Takeaway: Don’t wait for the “perfect” job. Apply for small ones now. Every completed job tells Upwork, this freelancer delivers — and it will start sending you more.

BONUS DOWNLOAD: Proposal Templates That Win Jobs 

This week, Winton walked everyone through two proposal templates — one short, one detailed — that you can use right now. Both are built to help you sound confident, professional, and client-focused without falling into the “I-me-my” trap that sinks most proposals.

You’ll see where to personalize, where to keep it brief, and how to end with a punch — “Let’s get this off your to-do list and onto mine.” It’s one of our favorites, because it works.

Takeaway: Use these templates as your base. Modify them 20–30% for each job, and you’ll not only sound polished — you’ll save time and win more work.

🚀 The Confidence Cycle: Small Jobs → Big Results

Momentum is magic — Every small project builds your confidence, grows your reputation, and opens the door to higher-paying jobs.

The formula is simple: easy wins → positive reviews → visibility → bigger wins. One of our members turned an $8 transcription into a weekly $300 retainer. That’s not luck — that’s leverage.

Takeaway: Start where you are. Focus on finishing, not perfection. Each small win compounds into authority, income, and freedom — and that’s what a Portable Income business is all about.

✈️ The Adventure (and Opportunity) Ahead:
International Living 2026

The next few months are packed with inspiration, connection, and momentum. First stop: Fast Track Panama, March 20–22, 2026. 

If you’ve never been, this is the perfect gateway event — a chance to immerse yourself in the energy, explore new opportunities, and connect with people who are making portable income a reality. Winton will be leading a special workshop on Friday, March 20th — don’t miss it!

Then comes the showstopper: Fast Track Europe in Rome, April 10–12, 2026. Think ancient streets, world-class cuisine, and a gathering of like-minded adventurers exploring how to build a life of freedom abroad. 

Winton’s Rome Workshop kicks off on Friday, April 10th — a perfect start to an unforgettable weekend.

And there’s more coming… starting next week, Barefoot Consultants will be adding our own lineup of workshops to the calendar — designed to help you grow faster, earn smarter, and take your portable income skills to the next level. 

Keep an eye on next Tuesday’s call and this newsletter for details and sign-ups.

🎉 Don’t Miss the After Party: Freelance Feud, Round 10!

The month isn’t complete without our favorite community tradition — the Barefoot After Party. On October 28th at 8:00 PM (Central time, USA), immediately following our Tuesday Night Call, we’ll gather for Round 10 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 even 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.

See you October 28!