Welcome Freelancer!

Next week, we’re taking a deeper dive into writing proposals that land the jobs you really want!

I’ll walk you through how to spot high-value opportunities, understand exactly what top clients are looking for, and tailor your proposal to match—using my proven seven-element strategy that has worked for hundreds of freelancers.

We’ll cover how to position yourself to outshine the competition and how to leverage a strong Job Success Score into bigger, better-paying contracts.

If you’re ready to move from the corral to the open range—this is the session that shows you how.

Register now and don’t miss out!

This week’s call recap: 🧠 Fast-tracking Your Way to Five Stars —My Simple Formula

On this week’s call, we covered what happens when most people join Upwork…They shoot for the $1,000+ gigs right away. 

I get it—that’s where the money is. But the truth is, the fastest way to get to those jobs is through two tiny “starter” jobs. We’re talking $5, $10, maybe $20… and no, you don’t do them for the money. 

You do them to unlock Upwork’s “penalty box” and get the platform’s algorithm working for you—better job recommendations, more visibility, and access to higher-quality clients.

In our session, I showed how to find these quick, easy-to-complete jobs (think mystery shopping, surveys, site testing) and how to write ultra-short, confident proposals that win them. 

Your goal here isn’t to impress the client with how clever you are—it’s to deliver exactly what they ask for, on time or early, with zero complications. 

That’s how you earn 5-star reviews.

One standout question: “Can I name-drop a well-known client or company I worked with through a past employer?” Absolutely. Recognition builds instant trust.

If you’ve been struggling to get traction on Upwork, this strategy will change the game for you. 

I even walked through a complete example proposal, line-by-line in the replay—use it, duplicate it, and get yourself out of the corral and run with the herd.

🎥 Watch the replay… And don’t forget to mark your calendar for next Tuesday!

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

See you next week!

QUESTION OF THE WEEK

Should You Bid on Older Jobs?

This question pops up a lot, and the short answer—according to Winton—is “it depends.” Some jobs get snapped up in a day! 

Others, especially high-ticket or specialized ones, may sit for weeks (or even a year) while the client waits for the perfect fit.

Many buyers intentionally let proposals pile up so they can review them all in one sitting.

And sometimes, as Heidi pointed out, life just happens—projects get delayed, priorities shift, and that long-forgotten posting suddenly becomes active again.

Bottom line: never delete a promising job. The system will archive it if it closes, but if it’s still there, you can still win it—even months later.

For starter jobs, though, it’s more like how Tom Cruise describes a Hollywood “cattle call”: dozens of people vying for the same role, and timing is sometimes everything.

✈️ Just 2 Weeks Away:
Come to Portland with Us!

There are still spots available for Winton’s Workshop on Friday, August 29th where you can gain in-depth insights into how to utilize the knowledge you already have to create your portable income lifestyle.

From August 30 to September 1, we’ll be at International Living’s Ultimate Go Overseas Bootcamp 2025—their only U.S.-based event this year—and we’d love for you to join us!

This 3-day, high-impact event is packed with practical advice, expert guidance, and real connections to help fast-track your dream of living or working abroad.

Whether you’re curious about Portugal, Mexico, Costa Rica, or beyond—this is where the “someday” plan starts getting real.

🌍 800+ attendees
🧭 3 days of insider info
🤝 1 chance to connect in person

We’ll be there. Will you?
👉 August 30–September 1 | Portland, Oregon

🎉 Join us for August’s After-Party on the last Tuesday of the Month, directly following the Tuesday Night Call.

Whether you played last month or you’re joining for the first time, this is your chance to challenge yourself, connect with other freelancers, and have a blast while picking up valuable freelancing insights!

Looking for the join link? REGISTER HERE You only need to register once, to automatically get the link for the rest of the year—no need to update again!