Hello Portable Income Earner!

Next week, we’re diving into the lighter—but oh-so-important—side of proposals: the do’s and don’ts.

I’ll be sharing some hilarious (but real!) examples of proposals that completely missed the mark, along with the Top 5 Pitfalls to avoid. 

Then, I’ll show you what actually works—with over six winning proposals that landed freelancers solid jobs.

You’ll come away with a crystal-clear sense of how to write a proposal that gets noticed, gets taken seriously, and most importantly—gets you hired.

If you’ve ever wondered what separates the “Oops” from the “Win!!!”—this session is for you.

Register now  and join the fun (and the learning)!

This Week’s Call Recap: Proposals That Land Jobs

When a client posts on Upwork, they’re not window shopping. They’re waiting to see who steps forward with a proposal. 

That’s why I kept saying this week: your proposal is almost always the first impression that matters.

Here’s what I showed you on the call:

• Most proposals fail instantly. Close to 80% are deleted without a second thought because they’re generic cut-and-paste jobs. Clients can see those from a mile away.
  

• The winners are relevant. Strong proposals connect your skills with unique knowledge. It’s not, “I can write about anything,” but, “I’m a veterinarian who understands animal care.” That kind of connection moves you from “1 in 50” to “1 in 5.”
  

• The open matters most. A simple “Hi Bill” plus a sharp, relevant first line puts you in a different league. Remember, you can often find the client’s name in their freelancer feedback.

The key is this: clients aren’t just buying your skill. They’re buying the result that skill creates. Editing is the skill. A successful book is the result. That’s what gets you hired.

Why Be Live?

Reading a recap is helpful, but it’s not the same as being there.

On the call, we laughed through some funny proposals, broke down real examples line by line, and turned your questions into live teaching moments. That’s where the lightbulbs go off—the small shifts that turn a “meh” proposal into a “must-hire.”

Arrive live, and you don’t just get the notes—you get the breakthroughs.

Looking forward to seeing you there!

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

QUESTION OF THE WEEK

“Do I need to keep getting other jobs, or will my Job Success Score roll off?”

Barefoot Consultants member Doug asked: “Do I need to keep getting other jobs, or will my Job Success Score roll off?”

Answer: Great question! Your Job Success Score (JSS) does need some ongoing activity to stay strong—but it’s easier to maintain than you might think. 

The algorithm watches your activity: logins, bids, wins, and completions. Once you’ve earned your JSS through two jobs with two different clients, you don’t need to keep chasing starter jobs every month.

Instead, aim for one job per month—ideally in your own domain, since those tend to pay more and build your credibility. 

If you know you’ll be away (vacation, cruise, etc.), grab a quick starter job before you go. That small step keeps your score fresh, the algorithm happy, and your visibility high.

Bottom line: one job a month keeps your JSS in good shape—no need for 5–10 tiny jobs.

LIVE DEMO

Ever wonder why some freelancers crank out polished proposals quickly while others stall out? 

In this video, Coach Heidi walks you through the exact systematic process she uses herself and teaches her clients, every single time.

This process isn’t about reinventing the wheel—it’s about using the same structure over and over so you:

• ✅ Hit every requirement in the job description

• ✅ Build authentic connection with the client

• ✅ Save time and write more proposals—without sacrificing quality

The result? Faster proposals, stronger structure, and a higher chance of landing the jobs you really want.

👉 Watch this quick demo to see how she set up her proposal document, highlights key client cues, and streamlines the writing process so it becomes almost “fool proof.”

✈️ Next Week in Portland: Don’t Miss It!

It’s almost here! In just days, Winton’s Friday Workshop (Aug 29) will give you the tools to turn the knowledge you already have into your portable income lifestyle. Spots are still open—but they won’t be for long.

Then from August 30–September 1, we’ll be at International Living’s Ultimate Go Overseas Bootcamp 2025—their only U.S. event this year. 

Three packed days of insider guidance, practical strategies, and face-to-face connections designed to fast-track your move toward living or working abroad.

🌍 800+ global-minded attendees
🧭 3 days of insider strategies
🤝 The chance to connect in real life

Whether you’re eyeing Portugal, Mexico, Costa Rica—or a country still on your “someday” list—Portland is where ideas become plans.

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

🎉 Next Week: August After-Party!

Mark your calendar—the After-Party is back next Tuesday,
right after 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.

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