Greetings Freelancers!

Exciting news: I’m coming to you unplugged next week—straight from Portland, Oregon.

Between delivering three sessions at International Living’s Ultimate Go Overseas Bootcamp and connecting with hundreds of people chasing their dream lifestyle, I’ll be bringing the highlights directly to you on our Tuesday Night Call.

Here’s what you’ll get when you join me live:

• Insider stories & takeaways from conversations with freelancers, expats, and entrepreneurs at the conference.

• Fresh strategies for running your business from the road—what’s changed since the pandemic, and how to use it to your advantage.

• A live Q&A where I’ll share what’s working right now (and answer your burning questions on the spot).

This is one not to miss. It’s rare I get to combine the energy of an in-person conference with the intimacy of our live coaching calls—but next week, you’ll get both.

👉 Mark your calendar. Be there live. Bring your questions.

Register now (if you haven’t attended yet this year)

Call Recap:
Proposal Pitfalls and Winning Proposals:
What We Learned

This week’s call was equal parts comedy show and masterclass. Heidi and I walked through some real proposal “don’ts” that made us laugh (and cringe)—from the “I’m New” apology proposal to the “Consider it done” three-liner, and even one that offered to work for free (a big no-no under Upwork’s terms of service).

The lesson? Clients aren’t looking for excuses or gimmicks. They want clarity, confidence, and proof you’ve actually read their job description and can deliver the results they’re requesting.

On the flip side, we looked at winning proposals—ones that start with a warm, personal greeting, use playback language from the client’s post, and frame your skills as their benefit (not just “I, I, I”). 

A few small tweaks like shifting from “I pride myself on attention to detail” to “My attention to detail means you’ll get error-free copy” can completely change how a client feels about hiring you.

Two big takeaways:

• Don’t apologize for being new. Let your skills and samples do the talking.

• Make it about them, not you. Use “you” and “your” more than “I” and “me.”
  

• At the end of the day, your proposal doesn’t have to be perfect—it just has to be better than the next best one. That’s how you win jobs, build stars on your profile, and keep moving forward.

Until next week!

Winton

QUESTION OF THE WEEK

❓ Off-Platform Work Explained: Avoid Costly Mistakes

This week, we tackled a two-part question that comes up often:
What happens if a client contacts you directly? And how do you handle invoicing for off-platform work?

Here’s the key distinction:

• If you met the client through Upwork, you must continue working with them on the platform for two years. That’s part of Upwork’s terms of service.

• If you take the relationship off-platform without a buyout, you risk losing your entire profile, history, and Job Success Score—something no one wants after all the effort it takes to build credibility.

But if you meet a client outside of Upwork—at the grocery store, on LinkedIn, or through your network—that work is fair game to handle directly.

Payment options:

• PayPal remains the most widely used and reliable tool for invoicing off-platform work. It offers detailed templates for hourly and fixed-rate jobs and allows you to attach terms and conditions.

• Wise (formerly TransferWise) can be cheaper for international payments, but some freelancers report hiccups with account rules and reinstatements.
  

  Pro Tip: If you and a client you met on Upwork want to work together outside the platform on a bigger project (for example, commission-based arrangements or high hourly rates), Upwork offers a $2,500 contract buyout. Once that fee is paid, you can work together freely off-platform without risk.

➡️ Bottom line: Stay in integrity with Upwork’s system. Build your portable income business the right way, and use off-platform invoicing only when the client relationship didn’t originate on Upwork.

✈️ We’re Here in Portland! Let’s Connect

This weekend 👉 August 29–September 1 we’re at International Living’s Ultimate Go Overseas Bootcamp 2025—their only U.S.-based 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. Whether you’re dreaming of Portugal, Mexico, Costa Rica—or still deciding your perfect destination—this is where ideas turn into action.

If you’re in Portland with us this week—make sure to stop by our Friday Workshop, our booth, or one of our breakout sessions. We’d love to catch up in person and meet you while we’re here!

If you’re local, come down to the conference and say hi—we love meeting our Barefoot Consultants members face-to-face. 

🎉 After Party Highlights: More Q&A, plus Travel Talk

If you’ve never stayed for the once-a-month after party… you’re missing half the magic.

This month’s session was packed with laughs, real talk, and some seriously sharp freelancing insights. 

🌍 We took another mini world tour—this time through Ted in Uraguay…chatting about what it’s like working remotely from a different country, adjusting to a new culture, and staying productive while living the expat dream. So cool!

And then came the After Party Quiz…

Let’s just say it lived up to its reputation…again! Brand new Barefoot Consultants member, Roxi B. walked away with the bragging rights! Gotta play to win! Congratulations Roxi!

*After Parties happen the last Tuesday of every month, immediately after the Tuesday Night Call (TNC). Get it on your calendar, and register here if this will be your first!