The Enhanced Art of Helping People

Welcome Freelancer!

Think you know customer service? Think again. In next week’s session, The AI-Enhanced Art of Helping People—and Getting Paid for It, we’re taking a fresh look at what this field really looks like today—and how you can redefine, reinvent, and excel in a space that’s evolving fast.

You’ll discover:

• Why customer service today isn’t what it was 10—or even 5—years ago

• The most in-demand skills clients are looking for now

• How AI can support and amplify your ability to deliver great service

• And why this might be the perfect freelance lane for your next chapter

If you've ever worked in support, taught others, or just enjoy helping people solve problems—this session is a must. It’s not about phone banks or call centers anymore. It’s about flexible, meaningful work that fits today's world—and your lifestyle.

✨ Join us and see what’s possible in this new era of service.

👉 Register here free. If you registered since early February, you’re good to go! for the next 12 months—no need to update again! 💥

 MISSED THE WEBINAR ON TUESDAY? Here are this week’s golden 💰nuggets from “Getting Paid Faster with Messaging & Milestones”…

Winton broke down how to get paid more smoothly—and sooner—on Upwork by using two powerful (but often misunderstood) tools: milestones and messaging.

He shared how submitting deliverables only through the message system can lead to delays—or worse, no payment—if they aren’t properly attached to the contract. The key? Make sure work is submitted via the “Submit Work for Payment” button inside the milestone structure, not just in a message thread.

He also clarified how to use milestones to:

• Break a project into clear, manageable chunks

• Give the client more confidence and control

• Create regular check-ins that make your work easier to approve—and quicker to pay

Milestones are your best friend for smoother workflows and repeat business.

Winton also elaborated on hourly contracts vs. fixed price, and when to use Upwork’s time tracker (and when not to).

🎯 Bottom line: Use messaging to build trust and clarity—but submit work the right way if you want to get paid without delay

🎥 Get the full replay by logging into your Barefoot Consultants platform.

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

See you next week!

ARTICLE OF THE WEEK

🌍 Should You Freelance Before You Flee the Country? (Asking for a Friend With Suitcases)

This week’s featured article sparked a great conversation on a common question:
 “If I’m planning to move overseas, should I wait to start freelancing?”

The article lays out the pros and cons of freelancing at home vs. freelancing abroad—and why starting before you move often sets you up for smoother success. Whether you're relocating full-time or just want the flexibility to travel longer (like many of us do!), the piece explores how to make freelancing work for you, wherever you are.

✨ Bonus: The article’s co-author, Patricia Barakat, played a major role in Barefoot’s early beginnings. Back in 2008, she encouraged Winton to give his first ever talk on freelancing abroad—what started as a small idea for a library fundraiser turned into a packed house and the spark that launched a movement.

READ THE ARTICLE IN FULL

📚 This article (and dozens more like it) is available in your Barefoot Consultants Platform—go have a read and see why this topic still hits home today.

QUESTION OF THE WEEK

Winton tackled this hot-button topic head-on by showing us exactly how to get clarity—by asking AI directly. He demonstrated how ChatGPT can explain its own copyright policies and gave a simple rule of thumb: if you generate original content with AI (not copying copyrighted sources), you can claim ownership and even publish or sell it under your name.

💬 Winton’s tip: Ask ChatGPT itself: "Do I own the copyright to the content I generate here?" It will walk you through what’s allowed, what to avoid, and how to stay on the right side of the rules.

It was a smart reminder that when in doubt, ask the tool you’re using—and let it help guide your process.

JOB OF THE WEEK

For Pet Lovers with Opinions!

This week’s featured job was a fun one—testing cat and dog toys for pay! The client’s looking for pet owners aged 50+ to give honest feedback (and yes, you'll probably need to snap a pic of your furry friend enjoying the goods 🐶🐱).

But this wasn’t just about cute toys—it was a great example of how to vet a job and client quickly:
✔️ Payment verified
✔️ 4.5+ star rating
✔️ Clear communication noted in reviews
✔️ Organized job description with usable proposal phrases like “passion for pets” and “detailed feedback”

This client hasn’t been on Upwork long, but their reviews are solid and the hire rate is strong. If you're building your early wins and 5-star ratings, this is exactly the kind of low-risk, high-fun gig that helps get momentum.

👉 Tip: Want your job find featured next week? Send the job link (not a screenshot!) to: [email protected]

📆 Mark your calendar and join us on May 27 —that’s next Tuesday! — right after the Tuesday Night Call for
FREELANCE FEUD!

Whether you played last time or are 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! 🏆

✅ Fun, fast-paced freelancing trivia—test your knowledge and learn as you go!

✅ A chance to win and claim your spot on the leaderboard

✅ Lively discussions, insider tips, and great company

Not getting 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!

Challenge yourself, connect with other freelancers, and have a blast while picking up valuable freelancing insights!

See you 👀 Tuesday, May 27 @ 8pmCDT