Get Paid Faster with Milestones and Messaging

Turn long gigs into quick-pay milestones

Welcome Freelancer!

Confused about how (and where) to submit your work on Upwork? You’re not alone! 

Next week, we’ll break down how to use milestones and messaging the right way—so your deliverables are clearly tied to the contract, your client knows what’s what, and you get paid without delay. 

We’ll also cover when to use time tracking, how fixed-price protection really works, and why knowing these details can help extend contracts and build trust.

Don’t miss this one—these are the strategies that turn one-time gigs into reliable income.

👉 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 Tuesday’s Call? Here’s a Quick Recap You’ll Want to Catch Up On
We presented a goldmine of insights on building lasting client relationships—and how those relationships translate into steady, low-stress income. The live Q&A brought up some great real-world examples (like what to do when clients don’t leave feedback! 💬), but even if you couldn’t join us live, the replay is full of useful takeaways. Here are three standouts:

🧭 Give Clients What They Want, Not What You Think They Want
New freelancers often overdeliver in the wrong direction. Nail the basics first—ask smart questions, deliver intermediate drafts, and let the client guide the final result.

🛡️ Offer a Friendly Safety Net
Add a satisfaction guarantee (like a 30-day free revision window) to ease client stress and boost your chances of a glowing review. ⭐

🔁 Don’t Just Ask for More Work—Frame It Smartly
Instead of “Do you have more work?”, try “Do you see anything coming up in the next 3–6 months we might work on together?” This subtle shift opens doors to repeat business.

🎥 If this was helpful, just imagine how much more you’ll get from the full replay (find it on your Barefoot Consultants platform) and next week’s live session!

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

See you next week!

🤖 This Week in the AI Lab: Instant Market Analysis = Freelance Gold

Winton gave us a live walkthrough of a powerful market analysis prompt—one that freelancers can use to generate a high-level industry report in under three minutes. 

He ran it from suggestions from the audience on the fast-growing fresh pet food industry, and in just a few clicks, ChatGPT delivered a data-backed market snapshot that would normally take hours (and even cost thousands) to produce.

We saw how AI scanned trusted sources like MarketWatch, Forbes, and Pet Insight, surfaced growth projections, spotlighted consumer trends, and even included a competitor breakdown and execution checklist. 

As Winton pointed out, this is the kind of service clients are actively posting jobs for every day—and most don’t know how to prompt AI like this.

Whether you're already a research pro or just AI-curious, this is one tool that can massively expand what you’re able to offer—and how fast you can deliver.

📌 Try the Prompt:

Perform a comprehensive market analysis of [insert market or product].

  1. Outline current and emerging trends, map the competitive landscape, and profile key consumer segments and behaviors.

  2. Back every insight with recent data and relevant statistics.

  3. Deliver clear, prioritized recommendations for exploiting underserved opportunities and accelerating growth.

Join the AI membership now and get instant access to the latest AI insights that help you work smarter, earn more, and future-proof your freelance career!💥

STATISTIC OF THE WEEK

Confidence—and Purpose—After 55

This week’s stat struck a chord:

9 in 10 people aged 55–65 believe they have transferable skills that can carry them into new roles or industries. And what’s even more interesting? Many are choosing second careers that are purpose-driven—not just income-driven. Think charity, youth programs, environmental work.

For anyone wondering what’s next after a long professional chapter, this data offers something rare and powerful: hope. It reminds us that our experience has value, not just in traditional jobs, but in meaningful work that aligns with our values and lifestyle.

Today, online platforms have made it easier than ever to apply your professional skills in flexible, part-time ways—often from anywhere in the world

Whether it’s lending your marketing know-how to a nonprofit or editing content for a cause you care about, there are ways to stay engaged, make an impact, and earn—without going back to a 9-to-5.

It’s not about starting over. It’s about building forward, with the skills you already have.

Want an answer to “What could I possibly do online?”

Heidi Craig, with over 20 years of experience in marketing, business development, and freelancing, can help you figure it out!

Her straightforward, impactful approach and diverse background make her the perfect guide to help you uncover your path.

CLICK HERE to book a complimentary 30-minute call to explore your options today!

🌎 Your Global Journey Starts Here ✈️
Join Us at an International Living Conference!

🌍Fast Track Costa Rica is on the horizon (May 23 - 26) followed by the biggest event of the year in
Portland, Oregon Aug 30–Sept 1

Four full days, and speakers covering destinations worldwide, the Ultimate Go Overseas Bootcamp 2025 event is perfect for those looking to explore new places and opportunities. 

If you're dreaming of a life abroad, these conferences are where the journey begins! ✈️

At each event, you'll gain insider strategies, expert advice, and valuable connections to help you navigate the path to international living with confidence.

 Exclusive Workshop with Winton! 
Discover how to create portable income and turn your dream of living abroad into a sustainable reality.

 See you there! ✈️ 🌏🚀

BOOK NOW!

📆 Mark your calendar and join us on the last Tuesday of EVERY month (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

👉Until then,
see you in our
Facebook Group! 😍😍😍😍