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Writing winning proposals with AI
Using AI tools smartly (and ethically!)

Hello Freelancers! 🌍✈️
While the Barefoot Consultants team was flying across the Atlantic to the International Living Conference in Portugal this week, we didn’t leave you empty-handed!
In place of our usual live Tuesday Night Call, we shared a brand-new recorded session featuring Winton and Certified Coach Bruce on one of the hottest topics in freelancing right now: writing winning proposals with AI 🤖📝.
This session was packed with insights on how to use AI tools smartly (and ethically!) to improve your proposals, stand out to clients, and save time—without losing your personal voice.
Below, we’ve recapped the key takeaways, how you can apply them to your own freelancing work, and where to go if you want more powerful tools like this in your business toolkit. Let’s dive in! 👇
But first, a little about Coach Bruce Tamanaha… After a 20+ year career in healthcare IT, Bruce is all about editing and beta reading these days.
He’s also helping others with writing and AI projects. He’s skilled with ChatGPT, finding ways to make writing smarter and easier.
Bruce has reviewed plenty of books and worked with great authors. He knows how to keep feedback clear, kind and helpful.
He’s a down-to-earth guy who loves making projects better and more successful for his clients….and now, on to the hot tips!….
See you next week!
By the way, if you have been missing the Tuesday Night Calls…
👉 Register here free. If you registered after early February, you’re good to go for the next 12 months—no need to update again! 💥
💡 INSIGHT:
What AI Can — and Can’t — Do for Your Proposals
AI won’t write you the perfect Upwork proposal with one click (sorry, not yet!). But it can absolutely do 80–90% of the heavy lifting—if you guide it right.
That means less staring at a blank screen and more proposals going out the door.
Winton and Bruce demonstrated how ChatGPT can crank out a rough draft, freeing you up to focus on what really matters: making it personal, persuasive, and client-focused.
“ChatGPT writes informative text. It’s your job to turn that into persuasive copy,” Winton explained…
🛠️ HOW TO USE THE INSIGHT:
Proposal Tips You Can Apply Today
Ready to upgrade your proposals with AI? Here are 3 instant takeaways from the session:
✅ Stop Saying “I” So Much: Turn “I have 20 years of experience” into “You benefit from 20+ years of experience.” Make it about the client.
✅ Cut the Fluff: Drop ChatGPT’s generic openers like “Hello, my name is…” and the polite-but-pointless “Best regards.” Replace with a warm, professional greeting and a clear call to action.
✅ Add Emotion: A single sentence like “I love helping construction clients keep their customers informed” (with an exclamation mark!) can grab attention and build connection fast.
🚀 Want Help Doing This Step-by-Step?
This powerful walkthrough is just one of the deep-dive classes inside our AI Membership, where you’ll learn how to use ChatGPT to:
✨ Draft winning proposals faster
✨ Polish your profile and portfolio
✨ Save time while sounding like the pro you are
📌 Want to see exactly how Bruce rewrote a “blah” AI proposal into one that wins jobs? ➡️ Join the AI Membership NOW and get instant access |
More sessions like this drop monthly—so you can keep sharpening your edge with real-world tools and real-time support.
🌎 Your Global Journey Starts Here ✈️
Join Us at an International Living Conference!
Fast Track Costa Rica is on the horizon, followed by the biggest event of the year in Portland, Oregon from August 30–September 1. With 800-1,000 attendees, four full days, and speakers covering destinations worldwide, it’s the ultimate event for those looking to explore new places and opportunities.
If you're dreaming of a life abroad, these conferences are where the journey begins. Just two left for the year! ✈️🌎
Meet us in May in Costa Rica!Or join us at The Ultimate Go Overseas U.S Boot Camp in Portland, Oregon in late Auguest At each event, you'll gain insider strategies, expert advice, and valuable connections to help you navigate the path to international living with confidence. | BOOK NOW!Late May: End of August: |
✨ Bonus: Winton’s Live Workshop
Dive deeper into the field-tested strategies of how to create reliable portable income that travels wherever you do 🌎
Whether you're dreaming of a laid-back beach life or your next big global move—these events are your launchpad.
Can’t wait to see you there. 💼🍷🌅
Next After-Party 🤹♂️Tuesday, April 29th
@ 8pm EDT
📆 Mark your calendar and join us on the last Tuesday of EVERY month (right after the Tuesday Night Call)!
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
👉 REGISTER HERE for the CURRENT After-Party Link for 2025! (as of February - no need to register twice)
👉Until then, |