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The Secret to Freelance Stability
Cultivate client loyalty for steady cash flow
Winton Churchill & Heidi Craig
May 10, 2025
Welcome Freelancer!
✨Coming Up Tuesday: The Secret to Freelance Stability…
Tired of starting from scratch with every client? Next week, Winton reveals the proven strategies behind cultivating client loyalty and creating a steady freelance cash flow — the kind that keeps your calendar full and stress levels low.
You’ll learn:
✅ How to become the kind of freelancer clients want to rehire
✅ What truly satisfies clients (spoiler: it’s not just doing good work)
✅ How to turn short gigs into long-term income streams
This one’s about working smarter — not harder. Join us and start building the kind of client relationships that pay off again and again.
👉 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 What You Need to Know:
This week, we unpacked how to launch your coaching services on Upwork — even if you’ve never called yourself a coach. With over 3,400 coaching jobs currently open, the opportunity is massive, especially for those 50+ with real-world experience.
Top Takeaways:
📌 Create a client-facing profile: Focus less on “I did this” and more on how your experience benefits them.
🎯 Target the right clients: Use filters to find high-value, age-appropriate coaching gigs — from executive to wellness.
🧠 Highlight your wisdom: You don’t need certifications if you have a track record of results.
👉 Coaching is flexible, meaningful work that pays well and plays to your strengths.
📼 Catch the replay on your Barefoot Consultants platform or join us next Tuesday — you never know what doors Winton will open next!
Now, here’s the news from the Barefoot Consultants world….
See you next week!
Winton’s AI Travel Hack You’ll Want to Steal
On the call, Winton walked us through a live demo using AI to prep for an upcoming work-travel trip to Costa Rica—and the takeaway was both practical and eye-opening.
He showed how simply changing the way you ask a question can lead to a dramatically different (and often better) result. When he asked ChatGPT for “10 tips” for balancing freelance work and vacation, the AI delivered a solid, structured list.
But when he rephrased it to “What do you suggest?”, the results went deeper—offering more nuanced and personalized insights, from preloading proposal templates and cloud docs to optimizing your lodging for fiber-optic speeds.
Heidi chimed in with her own win from Portugal—replacing unreliable hotel Wi-Fi with a SIM card bought at the airport, which gave her blazing fast service for only 35 euros and made early morning work sessions a breeze.
Download the AI-generated document Winton shared by clicking on the link below. It’s yours to use as inspiration or you can even repurpose the prompt for your own travels. The big lesson? Try letting AI “run free” with a question instead of boxing it in with a numbered list—it might just surprise you with smarter suggestions
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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!💥
FEATURE ARTICLE
🧠 Why Coaching Matters More Than Ever — Especially Across Generations
On this week’s call, Heidi shared a Harvard Business Review article that’s a must-read if you're offering coaching or mentorship services as a freelancer.
It highlighted how today’s digital workforce is full of fast, capable younger professionals — but what many lack is perspective.
✨That’s where you come in…
✅ Wisdom = Metabolized Experience
Unlike technical knowledge, real-world insight can’t be Googled or replicated by AI.
👥 Intergenerational Teams Perform Better
Younger workers bring speed. Older professionals bring foresight, calm, and pattern recognition.
🌱 Mentorship Builds Cultures of Growth
A coach’s perspective helps younger professionals stay engaged, level up, and see the big picture.
This is your reminder that coaching isn’t just a gig — it’s a legacy. If you’re over 50, your experience might be your greatest freelance asset.
🔗 Check the replay for the discussion—and be sure to read the full article Why “Wisdom Work” is the new “Knowledge Work”
 | 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! |
🌼 Spring into Freelance Success with Our Done-For-You Profile Package! 🌼
Ready to skip the overwhelm and get straight to earning? Our Ultimate Done-For-You Upwork Profile Package is your shortcut to a polished, professional freelance presence—without the guesswork.
👉 WATCH this video clip that explains the entire program:
🌼WHATYOU GET |
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🌟 Spring Deal Bonuses:
1-Year Access to Tuesday Night Webinars (52 sessions!)
Exclusive AI Membership Program
1-on-1 Session with Winton Churchill ($400 value!)
💰 All for just $695 (Regularly $1,335 — Save 49%)
If you’re serious about launching (or relaunching) your freelance career with impact, this is your moment!
🌎 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 from August 30–September 1.
With 800-1,000 attendees, 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! ✨ See you there! ✈️ 🌏🚀 | BOOK NOW!May 23-26: End of August: |
📆 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, |
