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The #1 Freelance Obstacle—and How to Beat It
Understand Your Job Success Score
Winton Churchill & Heidi Craig
April 18, 2025
Welcome Freelancer!
If you’re new to Upwork —or even if you’ve been around a while — your Job Success Score plays a bigger role in your progress than you might think.
Next Tuesday, we’re unpacking what this score actually is, why it matters from day one, and how it directly impacts how fast you land jobs.
We’ll also show you the common pitfalls that might impact your score and the simple steps you can take to raise it—and keep it high. Don’t miss this session if you want to start (or restart) your Upwork journey on the strongest possible footing.
👉 Register here free. If you registered since early February, you’re good to go! for the next 12 months—no need to update again! 💥
Algarve Coast, by Heidi Craig, from her recent trip to the International Living Conference in Portugal
If you missed the last Tuesday Night Call…
This week we walked through everything you need to know to set up your first (or next!) Project Catalog offering — an “off-the-shelf” service listing clients can buy instantly.
🛒 Upwork Project Catalogs: Your 24/7 Sales Machine
Here are key tips to get started:
✅ Start Simple: Begin with one project and build from there. You can have up to 40 total, but only 20 can be “live” at once.
✅ Use Tiered Pricing: Create Starter, Standard, and Advanced packages with meaningful price and scope differences — this allows clients to choose how deep they want to go with you.
✅ Images Matter: Eye-catching visuals attract clicks. Avoid logos, pixelated pics, or text-heavy graphics. Use a face, product image, or graphic that communicates your service clearly.
✅ Client-Ready = Confidence: Include FAQs, clear deliverables, and requirements so buyers know exactly what they’re getting.
💡 One tip? Treat your starter tier like a handshake—low price, low risk—and let your stellar delivery lead clients to your higher packages.
This system is a goldmine for freelancers who want to be found—not just searched for.
🎥 Catch the replay on your Barefoot Consultants platform to get help setting yours up!
Now, here’s the news from the Barefoot Consultants world….
See you next week!
Each week in Winton’s AI Lab, you get hands-on insights into using AI more effectively in your freelancing.
On our last Tuesday Night Webinar, Winton demonstrated how to get better results from AI tools by being more specific and how to shape AI-generated content by assigning a "role" — even if you're not an expert in the topic. He also showed us why giving AI flexibility with word count can lead to better, more natural writing.
Want to put this into action? Try telling AI to "write as an expert" in your field and see how it improves your results!
And don’t forget—each week’s AI Lab segment of the Tuesday Night call is packed with practical, easy-to-apply tips just like this.
And if you’re ready to really dig deeper into AI…
Join the membership now and get instant access to the latest AI insights that help you work smarter, earn more, and future-proof your freelance career!💥
Feeling Stuck Creating Your Project Catalog?
Struggling to find compelling project titles that stand out?
Spending hours crafting descriptions that clearly convey your value?
Unsure how to effectively price your offerings for maximum client attraction?
Feeling uncertain about how to design a professional graphic that captures attention?
Introducing:
Done-For-You Project Catalog Pro!
WHAT YOU’LL GET… | ✅ Expert-Crafted Project Titles: Instantly attract attention from your ideal clients. ✅ Detailed, Strategic Descriptions: Professionally showcase exactly why you’re the best choice. ✅ Optimized Pricing Tiers: Designed to convert more visitors into paying clients, while positioning you competitively. ✅ Professional Cover Graphics: Visually appealing designs aligned to enhance credibility and appeal. |
🔥 Special Pricing: $395 (Regularly $495)
Includes Valuable Bonuses:
⭐️ Upwork Profile Review & Optimization ($250 value)
⭐️ Exclusive Live Q&A Session on Winning Higher-Value Clients ($200 value)
⭐️ Personalized Proposal Feedback (Next 3 Proposals) ($150 value)
Limited Spots Available – Claim Your Package Now!
🌎 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! ✨ | BOOK NOW!May 23-26: End of August: |
See you there! ✈️ 🌏🚀
📆 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!
See you 👀 Tuesday, April 29th @ 8pmCDT
Challenge yourself, connect with other freelancers, and have a blast while picking up valuable freelancing insights!
👉Until then, |
