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- 7 Common Mistakes New Bidders Make!
7 Common Mistakes New Bidders Make!
Which mistakes might be costing YOU clients?

Welcome Freelancer!
Think your proposals are solid but you’re not landing jobs?
You won’t want to miss next week’s webinar when we dive into the 7 Common Mistakes New Bidders Make! 🎯 Find out if one (or more!) of these 7 mistakes is costing you clients.
This session will show you:
⭐️ How to shift your perspective and approach bidding like a pro
⭐️ The biggest pitfalls that stop new freelancers from winning work
⭐️ How to fix these mistakes instantly and start seeing results
We’ve got a brand new sign-up link — make sure you’re registered!
👉 Register here free.
The good news? You only have to do this once, and you’ll be registered for the next 12 months—no need to update again! 💥
📅 So join us Tuesday, March 11th, and set yourself up for more wins, better clients, and a freelance business that thrives.
Missed the call last Tuesday?
Catch up on the replay for the Top 3 Proposal Strategy Takeaways from "Insider Proposal Strategies That Win"
1️⃣ Customize Every Proposal, But Not From Scratch – The best freelancers don’t write proposals from the ground up every time. Instead, they use reusable templates that are 20-30% customized to match each job description. This ensures efficiency while still making every proposal feel tailored.
2️⃣ Position Yourself as a Problem-Solver, Not a Job Seeker – Instead of saying, “I have 10 years of experience,” frame it as, “My decade in X industry means I can help you achieve [client’s desired outcome].” Clients don’t care about your background unless it directly solves their problem.
3️⃣ Leverage the Buyer’s Own Language for Maximum Impact – Proposals that echo the exact phrasing of the job description create an instant sense of alignment. Smart freelancers identify key terms exactly from the job description and weave them in naturally, making the proposal more engaging and relevant.
💡 Want to see all the winning strategies in action? The replay is now available on the Barefoot Consultants platform. Just sign in and find them under Webinar Playbacks!
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 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!💥
FEATURE ARTICLE
Key Takeaways from Heidi’s and Winton's Comments on the Article of the Week:
AI Skills are in High Demand – An this scares the heck out of most freelancers over 50…The Upwork study highlighted that AI-related skills are rapidly growing, with a shift towards deep expertise over generalist roles… but there is Good News!
Freelancers Benefit the Most from AI – Winton emphasized that freelancers can leverage AI to enhance productivity and efficiency, which is why his AI program was launched over a year ago.
Human-Centric Skills Matter – Both Winton and Heidi pointed out that AI cannot replace human skills like communication, problem-solving, and relationship-building, making these more valuable than ever.
Experience Over Degrees – The article reinforced the idea that proven expertise and decades of experience are more valuable in freelancing than formal degrees.
AI is a Tool, Not a Threat – Heidi recalled that early fears about AI replacing jobs have shifted, as AI requires human input to be effective.
Freelancers Should Stay Informed – Winton encouraged members to stay updated with changes on platforms like Upwork, especially around features like proposal boosting.
If you want to stay ahead of the curve and position yourself for success, this is a must-read.
Click here to read more about what’s trending and where your skills could take you next.

QUESTION OF THE WEEK
🔥Here’s a great question, submitted by one of our Barefoot members:
Are clients obligated to open, read, or respond to boosted proposals on Upwork?
❌ Short answer:
No, clients do not have to open or reply to boosted proposals. Boosting only increases your visibility, but it doesn’t guarantee a response.
However, ✅ Upwork currently refunds the extra connects spent on boosting if your proposal isn’t opened—though this policy could change anytime.
💡 Key takeaway: Only boost proposals for jobs where you are a perfect fit—throwing extra connects at a weak proposal won’t help!
Want to see Upwork’s latest rules on proposal boosting?
🔗 Click the link we’ve provided for the most up-to-date details!
🌊 Lost at sea in the vast ocean of freelancing?⚓A 30-minute consultation with Coach Heidi Craig is like having a seasoned captain guide you through uncharted waters, helping you plot a course toward success. With over 20 years experience in marketing, business development, and a range of industries, Heidi will help you steer clear of common pitfalls and set sail toward a thriving freelance career. Ready to find your true north?🚢✨ |
🌎 Your Global Journey Starts Here ✈️
Join Us at an International Living Conference!
Whether you're dreaming of a sun-soaked escape, a fresh start abroad, or the freedom of a location-independent lifestyle, International Living’s upcoming conferences are your gateway to making it happen.
Explore & Learn in Top Destinations:And The Ultimate Go Overseas U.S Boot Camp in Portland, OregonAt 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!April: Late May: End of August: |
This isn’t just another conference — it’s an eye-opening, action-packed experience that could change your future.
The world is waiting. Are you ready? 🌏🚀
👀 NEW After-Party Link!
Freelance Feud: The Barefoot Edition ROUND 3
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!
You only have to register once for the After-Parties, and you’ll be registered for the next 12 months—no need to update again!
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
📆 Mark your calendar and join us on March 25 after the webinar
👉Until then, |