- Barefoot Consultants® Portable Income
- Posts
- Insider Proposal Strategies That WIN!
Insider Proposal Strategies That WIN!
The secrets you need to know now, to get the jobs you want.
Winton Churchill
February 28, 2025
Welcome Freelancer!
Feeling a bit sheepish today…
Special note… I love technology but… every so often, as it improves, adds features, and makes security stronger it presents annoying little speed bumps.
Today is one of those speed bump days…sheepish for sure…
Due to technical changes and improvements with Zoom…we have a new link for our Tuesday Night Call… and while you are welcome to participate free in the live calls, you must sign up at this new link to continue to receive the announcements and the link.
Small good news…you only have to do this once and your signup is good for a full year… 52 weekly live sessions in all
Please sign up here to continue your free weekly access to the live Tuesday night call:
Back to the fun stuff…
If you tuned into this week’s webinar, you now know what not to do in your proposals. So it’s time to learn the powerful strategies that actually get you hired!
Next Week’s Webinar: Insider Proposal Strategies That WIN! ✍️
📅 Mark your calendar for March 4th—because we’re diving deep into proposal techniques that no one else is teaching. These are insider secrets you won’t find in generic advice blogs or AI-generated templates.
Here’s what you’ll discover:
✅ How to craft proposals that instantly grab attention
✅ The hidden strategy top freelancers use to win projects
✅ A must-know approach that increases your hiring chances—fast!
This is next-level proposal mastery. Don't miss out on the competitive edge that will set you apart. See you there! 🔑
If you missed this week’s Tuesday Night Freelance Call, ✍️ 3 Quick Fixes for Winning Freelance Proposals, and have been struggling to get responses to your proposals, here are three key takeaways that you can apply right now:
✅ Ditch the "I'm New" Statement – Clients can already see your profile details. Highlight your expertise and problem-solving skills instead of calling attention to inexperience.
✅ Make It About Them, Not You – Avoid the "I" virus! Focus on how your skills directly benefit the client’s project, rather than just listing your achievements.
✅ End with Confidence, Not Desperation – Skip the "I hope to hear from you soon" sign-offs. Instead, use a strong call to action like, "Click the hire button, and I’ll get started right away."
👀 Watch the full replay now in the Webinar Playbacks section in your Barefoot Consultants learning modules. 🎯
Now, here’s the news from the Barefoot Consultants world….
See you next week!
FEATURE ARTICLE
Stay Ahead or Get Left Behind: Essential Strategies for Freelancers Over 50
-John Canada with Winton Churchill
The freelance market is changing fast, and experience alone isn’t enough to stay competitive. Without continuous learning and adaptation, even the most seasoned professionals risk being overlooked.
The good news? A few smart moves can keep you ahead of the game.
Discover how one freelancer landed higher-paying clients with a simple skill upgrade, why micro-credentials can give you an edge over younger competitors, and the biggest mistake that could be costing you opportunities.
Don’t let outdated strategies hold you back—read the full article now and future-proof your freelance career.
 | Looking for some help with your freelancing?John Canada, with 20+ years of experience in marketing, business development, and freelancing, can help you figure it out. |
TIP OF THE WEEK
This week’s tip comes from Simon Sinek, a renowned leadership expert and bestselling author known for his insights on business, motivation, and success.
His advice? Clients don’t hire you just for your skills—they hire you for your attitude.
Freelancers who show confidence, adaptability, and a problem-solving mindset get hired and rehired, while those who second-guess themselves or seem desperate lose out. And it all starts with your proposal. If you position yourself as a true professional offering a service—not pleading for work—you’ll instantly stand out.
JOB OF THE WEEK
Market Research with a High-Value Client
This week’s featured job is a starter opportunity with serious potential—a market research project posted by a top-tier Upwork client with nearly $100K spent and a stellar 4.98-star rating from hundreds of freelancers.
Winton broke down why this job is more than meets the eye. The cryptic number in the title? It’s just the agency’s way of organizing multiple jobs for different clients. More importantly, this buyer has a track record of ongoing projects, meaning if they like your work, there’s a strong chance for repeat business.
One key takeaway: Follow the instructions exactly. This client specifically asks for “I have an address in the United States” as the first line of your proposal—don’t bury it elsewhere! Freelancers who miss small details like this often lose out before their proposal even gets read!
DEAL OF THE WEEK🚀
Write Proposals That Win—Faster & Easier!
Struggling to craft proposals that stand out? Get expert coaching and 4 custom proposal templates for the price of 3!
PROPOSALS | 🔹 Save time—write winning proposals in minutes, not hours |
🚀Freelancers have used these templates for years with incredible success.
Stop second-guessing your proposals and start getting hired!
🎯Why struggle with every new proposal when you can have a proven template that saves time and wins contracts?
Don’t miss this deal — click now to grab your package!
🌎 Your Adventure Starts Here: Join us at an International Living Conference! ✈️
Imagine spending a few days immersed in a world of exciting possibilities—where you’ll meet like-minded adventurers, gain insider knowledge, and jump-start your journey to a more flexible, rewarding life abroad.
Whether you're eyeing sunny Portugal, vibrant Costa Rica, or the iconic U.S. gathering in Portland over Labor Day weekend, these events are more than conferences—they’re gateways to your next chapter.
And the icing on the cake? Winton’s exclusive workshop is your golden ticket to mastering portable income strategies that make the dream of global living a reality. Ask questions, get personalized advice, and soak up wisdom from an expert who’s been helping thousands for over 16 years.
Here’s what’s coming up:
📍 Fast Track Portugal & Europe (April) BOOK
If Europe is on your radar, it’s worth getting on the waitlist. With insights into five European countries, this was one of Winton’s favorite conferences last year for both learning and sheer enjoyment.
📍 Fast Track Costa Rica (May 23-26) BOOK
Dreaming of pura vida? This conference is your chance to explore one of the best expat destinations in the world, with expert guidance on everything from residency to real estate.
📍 International Living’s Biggest Conference of the Year – Portland, Oregon (Aug 30 – Sept 1)BOOK
With 800-1,000 attendees, this event covers the entire world of international living. If you want a comprehensive roadmap to a life abroad, this is where you’ll find it.
🌴 Make it FUN. Make it transformative. Make it happen. The world is calling—are you ready to answer? ✨
Don’t miss the most exciting February After-Party of 2025…in MARCH! 🎉
Join us on Tuesday, March 4th for an unforgettable After-Party experience—our most beloved monthly event! It’s your chance to grab the mic, connect directly with Winton Churchill, and dive into a live Q&A where no question is off-limits.
🔔 Mark your calendar and join us!
REGISTER NOW FOR THE EXCLUSIVE AFTERPARTY LINK
(new registration required for each afterparty)
Meet your fellow Freelancers in the |
