Cracking the Client Connection Code

An Exclusive Buyer Interview

Winton Churchill & Heidi Craig
November 30, 2024

Welcome Freelancer!

One of the biggest fears people over 50 have as they start their portable income career is of their potential clients.

If you’re over 50 and stepping into the world of portable income, one of the biggest challenges can be your perception of clients. Many new freelancers imagine clients as mean, demanding, or unreasonable—and this mindset can hold you back from playing full out.

Here’s the truth: this fear stifles your growth!

You hesitate to bid with confidence.
You second-guess your ability to land projects worthy of your decades of experience.
You miss opportunities to showcase your talent and expertise.

It’s time to shift your perspective and unlock higher earnings!

Earn more cash when you shed the fear…

Join me this Tuesday night for an exclusive live event:

Cracking the Client Connection Code: An Insider Buyer Interview

Get rare, behind-the-scenes access as we interview a real Upwork client! You’ll discover:

How buyers craft job descriptions that attract top talent.
What they look for when evaluating freelancer profiles.
The key factors that make them choose YOU over the competition.

This is your chance to gain insider knowledge and eliminate the guesswork in working with clients.

You’ll walk away with the confidence to bid on better projects, secure higher rates, and deliver results with ease.

This session is a game-changer. Don’t miss it!

See you Tuesday night—your next level of freelance success starts here!

Don't miss this essential session to set yourself up for freelance success!
Register here free.

Now, here’s the news from the Barefoot Consultants world….

See you next week!

Winton

ARTICLE OF THE WEEK

Want to skip the tourist traps and immerse yourself in authentic culture while freelancing?

READ THE FULL ARTICLE

Thailand was just named Travel + Leisure’s 2025 Destination of the Year! Discover the hidden gems where locals love to go—perfect spots to soak in the real Thailand, find inspiration, and work with a backdrop of vibrant history and stunning landscapes.

Testing a place like this lets you experience the heartbeat of a community without committing your freelancing spirit to a one-and-done decision.

PRODUCTIVITY TOOL OF THE WEEK

If you’re on the internet working and you come across an article or website you want to come back to later, when you have more time, that’s the time to make you of the Evernote webclipper: a FREE plug-in for your browser.

Winton has been using Evernote for 10+ years and has an extensive library of articles and websites he’s clipped. This becomes a brilliant resource library and tool.

Check it out and streamline your time by saving some of these potential rabbit holes for later.

JOB OF THE WEEK

A brilliant starter job for nearly anyone, this week’s Job Search highlights choosing the type of client you want to work with.

Numbers 1-5 (in the “About the Client” section to the right of the job description) exemplify the positive attributes you’re looking for, from Payment Verified, to a 5-Star rating in almost 300 reviews. Top it off with a 90% hire rate and $50K spent, this seems like a client that knows how to work with new freelancers.

A safe bet for a good experience from which you should be able to emerge with a 5-Star rating and some pay under your belt. This is what you’re going after as a newbie on Upwork.

Points 6 & 7 are simply additional items of info to help you gauge if the job is right for you. For example, if you don’t live in the U.S.A, you’ll want to skip this particular job (7).

Information like this is what you get by joining us on the Tuesday Night Freelancer Call. There is always something more to learn about this freelancing process.

Be sure to sign up on the link in this week’s newsletter and we’ll see you there!

Thanks to Coach Heidi Craig for this week’s Portable Income Pointers…

Heidi is a Barefoot Consultants Certified Coaching Professional with over 20 years of expertise in marketing and business development, dedicated to helping freelancers achieve their goals with a straightforward and impactful approach. Get help & advice by reserving a time to talk.

30 min complementary consultation

Let an expert help you showcase your skills

Get your profile DONE FOR YOU.

Why struggle with the guesswork of creating your Upwork profile when you can have experts design a polished one, showcasing your skills perfectly?

Our “Done-For-You” service creates a professional, targeted profile that highlights your skills, attracts clients, and gets you up and running quickly—without the stress.

Let us be your guide to freelancing success, saving you time and pointing you toward growth from day one.

This is your BEST Holiday deal:

5 one-on-one sessions – Coach writes profile, interviews you + more
52 Tuesday Night Webinars (one year)
Bonus: The Beginner’s Guide to Research Program $247
Bonus: One hour with Winton (1-on-1) $250
Total List $ 1,292
Only $636
Savings $ (50%)

Get this
SPECIAL OFFER!

$1292 $636

Calling all Barefoot Consultants Freelancers!
Mark your calendar for our first
Freelancer Afterparty of 2025!

This is your chance to connect face-to-face with Winton, his team, and a community of like-minded freelancers who share your drive for building portable income and living life on your terms.

🎉 SEE YOU Jan 28, 2025! 🎉

Make Sure You’re Signed Up! Use this link to register for the After-Parties and receive reminders as we approach January’s event.

👍

In the meantime,
see you in our Facebook Group!