Fast Track Your Way to 5 Stars

Smart Proposals for Small Jobs

Welcome Freelancer!

Next week, we’re going to dive back into proposals—something we haven’t focused on in a while, but it’s a cornerstone of success for freelancers at every level.

We’ll be talking about Fast Track to 5 Stars: Smart Proposals for Small Jobs—and it’s especially timely as we welcome some new members from our Freedom Protocol program.

Over the last six weeks, I’ve been working closely with some of you on the topic of starter jobs—the kinds of gigs that get you moving, build confidence, and lead to 5-star reviews fast. 

Next Tuesday, I’ll share how we apply our 7-step proposal strategy to those jobs in a way that builds traction quicker than most freelancers ever manage.

We’ll also cover:

  • What to say when you’re new—and how to say it well

  • How to spot “small” jobs with big potential

  • Why these early wins matter more than you think

Register now for these weekly calls!

This week’s call recap: 🧠 AI is your assistant, not your replacement.

On this past Tuesday night’s webinar, I walked everyone through a powerful reminder: AI isn’t here to take your job—it’s here to give you back your time. 

I shared real-life examples from my own workflow showing how AI helps me write faster, respond more clearly, organize ideas, and summarize complex documents in seconds.

We covered how your experience, judgment, and human touch are irreplaceable, especially when using AI for things like article outlines, meeting notes, email replies, and proposal prep. 

One of my favorite analogies? AI is like the invention of word processing—you could go back to a typewriter, but why would you?

I even demo-ed how I summarize a long transcript in under a minute using pre-built prompts—something that used to take me nearly an hour. That’s the kind of shift we’re talking about.

We also touched on:

  • ✉️ How I use AI to quickly respond to long, confusing emails

  • 🧾 Drafting and summarizing contracts (not legal advice—but sure is helpful!)

  • 🛠️ Automating repetitive tasks (like typing your phone number wrong one too many times)

  • 🧭 Why “boring but plausible” AI content needs your wisdom to stay honest and useful

This session wasn’t about fear—it was about how to stay in charge of your work by pairing your hard-won experience with smart, modern tools.

⚡ What’s the takeaway?

If you’re over 50 and wondering where you fit in this fast-moving AI world, know this: your value has never been higher. AI can speed up the “busy work,” but it’s your insight, clarity, and decision-making that clients actually pay for.

🎬 Missed it?

This is one of those sessions that will absolutely change the way you work.
 👉 Watch the replay ….You’ll walk away with practical tools you can use today—and probably a few laughs, too.

🗓️ And don’t forget to mark your calendar for next Tuesday —This is one of those calls that could shift your momentum entirely.

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

See you next week!

QUESTION OF THE WEEK

🎥 Question of the Week: Do You Really Need a Green Screen?

Barefoot Consultant freelance member, Rae, asked a great question that’s on the minds of many freelancers: What’s really necessary to look professional on a Zoom call? 

A good ring light and mic are a great start—but do you also need a green screen?

Winton shared some real talk about what freelance clients expect these days and why your Zoom presence matters more than ever—especially when it comes to getting hired. 

Whether you’re meeting a client for the first time or following up after a win, showing up well-lit, clear, and confident sends a powerful message.

To help you decide what setup is right for you, Winton dropped two videos with different approaches:

▶️ Video #1: In Favor of Green Screens
 Learn how to control your background consistently—no matter the lighting, distractions, or location.

▶️ Video #2: No Green Screen, No Problem
Prefer a simpler setup? This one makes the case for natural, fixed backgrounds that are easy to maintain.

Whether you go high-tech or low-maintenance, the key is to look like someone worth hiring. Check out the links, try a setup that works for you, and remember: they want to see your smiling face.

JOB OF THE WEEK

🍸Job of the Week: Cocktail Expertise Meets Copy Editing?

This week’s special guest coach, Ruth Houser, joined us from stormy Florida with one of the more unusual job listings we've seen: “Cocktail Expert.” But don’t let the playful title fool you—this Upwork post wasn’t looking for someone to mix drinks.

Ruth walked us through the listing, which called for a technical editor with deep knowledge of cocktail terminology, garnishes, and glassware—plus experience in academic editing, copywriting, and content development. Definitely not your average bartender gig.

But the real lesson? Unlikely listings like these can tap into skills you didn’t know were marketable. That time you spent managing a bar in college? Turns out it might just land you a freelance job.

⚠️ One red flag: This particular client had a 2.9 rating across 20 reviews—a good reminder to vet opportunities carefully before applying.

Ruth’s pick was a perfect example of why we say: you’ve gained more experience than you think—and somewhere out there, someone is looking for it.

Meet Coach Ruth Houser

Ruth is a CPA with 20+ years of experience at companies like AT&T, PwC, Lockheed Martin and Xerox where she developed a strong reputation as a decisive leader, driving profitability and growth through strategic financial management, process improvement, and innovative problem-solving.

👉 Book a complimentary 30-minute call to explore your options with Ruth’s help today!
 

Downtown Portland with view of Mount Hood.

✈️ Just 3 Weeks Away:
Come to Portland with Us!

There are still spots available for Winton’s Workshop on Friday, August 29th where you can gain in-depth insights into how to utilize the knowledge you already have to create your portable income lifestyle.

From August 30 to September 1, we’ll be at International Living’s Ultimate Go Overseas Bootcamp 2025—their only U.S.-based event this year—and we’d love for you to join us!

This 3-day, high-impact event is packed with practical advice, expert guidance, and real connections to help fast-track your dream of living or working abroad.

Whether you’re curious about Portugal, Mexico, Costa Rica, or beyond—this is where the “someday” plan starts getting real.

🌍 800+ attendees
🧭 3 days of insider info
🤝 1 chance to connect in person

We’ll be there. Will you?
👉 August 30–September 1 | Portland, Oregon

🎉 Join us for August’s After-Party on the last Tuesday of the Month, directly following the Tuesday Night Call.

Whether you played last month or you’re 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!

Looking for 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!

⭐️ Until then,
join us in our
Facebook Group! 😍