Is AI your assistant—or your replacement?

How the right AI tools can save you hours every week

Welcome Freelancer!

Next Tuesday, we'll show you how the right AI tools can save you hours every week without needing to be “techy,” and why staying human is still your biggest advantage in a world of automation.

Discover AI tools that boost your income (not threaten it)
Learn to let AI handle the grunt work
Stay in control—and ahead of the curve

👀 If you’ve been curious —but cautious— this one’s for you.

Register now for these weekly calls!

This week’s call recap: 🛠️ The Five Tools You Can’t Afford to Ignore

This week on Tuesday, Winton served up a practical, plain-English walkthrough of the five tools every digital nomad, freelancer, consultant, or coach must have in their toolbox to stay efficient, professional, and profitable—no matter where they’re working from.

He didn’t just list off tech names. He explained why these tools matter, how to avoid common mistakes (like time-zone mix-ups and lost meeting notes), and how to choose what to learn first without feeling overwhelmed.

“At one point, I had six calendars—two business, one personal, and three mystery extras.”
That was his wake-up call to simplify his setup—and a reminder to all of us that time management isn’t optional when you're building a portable career.

Here’s a taste of what he covered:

📅 Calendly – Gives a polished, pro-level first impression while solving the “what time zone are you in?” nightmare.
📝 Otter.ai – Transcribes your calls, organizes notes, and—with a little AI magic—spits out summaries and to-do lists from hours of conversation.
🎥 Zoom – Still the global gold standard for face-to-face connection, with bonuses like screen annotation and virtual backgrounds.
🤖 ChatGPT – Not optional anymore. Whether you’re writing emails, fixing grammar, or summarizing handwritten notes, it’s the shortcut every freelancer should use daily.
🔐 LastPass – For keeping your accounts secure without having to remember your dog’s birthday. 

Missed it? Watch the full replay and find out why now is the best time to get these tools working for you—before your business scales and you’re too busy playing catch-up.

🗓️ Mark your calendar for next Tuesday’s call—and this week let Calendly handle the scheduling.

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

See you next week!

QUESTION OF THE WEEK

“Did They Ghost Me... or What?”

If a client hasn’t checked in for a month, does that mean the job’s filled?

It’s the waiting game nobody likes. You sent a proposal, you felt good about it... and then? Crickets.

Winton kicked this off with a reminder: there’s no universal Upwork clock. He’s seen freelancers get hired two months after submitting. So no, silence doesn’t mean “rejected”—it might just mean “not yet.”

Heidi followed with a key shift in focus:

“You can’t control what they’re doing—maybe they posted the job and then left for a yoga retreat in Costa Rica.”🌴

Instead of wondering what’s happening behind the curtain, redirect that energy into what you can control: your next proposal.

✅ Is the job a great fit for your skills?
✅ Did you submit with clarity and confidence?
✅ Are you sending 3–5 proposals a week to build momentum?

“Every minute you spend wondering what happened is a minute you could spend writing your next proposal.”

Winton Churchill

Freelance success isn’t about reading minds—it’s about maintaining momentum. So let ‘em take their time. You’ve got more opportunities waiting.

Think You Don’t Have Anything to Offer Online?

Coach Heidi would beg to differ—and she’s got the track record to prove it

A UC Berkeley grad and globe-trotting freelancer with 20+ years in marketing, real estate, and business development, Heidi has a knack for spotting profitable skills you didn’t even realize were in your toolkit.

From training champion show horses to leading real estate marketing teams, she now helps 50+ professionals spot their most marketable skills and turn past experience into freelance traction—without burnout or starting over.

🎯 Curious what portable income could look like for you?
👉 Book a free 30-minute strategy session with Heidi and walk away with game-changing ideas, tailored to you. No pressure. No fluff. Just traction.

Portland sunset skyline with view of Mount Hood.

✈️Come to Portland with Us!

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

This isn’t just another conference. It’s a powerful launchpad designed to fast-track your overseas dreams with practical roadmaps, expert advice, and connections that matter. 

You’ll meet IL’s trusted country correspondents, real estate pros, legal and tax experts, expats who’ve already made the leap, and resource partners from around the world—all gathered in one place to help you make smart, informed moves abroad.

Whether you're craving beach life in Portugal, a jungle escape in Costa Rica, or a city adventure in Italy or Mexico, this is where the possibilities get real.

🎟 800+ attendees, 3 jam-packed days, and 1 unforgettable path to your future abroad.

Come hang out with us and get inspired!

AUGUST 30-SEPTEMBER 1, 2025

🎉 Highlights from our July After Party:
Ties, Tools & Travel Talk

If you’ve never stayed for the once-a-month after party… you’re missing half the magic.

This month’s session was packed with laughs, real talk, and some seriously sharp freelancing insights. The group swapped updates on what’s working (and what’s tricky) in their businesses right now, and Winton fielded a flurry of questions about AI tools—what he’s loving, what he’s watching, and where the tech is headed next for freelancers over 50.

🌍 We also took a mini world tour—chatting about what it’s like working remotely from different countries, adjusting to new cultures, and staying productive while living the expat dream.

And then came the After Party Quiz
Let’s just say it lived up to its reputation. We had our first-ever tie, but in true community spirit, the win was awarded to the person who had never won before, so Aileen F. walked away with the bragging rights!

Join us for our next AfterParty on the last Tuesday of August right after the Tuesday night call.

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