The Great Holiday Q+A - Unplugged

Greetings Portable Income Earner!

What would you ask if you had an open floor and direct access to people who’ve seen thousands of freelance profiles, portfolios, and career pivots actually work?

That’s what next week’s call is all about.

We’re hosting a pre-holiday, unplugged Ask-Us-Anything — a wide-open session where we truly cover the waterfront: profiles, portfolios, job strategy, positioning, and the real-world questions that don’t fit neatly into a slide deck.

Bring the questions you’ve been holding back:
 “This worked for someone else… but how do I make it work for me?”
 “What’s the smartest move I can make before the year ends?”

It’s live, interactive, and always a lot of fun (yes, virtual champagne included 🍾). 

If you want clarity, momentum, and expert eyes on your situation before the year wraps up, this is the call to be on.

On this week's Tuesday Night Call, we tackled a topic that’s showing up in more and more client conversations: navigating AI preferences—without awkwardness, fear, or missteps.

The big takeaway is that AI itself isn’t the issue; misaligned expectations are. Clients fall along a spectrum—from AI-enthusiastic, to cautious, to firmly AI-averse—and none of those positions are “wrong.” Problems only arise when preferences go unspoken.

We walked through a practical framework for understanding those client attitudes, how AI is actually being used behind the scenes (as an accelerator, assistant, restricted tool, or not at all), and why your experience, judgment, taste, and accountability remain the real value clients are paying for.

We also shared simple, non-threatening language you can use to surface AI preferences early—questions that build trust instead of raising red flags—and discussed when it’s appropriate to address AI at all (often, it isn’t). 

The goal isn’t to over-explain your tools, but to stay aligned, professional, and prepared.

If AI has ever felt like a potential landmine in client work, this session gives you a clear, grounded way to handle it—confidently and on your terms.

👀 Don’t miss next week’s call! — If this will be your first time attending, click here to REGISTER NOW

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

One Insight You’ll Use This Week (Save This)

Before we get to the rest of the news, there was one moment from Tuesday night’s call that’s worth pulling out and keeping close.

We spent time unpacking something many freelancers are quietly wrestling with right now: how to navigate a client’s AI preferences without creating friction, fear, or awkward conversations.

The key takeaway surprised a lot of people:

There is no “wrong” AI preference — only undisclosed ones.

Clients generally fall into one of three camps:

• AI-enthusiastic (speed, iteration, innovation)
  

• AI-cautious (efficiency plus human judgment)
  

• AI-averse (human-only, often driven by trust or compliance)
  

What matters isn’t which camp they’re in — it’s knowing where they stand early enough to align expectations and protect the relationship.

On the call, Winton and Heidi shared simple, non-threatening language you can use to surface preferences without sounding inexperienced or defensive — questions that actually increase trust instead of eroding it.

📌 Save this mindset:
Your value isn’t the tool.
Your value is your judgment, taste, experience, and accountability — AI simply accelerates what only you can do.

If this is coming up in your client work (or you feel like it’s about to), the replay and summary walk through the full framework and exact phrasing.

👉 Members can watch the replay or skim the session summary here

Never Lose a Training Moment Again

That insight above is a good example of something we hear all the time:

“I remember Winton covering this… but I can’t remember where.”
 “Did Heidi share language for that?”
 “There was a template for this — I know it.”

Which leads us to something Winton walked through in detail on Tuesday night…

The Freedom Vault (what it does for you)

The Freedom Vault was rebuilt for one simple reason:
your training shouldn’t vanish the moment the call ends.

Instead of digging through long recordings or scattered notes, the Vault gives you:

• Every Tuesday Night Call, recorded and organized

• Clear session summaries so you can find what you need fast

• All handouts, templates, and links saved together

• Searchable access across 40+ hours of training (and growing)

• Timestamps so you can jump straight to the part you need

In other words, when a question comes up — AI preferences, proposals, portfolios, client conversations — you don’t start over. You look it up.

This is especially helpful during busy weeks (or holidays), when you want the insight without re-watching an hour-long video.

👉 Take a look at the Freedom Vault here

It’s designed to work alongside you — not overwhelm you — and to make sure the best guidance you’ve already earned stays usable when it matters most.

Both workshops will open first to those on the waitlist, then to members, and finally to the general public — so if you’re thinking of joining, get your name in early before we hit capacity again!

✨ ✨ ✨ ✨ ✨ 

🌍 International Living Fast Track Events

Panama (March) • Rome (Europe Fast Track- April)

Thinking about living abroad… or just spending more time somewhere extraordinary?

The International Living Fast Track events are immersive, information-rich experiences where you meet people who are actively exploring life outside the U.S. — and get real, practical guidance on how it actually works.

• Panama (March): A stunning city, an incredible harbor, and one of the best first places to explore international living.
  

• Rome (Europe Fast Track): The first-ever event in Italy — and an excuse to arrive early, stay late, and experience Europe with purpose.

These events are known for their community, clarity, and (believe it or not) running exactly on time.

👉 Get the details about IL events before all the spots are gone.

This year, we’re doing something a little different — and even more fun.

Instead of our usual Tuesday Night Call plus a separate After Party, we’re rolling everything into one full, power-packed hour on December 30 — right in that sweet spot after the holidays and before the new year officially begins.

Expect a live, interactive Q&A and roundtable-style session where you can:

• Bring your real questions (portfolio, proposals, AI, clients, next steps)
  

• Share what worked for you this year — and what didn’t
  

• Get clarity on how to head into January feeling focused, not rushed

This is one of our most conversational calls of the month — less presentation, more you in the room with us.

And yes… there may be a quiz, there may be a prize, and there will definitely be good energy as we close out the year together.

📅 Join us live on December 30 — it’s the perfect way to wrap up the year and set yourself up for a strong start in January.