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- Your Year-End Boost: The 7 Strategies That Set You Up to Win
Your Year-End Boost: The 7 Strategies That Set You Up to Win
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Greetings Portable Income Earner!
We wrapped up a powerhouse session this week — and before we get into your recap, let’s talk about next Tuesday, because it’s one you’ll absolutely want on your calendar.
⭐ Next Week: Experience Into Evidence — The 3 Portfolio Upgrades Clients Notice
If you’ve ever wondered “What do clients actually look for in a portfolio?” this session is your answer.
We’ll be diving into:
How to turn past experience into clear, relevant proof of skill
What kind of “transformative moments” from your work history clients will respond to
Simple ways to show 3rd-party evidence (ratings, metrics, outcomes, credibility markers)
Fresh examples pulled from current projects
This is one of the most confidence-building sessions we teach — especially for those who have decades of experience but haven’t yet translated it into portable-income language.
If you want your portfolio to work harder for you in 2026, you don’t want to miss this.
👀 Don’t miss next week’s call! — If this will be your first time attending, REGISTER NOW

This week’s call was all about “7 Loose Ends to Tie Up Before 2026”—simple moves that let you finish the year with intention and start January feeling clear instead of scattered.
We walked through checking in with your current clients so you know what’s wrapping, rolling over, or ready to expand, then auditing what you actually delivered this year so you can decide which services to double down on (and which to quietly retire).
From there, we talked about refreshing your proof and categories so your profile, samples, and titles actually match the kind of work you want next, and putting a light plan under Q1—a short list of people to contact, projects to propose, and a quick cleanup of your admin, finances, and digital files.
We closed with a reminder to protect the asset: keep your skills sharp, your relationships warm, and your security settings (passwords, backups, logins) current so your portable income engine is ready to roll in 2026.
Now here’s the news from the Barefoot Consultants’ world,
A One-Minute Pulse Check for Your Portable Income Goals
Before we all slide into full holiday mode, we put together a quick Year-End Readiness Check-In — a simple 5-question survey designed to help you get clear on what to prioritize before we flip the calendar.
Think of it as a tiny pit stop between now and January that can save you hours later.
If you’ve been thinking…
“I should really get organized for Q1…”
OR
“I don’t know yet what January even looks like…”
then this little check-in will give you instant direction.
1. How clear are you about your January client workload and priorities?
I’m fully booked and organized
I have some clarity, but need to confirm things
I have no idea what’s coming yet
2. Which loose end feels MOST important for you to tackle?
Updating my portfolio with this year’s work
Refreshing my categories/overview
Clarifying my client commitments
Cleaning up admin & finances
Planning Q1
3. What do you want MORE of in 2026? (Choose all that apply)
Better-paying clients
Easier, more enjoyable work
Repeat clients
Clearer systems + less stress
More predictable income
4. What’s your biggest obstacle right now?
Not finding enough good-fit jobs
Still figuring out my category/skills
Client communication
Time/organization
Confidence in my next steps
🎉 Congratulations for taking the Year-End Readiness Survey!
Whether your answers felt like “I’ve got this,” or “Oof… time to tune a few things up,” here’s what we want you to know:
⭐ You already have strengths working in your favor.
By simply showing up, answering honestly, and taking stock of where you are, you’re doing what most freelancers never do — you’re checking your bearings before the new year starts.
That alone puts you ahead.
From where we sit, people who take this survey typically discover they’re already strong in things like:
Knowing the kind of work that feels right
Being willing to learn a system instead of winging it
Wanting clarity and consistency going into January
Recognizing the value of small steps that build momentum
These are the traits that create traction on Upwork.
🔧 And if a few answers made you think, “Yep… that’s where I need support”?
Good. That’s what this little checkpoint is for.
To make January feel dramatically easier, think:
Cleaning up or adding portfolio items
Refreshing your profile categories
Rebuilding your proposal rhythm
Clarifying the kinds of clients you want
Tiny hinges swing big doors.
🔧 Your Next Step: Set Yourself Up to Win in 2026
This week’s call made something crystal clear:
Most freelancers don’t need a massive overhaul — they need a few smart, well-timed tune-ups before the calendar flips.
These seven strategies are the same ones we walked through live, and they’re designed to:
Clear out the “mental clutter” that slows proposals
Help you tighten up your profile, searches, and systems
Reset your Upwork rhythm so January feels light, not overwhelming
Bring back the sense of control and clarity that makes freelancing enjoyable
Put you in the small percentage of people who start the year organized instead of reactive
They’re simple. They’re doable. And they deliver.
If any question in the survey gave you that “Yep… I should probably fix that” moment, this guide will walk you through exactly where to begin.
👉 Download your guide: Top 7 Year-End Strategies That Deliver

🌟 Coming Soon: The Portable Income Kickoff Accelerator (PIKA)
— Waitlist Now Open!
If you’ve been waiting for the right moment to get serious traction on Upwork, this is it.
Winton and Coach John Canada are officially gearing up for the third round of the Portable Income Kickoff Accelerator — a live, guided, small-group workshop designed to help you land your first two paid jobs and earn that all-important Job Success Score.
What makes PIKA different?
This isn’t self-study. You get Winton and John live each week — plus personal feedback between sessions.
You’re not doing this alone. Past participants say the community support was just as valuable as the training.
It works. Both previous cohorts had strong wins, momentum, and real confidence shifts.
Zero-pressure guarantee. If the six weeks end and you don’t yet have your Job Success Score, the support doesn’t stop. Winton and John keep working with you until you do.
If 2026 is the year you want portable income to move from “someday” to “actually happening,” this is the fastest, clearest path.
👉 Save Your Spot — Join the PIKA Waitlist
(limited seats, always fills quickly)
Think you’re “not techy enough” or “starting too late”?My favorite thing in the world is proving you wrong — gently, cheerfully, and with a plan that actually fits your life.I help 50+ professionals uncover the skills they didn’t even realize they had and turn them into portable income… without burnout, overwhelm, or hustle culture nonsense.👉 Book a free 30-minute session — bring your background, and I’ll show you what’s marketable before we even hang up. |
Both the below workshops will open first to the waitlist, then to members, and finally to the general public — so if you’re thinking of joining, get your name in early before they reach capacity!
💪 50+ Energy & Focus Workshop (with Dr. Rao)

Reignite your energy, focus, and productivity — built for freelancers over 50 who want to work smarter (and feel sharper). |
🚀 Portable Income Kickoff Accelerator
Begins January 21st — the signature workshop that helps you jumpstart your Upwork success with the proven Barefoot framework. |
✨ ✨ ✨ ✨ ✨
Join us in person this spring at Fast Track Panama (March 20) or the Rome Conference (April 10) with International Living.
Fast Track Panama 📍 Panama City, Panama | Fast Track Europe 📍Sheraton Rome, Rome, Italy 🎤 Winton’s Workshop: Friday, April 10 |

Because of the holiday season, this month's After Party will be combined with the Tuesday Night Call on December 30th…
This will be a live Q&A and roundtable-style session, more interactive than usual, with plenty of opportunity to ask your questions and share what’s working for you. And yes, rumor has it there may even be a little quiz — and maybe even a prize — to keep things fun.
🎯Join us in the Facebook Group! |






