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- đ âWhat Could I (50+) Possibly Do Online?â
đ âWhat Could I (50+) Possibly Do Online?â
Next Tuesday, we take a fresh look at portable income.

Welcome Freelancer!
Still wondering which digital gigs actually fit your skills (and lifestyle)? Wintonâs cracking that code next week with a fresh, no-fluff walkthrough:
Brand-new opportunities most 50-plus freelancers overlook
Why landing work keeps getting easier (tech + AI are finally on your side)
A rapid-fire tour of the top categoriesâso you can spot the ones that match your background in minutes
Live Q&A, real examples, and a few surprises we canât cram onto one slide đ
Whether youâre curious, stuck, or ready to level-up, this is your shortcut to picking the right lane and running with it.
Donât miss this crucial call to get your freelancing plans in motion.
đ Register here free. If you registered since early February, youâre good to go! for the next 12 monthsâno need to update again! đĽ

Missed Tuesdayâs call? Hereâs a brief recap of âPortable Income â3 Fast Take-Awaysâď¸â
Think Bigger Than âJust Another Project.â
Once youâve got a few Upwork wins under your belt, youâre allowedâencouraged, evenâto branch out. Review listings far outside your original niche (teaching, tutoring, consulting, marketing, etc.) and look for roles that tap all those decades of experience youâve collected. The marketplace is global and the demand is bigger than you realize.Five Proven Paths to Portable Cashflow.
Winton broke down five models that work almost anywhere in the world:Expat packages (take your employee role overseasâhousing, flights, perks).
1099 âportable-teamâ gigs (keep your job, become an outside consultant, raise your rates).
Project management services (sell the way you organize, schedule and communicate).
Online courses (turn what you know into evergreen, passive income).
Advisory/consulting (charge for your brain, not your hours).
Each has its own pros/cons, but they all beat burnout-inducing piecework.
Map Your Skills, Monetize the Gaps.
Draw a two-column chart: Things Iâm good at vs. Ways those could become advisory or passive products. Spin up ChatGPT to help flesh out service ideas, headlines and even draft outlines for coursesâyour full-time, AI-powered brainstorm partner never gets tired.
Catch the Replay
Missed the finer points? The full session (with examples and template prompts) is waiting in the Barefoot Consultants member portal âperfect weekend coffee viewing.
Now, hereâs the news from the Barefoot Consultants worldâŚ.
See you next week!
QUESTION OF THE WEEK
Website first?? Blog first? Or⌠what are the standard industry tools to count on for setting up my freelancing business?
đ Our answer? Upwork Is Your Website
Skip the tech rabbit-hole. New freelancers waste weeks tinkering with WordPress, colors, and credit-card plugins. None of that earns a dime.
Let Upwork carry the load. Your profile is a ready-made websiteâwith built-in marketing, payment processing, and millions of clients already browsing.
Learn tools on the fly. Need Google Docs, Sheets, Zoom, or Slack? Grab a free YouTube mini-course and get back to paid work.
Affiliate plans? Greatâafter youâve built a list and income. For now, nail the freelancing basics and cash flow first.

JOB SEARCH TIP OF THE WEEK
âď¸ Job-Hunting Quick Wins
(courtesy of BC Member Judyâs âTea Insertâ gig)
Run this 6-Point Client Check before you pitch.
Look for all six of the following green lights in right-hand sidebar of the job:
â Payment Method â | Tells you the moneyâs ready to rollâno âIâll pay laterâ drama. |
⥠Star Rating ⼠4.3 | Seasoned freelancers have already test-driven this client. |
⢠Location | Handy for time-zone overlap & cultural cuesâbut never a deal-breaker. |
⣠Hire Rate Greater Than 50 % | Proves they actually choose and pay freelancers instead of window-shopping. |
⤠Total Spend | A healthy wallet means repeat work and smoother approvals. |
⼠Member-Since Date | 3 Months Minimum |
đĄUse the â15 % Ruleâ on your opening bids.
When youâre still racking up history, bid ~15â20 % below the jobâs average price. Youâll win more projects, earn 5-star feedback faster, and let Upworkâs algorithm boost your visibility. (Stars firstâpremium rates later!)/
đŻTry it this week:
Search for a project in a hobby niche you love (tea, gardening, horsesâwhatever makes you grin).
Apply the 6-Point Client Check, mirror their keywords in your proposal, and bid that sweet-spot 15 % under the average.
Then tell us how it goesâand remember, any eye-catching posting you find can become our next Interesting Job of the Week. Just email the job link (no screenshots needed) to [email protected].
![]() | Canât quite see the online-income angle in your story?Meet Coach Heidi âBerkeley grad, globetrotting freelancer, and 20-year marketing & biz-dev pro who can spot monetizable skills faster than her Jack Russell spots a squirrel. From training show horses to marketing real-estate teams, Heidiâs done the career pivoting (and the passportâstamping) so you donât have to guess. Ready to uncover your portable-income sweet spot? (Fair warning: you may finish the call with fresh confidence and an urge to book flights.) |
đ Headed to Portland? So Are We!
Letâs Meet at ILâs Ultimate Go Overseas Bootcamp!
If you've been dreaming about living abroad, stretching your dollars further, or just creating your own "Plan B," this is the event of the year.
International Living is hosting their Ultimate Go Overseas Bootcamp in Portland, Oregon, August 30âSeptember 1, 2025, and weâll be thereâWinton and his crew of certified Barefoot Consultants coaches ready to connect, brainstorm, and cheer you on.
⨠Come get inspired. Come get a plan. And most of allâcome say hi! Weâd love to see you in Portland!âď¸ đđ
BOOK NOW! | Ultimate Go Overseas Bootcamp 2025 AUGUST 30-SEPTEMBER 1, 2025 |
đ Why Our Monthly âAfter-Partyâ Is the One Zoom Youâll Actually Look Forward ToâŚ
Unfiltered Q&A time â Open mics mean you can pepper Winton, our coaching crew, and fellow freelancers with every question youâve been stock-piling (yes, even the âsillyâ ones).
Crowd-powered breakthroughs â Someone elseâs question often sparks your aha-moment. Itâs like getting a mastermind session⌠for free.
Freelance Feud + prizes â Quick-fire trivia based on last weekâs webcast keeps the learning fresh and the laughs rolling (plus Barefoot swag for the winners).
Mini-recap on steroids â Even if you missed the prior Tuesday session, youâll catch the condensed âneed-to-knowâ bits while we play.
Community & camaraderie â Rub virtual shoulders with people who âgetâ the portable-income journeyâand cheer each other on.
đď¸ When? The last Tuesday of every month (same Zoom link as the weekly call).
đď¸ Cost? A grand total of âshow up.â
đĄ Payoff? Answers, ideas, networkingâand a healthier dose of fun than most business calls deliver.
Pop it on your calendar now, bring your favorite beverage, and come swap stories, win goodies, and leave smarter than you joined. See you at the After-Party!
Not getting the join link? đ REGISTER HERE You only need to register once, to automatically get the link for the rest of the yearâno need to update again!
See you đ Tuesday, June 24 @ 8pm CDT
âď¸In the meantime, |