- Barefoot ConsultantsĀ® Portable Income
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- šÆ Stop Chasing. Start Choosing.
šÆ Stop Chasing. Start Choosing.
And make yourself the easiest "yes" for a client.

Welcome Freelancer!
Ever feel like youāre sifting through hundreds of jobs hoping something fits? Thatās like searching for your lost contact lens under a streetlight ā just because the lightās better there ā instead of where you actually dropped it.
Next Tuesday, weāre breaking down how to use smart keywords to flip the game:
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So the right jobs find you
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So your proposals pop with the exact phrases clients are scanning for
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And so you stop wasting time on work thatās not a true fit ā or pays peanuts.
Weāll also show you how to freshen up keywords if yours feel ācold,ā and keep your search dialed in to jobs that truly value what you do best.
š„ This isnāt fluff. Itās how you skip the wrong work, land the right projects faster, and make yourself the easiest āyesā a client will give all week.
š Join us live ā or risk spending time hunting under the wrong streetlight.

š The New Playbook for Portable Income
This week on our Tuesday call, we broke down what we call the Freedom Protocol ā a smarter way to diversify your freelance (or remote) work so it genuinely supports your independence.
Itās no longer just about writing proposals. Winton laid out five evolving paths you can tap into right now:
Traditional job bids:
Still a staple on Upwork ā writing proposals for posted gigs. But only part of the picture.Project packages:
Pre-set services in Upworkās Project Catalog (think: $2,000 PowerPoints or $300 market research snapshots). Easy for buyers, and you can sweeten with bonuses like a strategy call.Consultations:
Growing fast. Many companies happily pay for an hour of your insight ā whether itās FDA approval advice or just helping them avoid expensive mistakes.Freelance-to-employee:
Some clients start with a small contract, then invite you into stable, part-time (or even benefit-eligible) roles if itās a good fit.Remote corporate jobs:
From clinical coordinators to pharmacy roles, Winton highlighted openings paying $70Kā$160K+. Imagine doing that work while living somewhere far more affordable.
š ļø How to put it to work
Mix your offers. Donāt just chase bids ā add a consult or project package you can share beyond Upwork (in emails, LinkedIn, with old colleagues).
Use your lifetime of know-how. A 30-minute session might lead to a full contract⦠or simply pay well for your hard-earned perspective.
Think bigger than Upwork. Itās just one small planet. Your packages and consultations can pull clients from across the entire globe.
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Takeaway:
The more doors you open for people to work with you ā proposals, packages, consults ā the faster you build steady income and real freedom.
Itās all on the replay. Pour a coffee, press play, and plot your great escape.
Now hereās the news from the Barefoot Consultantsā world,
See you next week!
QUESTION OF THE WEEK
Hereās a good questionā¦
If you update your skills on Upwork, does it change the jobs they send you?
ā Short answer: Absolutely!
Updating your skills is one of the smartest things you can do to fine-tune the opportunities Upwork sends your way. Just remember thereās a short delayāUpworkās algorithm needs time to ālearnā what you want by watching what you look at, search for, and bid on.
š Pro tip:
Whenever you finish a projectāespecially if your client praises something you did well (like research, writing, editing, analysis)āmake sure that skill is listed on your profile. The more your profile reflects what you actually do (and do well), the better Upwork can match you with jobs youāll love.
š Bonus:
Logging in often (even just to browse) keeps you visible. Upworkās system favors freelancers who show up regularly, so if you want the best jobs in your feed, consistency matters.
JOB OF THE WEEK
š§ Big Pay, Remote Life
This week Winton highlighted a different flavor of portable income: full-time remote jobs that pay like traditional careers ā but let you live anywhere.
On sites like Indeed, he showed roles that never existed remotely before the pandemic, such as:
š„ Clinical Research Coordinators ($70Kā$160K), managing teams from home ā ideal for those with a healthcare or project background.
š Reimbursement Managers at Novartis ($160Kā$297K), handling approvals and systems.
š„ļø Remote Pharmacy & Financial Clearance Reps, around $50K, perfect if you want steady work from Costa Rica or Mexico.
š¢ Healthcare Program Managers, running onboarding or compliance without leaving your kitchen table.
Many looking at these jobs are in their 50s or 60s, still wanting a strong income to finish off retirement savings ā or just done with the office grind. Some find them āmindless,ā but if you want high pay with total location freedom, theyāre worth exploring.
š” Takeaway for you:
These options didnāt exist pre-pandemic. If youād like a big paycheck but want it under your own palm tree, knowing how to target and sell your experience is everything ā exactly what we help you master.
![]() | Canāt quite see the online-income angle in your story?Meet Coach Heidi āBerkeley 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, Heidiās done the career pivoting (and the passportāstamping) so you donāt have to guess. Ready to uncover your portable-income sweet spot? |
Letās meet at the biggest IL event of the year!
See you in Portland, Oregon, Aug 30āSept 1
With 800+ attendees, four full days, and speakers covering destinations worldwide, the Ultimate Go Overseas Bootcamp 2025 event is perfect for those looking to explore new places and opportunities.
If you're dreaming of a life abroad, these conferences are where the journey begins.
See you there! āļø
BOOK NOW! | Ultimate Go Overseas Bootcamp 2025 AUGUST 30-SEPTEMBER 1, 2025 |
š NEXT AFTER-PARTY: šJuly 29th at 8pm CDT (right after the Tuesday Night Call)
Whether you played last month or youāre 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!
Need the join link? š REGISTER HERE You only need to register once and you will automatically get the link for the rest of the yearāno need to update again!
āļø Until then, |