Join Over 300 Premium Members

This Isn't Just A Subscription

Our membership programs help people 50+ build successful portable income careers. Choose from two tiers offering expert content, live training, and coaching.

Premium Membership Monthly

$19/month

For those ready to invest in their success, our Premium Membership offers enhanced resources and direct access to ongoing support and training.
  • Weekly Live Training

  • Access to Recorded Webinars

  • Monthly 1-on-1 Coaching Calls

  • Private Facebook Group

  • Special Discounts

  • Freelancer Resource Module

Growing Your Portable Income With AI (Annual Subscription)

$19.95/month

Are you ready to take your freelancing and consulting career to the next level? Our 2025 AI Membership Program is designed specifically for professionals aged 50+ who want to leverage cutting-edge AI tools to boost productivity, enhance creativity, and achieve more with less effort. We explain this stuff the way you learn best, without a lot of jargon and theory! Practical bite sized sessions bring you into the world of AI in ways you’ll love… practical, down to earth, and immediately effect. 52 Weekly Step-by-Step Training: Learn how to use AI tools effectively with clear, practical guidance with these recorded sessions. 12 Live Sessions: Get insights from experts and stay updated on the latest trends. Interactive Resources: Access templates, workflows, and checklists to save time and effort. Supportive Community: Join like-minded professionals who share your goals and challenges. Monthly Updates: Stay ahead with new tools, techniques, and strategies.
  • 52 Weekly Step-by-Step Training: Learn how to use AI tools effectively with clear, practical guidance with these recorded sessions. 12 Live Sessions: Get insights from experts and stay updated on the latest trends. Interactive Resources: Access templates, workflows, and checklists to save time and effort. Supportive Community: Join like-minded professionals who share your goals and challenges. Monthly Updates: Stay ahead with new tools, techniques, and strategies.

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Testimonials

Why Upgrade?

“At 69, I moved from Canada to Cuenca, Ecuador. Barefoot Consultants helped me supplement my pension by teaching English at the University of Cuenca. Now, I work part-time, contributing to Ecuador's tourism industry while enjoying a fulfilling retirement. I've found the perfect balance of purpose and relaxation in my adopted paradise. It's never too late to reinvent your life.”

Bill Dixon

69-year-old Expat English Teacher living his dream in Cuenca, Ecuador

“After attending Winton's freelance call, I applied for a translation job using his template. The client responded positively the next day, impressed by my pre-proposal's professionalism. This immediate result boosted my confidence and showed me the potential in freelancing. Thanks to Barefoot Consultants, I'm not just dreaming about freelancing—I'm doing it and enjoying the process!”

Linda Wilson

Emerging Freelance Translator

“Barefoot Consultants' 21-day program transformed my career. I immersed myself in their content and landed my first job on day 21. Now, 60 days in, I have two long-term commitments and just secured another. Winton's promises about freelancing benefits have proven true. I'm gaining confidence daily, seeing steady progress, and enjoying the journey. Barefoot Consultants didn't just teach me how to freelance—they showed me it really works.”

Patricia P

Flourishing Freelance Copywriter

“Initially skeptical about Upwork, I followed Winton's course during a hospital stay. I set up my profile and started bidding with customized proposals. Within 48 hours, I received two invitations to bid and a request for samples. Though I haven't landed a job yet, the quick progress is clear. Barefoot Consultants transformed my view on freelancing platforms, turning my hesitation into hope and opening new possibilities.”

Steve M

Aspiring Freelancer

“Barefoot Consultants' program transformed my life. I discovered transcription as my niche and, after initial setbacks, landed three jobs within 36 hours. Two months later, I'm living my dream in South America. Writing from Peru, I can say: This is paradise! The program provided a clear path to freelancing success. From zero to living my dream in a short time - that's the power of this program!”

Thora Rasmussen

Freelance Transcriptionist living her South American dream

“After a year of inactivity, Barefoot Consultants revitalized my freelancing. Applying Winton's advice, I landed my first project after just 11 proposals. The course's value was clear - I recouped nearly half its cost with that first job. Now, I'm not just dreaming of location-independent income; I'm building it. Thanks to Winton, my dormant profile has become a thriving freelance business, supporting my goal of part-time living abroad.”

Idara

Emerging Global Freelancer

“Following Barefoot Consultants' advice, I landed my first Upwork job on my first bid! The key was bringing enthusiasm to each proposal. After that, invitations started rolling in. My advice: keep bidding and stay positive. Incredibly, I'm swamped with work before even finishing the course. Barefoot Consultants has truly unleashed my freelancing potential.”

Stephanie

Thriving Freelance Writer

“Years ago in Belize, I met a freelancer living my dream life—working from a laptop in flip-flops. After early retirement and divorce, I yearned for that freedom but didn't know where to start. Then I found Barefoot Consultants. Their program opened my eyes to endless possibilities, even for an 'odd-duck' like me with diverse skills. By the fifth lesson, I was no longer just dreaming—I was confidently planning my new freelance career.”

Cathy M.

Aspiring Digital Nomad

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