Perfect roadmap for the retirement failure, travel-loving freelancer!
If you are looking to break into freelancing without the guesswork, Barefoot Consultants is the place to get started. Their system for turning lifelong skills into freelance opportunities is brilliant, supported by excellent courseware and live weekly training.I joined this program because I realized I’m quite bad at staying retired, but I'm not interested in a full-time grind. Freelancing provides the perfect balance of professional engagement, income, and the freedom to explore the world.Working with Winton was the highlight of the program. He is a master of his craft and such an interesting character—his endless experience, humor, and patience made the entire process seamless. He showed me how to apply my skills in ways I never imagined possible, giving me the genuine confidence to pursue new opportunities.With the foundation now in place, I’m eager to fuel my professional growth through the video library and weekly presentations as I transition into becoming a high-earning freelancer.Highly recommended!
Rita Meskel
I joined Barefoot Consultants to learn…
I joined Barefoot Consultants to learn how to transition into freelancing, and the program has been practical and easy to follow. The focus on using existing skills made the process feel realistic and manageable.Winton is my consultant, and he's knowledgeable, supportive, and easy to work with. His guidance has helped me better understand how to position myself and take clear next steps.Overall, a positive experience and a great resource for professionals exploring freelancing, especially later in their careers.
Chris
Freelancing over 50+? This System Works - No Guesswork Required!
Navigating the world of freelancing as a 50+ professional can feel like wading through an overwhelming sea of advice, much of it contradictory or impractical. That’s why Barefoot Consultants stands out—it doesn’t just offer another generic “how to freelance” guide. Instead, it provides a finely tuned system that separates the noise from the truly actionable steps, helping professionals transition into freelancing with clarity, efficiency, and confidence. As someone who has spent years in the corporate world, I knew freelancing was a logical next step, but I was immediately confronted with a flood of conflicting advice. What platform should I use? How do I price my services? Do I need a niche? What’s the fastest way to build credibility? There are thousands of opinions online, but Barefoot Consultants’ approach is different—it eliminates the guesswork by providing a structured, proven process that has been refined over 16 years and used by thousands of professionals worldwide. I personally joined the VIP Program, and it has been one of the most valuable decisions I’ve made. Unlike the overwhelming DIY approach most freelancers attempt, the Barefoot system gives you a streamlined roadmap—one that is tailored to professionals who aren’t just dabbling in freelancing, but are serious about making it a sustainable, income-generating career. One of the most critical insights I’ve gained is understanding how the freelance landscape is evolving for those 50+. The fastest-growing job sector for this demographic is remote freelance work, yet most of the advice out there is geared toward younger professionals, side hustlers, or hobbyists. What Winton and his team have done is create a system that speaks directly to ex-corporate professionals who are ready to leverage their experience, position themselves powerfully, and build a real, thriving freelance business. Another thing I appreciate is how efficient the process is. There’s a lot to learn when transitioning into freelancing, but Barefoot Consultants helps you move forward as quickly as possible, with as much certainty as possible. Winton’s method isn’t about trial and error—it’s about cutting through the unnecessary complexity and showing you exactly what works, step by step. If you’re 50+ and looking to build a remote freelancing career, I highly recommend Barefoot Consultants. Whether you’re exploring options or ready to make a serious move, this system will save you time, frustration, and uncertainty. Instead of trying to figure everything out on your own, you get a clear path to success—one that has already worked for thousands of people just like you.
Dia North
When I came around Barefoot Consultants…
When I came around Barefoot Consultants I wasn’t sure what I was looking for, as I was semi-retired and “not done yet”. LOL I attended an event in Denver, which provided clarity and confirmed the professionalism I was looking for. I’ve come full circle and now have a plan of action to utilize my own skills and create another stream of income. Coming full circle I now embrace my vision in everything I do. Thank you, Winton Churchill for being a font of knowledge and an exemplary guide through the morass of information. Forever grateful in New Jersey.
June Kellogg
The active Boomer's #1 ally!
If you're a Boomer frustrated by technology while anxious to still offer your skills, knowledge and life experience to the world, then Winton Churchill and his colleagues will be your BFBF--"Best friends, Best find!" RARE in today's world, their patience is even more infinite than their store of knowledge. Barefoot Consultants keep their courses current and their faith in you constant as you climb the ladder of success. Cannot recommend highly enough..!
Andrea Zinga
A good way to learn AI
The AI Membership series is a fun and easy way to learn and use AI. The video courses led by Winton and Evan are entertaining and easy to understand. You are able to go through the videos at your own pace. Whatever the topic, the AI prompts used, are straight forward and easy to use. The prompts used in the video course are available to download when the video is available. Once a month there is a Zoom call for Q&A about the recently released videos. This is a good way to keep up to date with new technology.
Bruce
Barefoot Consultants helped me get my first freelance gig!
I joined the Barefoot Consultants' Portable Income Masteclass in order to learn how to become a Digital Nomad. The program focused on how to effectively use UpWork. The program was professional, informative and supportive. I am thrilled to share that using what I learned in the program, my first proposal was accepted! Sign up for Barefoot Consultants if you want the freedom of being a freelancer.
Virginia Head
Winton's Portable Income Master Class
Winton's Portable Income Master Class has been indispensable in helping me:*get laser-focused on my freelancing goals and objectives;*move quickly and effectively through the Upwork profile and portfolio processes (like using bullet points as I am here!);*learn how to pick up the initial freelancing jobs that will level up my Upwork status; and*immediately begin my career as a Portable Income Master to complement my new lifestyle now that the kids have graduated college and are doing their own thing.Thanks, Winton. Looking forward to sharing my successes with you and the Master Class.
Brian
Excellent guidance & insights
Barefoot Consultants offer an insightful and motivating program to introduce the world of online freelancing to newbies like myself. The program is well-structured, thoughtful, adapted to the over 50 crowd, with a warm and welcoming vibe. Winton and team really go the extra mile to make sure you feel supported, get your questions answered, and dispel any qualms you might have. They provide the tools and expertise newbies need to avoid the usual pitfalls and get off to a successful start. I’m so happy I signed up for the Masterclass— I now feel confident and motivated to embark on this new chapter in my career, knowing that Barefoot Consultants is there to guide me along the way and provide me with the knowledge and tools to succeed!
Jenny Kaser
Great experience with Winton and Barefoot Consultants
I had been following Barefoot Consultants for some time and entered the Jumpstart program, with Winton as my coach. I cannot say enough about how positive this experience has been. His focus was on thoroughly familiarizing me with the Upwork platform. In every session, he shared deep insights and tools for me to apply. He is a very considerate coach, highly professional and knowledgeable, generous with his time, very responsive to my needs, and a great teacher. Now I value him as a friend.
Kenneth Jones
Highly recommended!
I highly recommend Barefoot Consultants! If you are looking for additional income as a freelancer this is the company to work with.Winton Churchill and his coaches teach a process that makes learning how to earn income from freelancing really easy. They are extremely knowledgeable, professional, and wonderful to work with.They offer lots of support to their clients - on weekly calls on specific, timely topics with lots of time for questions and answers, in a Facebook group where clients can post questions that are quickly answered, and through programs that are top-notch when it comes to helping someone who is new to freelancing learn how to start making money almost immediately with a simple, step-by-step process and all the tips and tricks required to make freelancing successful and enjoyable.The team shows how easy it is to get started with freelancing and how anyone with any type of background can find work that will enable them to work from anywhere in the world when they wish to work. They show how doable it is to make money from freelancing to create a freedom lifestyle with skills that absolutely everyone has.
Connie
Winton and Barefoot Consultants help me…
Winton and Barefoot Consultants help me transition from a corporate job to freelancing. I had no clue how to really start. Winton's program and team gave me the knowledge and guidance to transition to full-time Freelancing!
James Bellew
Skipped the guesswork
The best part about Barefoot Consultants is that I didn’t have to figure out freelancing on my own. Many of the questions at the beginning of any new business such as ‘what do I sell?’, ‘whom do I sell it to?’, ‘how much to charge?’, and many more were already answered with the test of time and the testament of success. The simple proven winning formula was literally laid over the top of skills I already possess which were so kindly and carefully uncovered by my certified coach. Had I known that I would have such a competent guide to help me move through this time of transition from my previous careers, work and life experiences, into being my own boss, creating my own hours and literally showing me how I can work anywhere I can get an internet connection, I would have paid double and started 5 years sooner.
Heidi
Motivational and Informative
My year and a half association with Barefoot Consultants has been wonderful, informative and even fun. It has introduced me to a whole world of online possibilities that I was completely unaware of before I took the Online Freelancers workshop in 2021. I have enjoyed the workshop, the Tuesday webinars, the regular information to help build my confidence and knowledge about online freelancing, the very specific and caring help from my coach last year, and of course Winton's friendly and enthusiastic approach (and David's thorough question wrangling!). The team is obviously dedicated to helping people transition to the online freelance world. In addition to the information provided at workshops, they go to great lengths to host a weekly webinar, the freelance Fridays on Facebook, YouTube videos, and offer regular tips and articles to keep you motivated and informed. I've always felt the team members do this work, not just because it's a "job," but because they love passing on their expertise to others. Engaging in their activities feels very inclusive. They have a real "can do" approach, which is motivating and encouraging, especially to those of us who are unsure or hesitant about entering the online freelance market.
Marcia
The on line lectures presented by…Excellent guidance for starting on-line freelancing.
The on line lectures presented by Winton & his team are so informative: particularly in relation to setting up on line freelancing & also being aware of pitfalls for newcomers. They put a lot of effort into these sessions & they have been very helpful & are continuing to improve these presentations to help those about to start their new freelancing careers. Thank you so much.
M.J.
I liked the content
I liked the content. However, I had some medical issues that I had to deal with....since then I have sent a message to my coach, but have not heard from her.It is/was my understanding that I should still be able to complete the program. Or, is there at least a partial refund?Thanks,Evelyn Szprejda
TOPAZ
i am disabled and inquired some time…
i am disabled and inquired some time ago about a disability discount and any programs for people with disabilities .... no answer,,,
Eric
Provides helpful information for free…
Provides helpful information for free lancers and provides information on best practices to follow and information on pitfalls and what should ring alarm bells about the prospective client.From what I garher, one part is still not very fleshed out for the newbies on how their lifetime experience relates to a marketable skill set post retirement in a fast changing tech environment. Many with long years of experience do not possess the degrees or certificates rquired. For example, many people have worked as Project Managers over a long period of time with a company but never needed to acquire the PMP certification. Actually when they starting managing projects, even large ones, there was no PMP and certifications.
Ejaz
Awesome experience interacting with Winton and Coaches
Great company, great courses, great support. Winton is always ready to help and take extra time to explain
Doug
I have What are you talking about?!not used or requested your…
I have not used or requested your services.
Scott N
