LogoBarefoot Consultants® Portable Income
Authors
Login
Subscribe
Winton Churchill
Winton Churchill

Winton Churchill, CEO of Churchill Method, Inc., is renowned for his creation of the Barefoot Consultants courses, training products, workshops, seminars, and masterclasses aimed at enabling individuals over 50 to develop a portable income. His efforts have reached over 71,000 participants, leveraging his extensive 30+ year career in sales, marketing, product marketing, and business development across prominent technology companies like Apple, Sun Microsystems, and Oracle. At Apple, he was instrumental in the company's pivot to business computing in the early 80s. His roles at Sun and Oracle involved managing key business areas in aerospace projects at the national level, contributing significantly to early high performance computing and the internet's infrastructure. Winton's insights on technology have been featured in major publications, and he is an advocate for the value the 50+ demographic brings to various sectors, emphasizing skills, knowledge, wisdom, and resilience. He is the author of three books, with "The New Retirement" being his latest, focused on empowering post-career life through income, balanced lifestyle, and a sense of satisfaction derived from pre-existing skills and traits. Winton's diverse career also includes pioneering contributions to computer-based training programs and a rich history in photography (his first freelance job), encapsulating a multi-faceted approach to post-career fulfillment and societal contribution.

Your Best Selling Point Might Be Hiding in Plain Sight

Oct 30, 2026

•

4 min read

Your Best Selling Point Might Be Hiding in Plain Sight

Discover the connection between what you know and what a particular client needs.

Winton Churchill
Heidi Craig
Winton Churchill, +1
You Don't Have to Ride the Bad Horses

Oct 23, 2026

•

5 min read

You Don't Have to Ride the Bad Horses

One of the best things about working for yourself is deciding who deserves to work with you.

Winton Churchill
Heidi Craig
Winton Churchill, +1
The Consulting You're Looking For May Be Hiding in Plain Sight

Oct 16, 2026

•

4 min read

The Consulting You're Looking For May Be Hiding in Plain Sight

Sometimes the opportunity is there. You're just searching for it by the wrong name.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Trends

Exactly 36 Years Ago Today, The Wall Street Journal Asked Me About Email

Oct 12, 2026

•

7 min read

Exactly 36 Years Ago Today, The Wall Street Journal Asked Me About Email

And on that day fewer than 1% of Americans were online.

Winton Churchill
Winton Churchill

Motivation

Put a Stake in the Ground

Oct 12, 2026

•

5 min read

Put a Stake in the Ground

The decisions that change our lives usually begin when we stop waiting for the perfect time and commit to moving forward.

Winton Churchill
Winton Churchill
The Work You Stopped Noticing

Oct 11, 2026

•

4 min read

The Work You Stopped Noticing

After 20+ years of experience, the things that feel ordinary to you may be the very things someone else needs—and will pay for.

Winton Churchill
Heidi Craig
Winton Churchill, +1

strategy

+1

Quit Looking in the Low-Paying Jobs Section

Sep 11, 2026

•

4 min read

Quit Looking in the Low-Paying Jobs Section

If all you see are $25 and $50 jobs, the problem may not be the market. It may be where you're looking.

Winton Churchill
Heidi Craig
Winton Churchill, +1
Stop Asking, “Who Would Hire Someone Like Me?”

Sep 4, 2026

•

4 min read

Stop Asking, “Who Would Hire Someone Like Me?”

There’s a much better question—and it can completely change how you think about earning portable income.

Winton Churchill
Heidi Craig
Winton Churchill, +1
My Boss Had No Idea What I Did

Aug 28, 2026

•

3 min read

My Boss Had No Idea What I Did

Sometimes the most valuable thing you know how to do never appeared in your job description.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

+1

What Do You Want an Ordinary Tuesday to Look Like?

Aug 21, 2026

•

4 min read

What Do You Want an Ordinary Tuesday to Look Like?

Before you decide how much you want to earn, decide what you want your life to look like.

Winton Churchill
Heidi Craig
Winton Churchill, +1

mindset

+1

Your Next Chapter May Be a Chip Shot, Not a Reinvention

Aug 17, 2026

•

4 min read

Your Next Chapter May Be a Chip Shot, Not a Reinvention

How to turn the skills and experience you already have into practical portable-income opportunities—without starting over.

Winton Churchill
Winton Churchill
Same Expertise. Completely Different Impression.

Aug 14, 2026

•

4 min read

Same Expertise. Completely Different Impression.

Why the way you package your work can be almost as important as the work itself.

Winton Churchill
Heidi Craig
Winton Churchill, +1
I Couldn't Wait Until Friday to Share This

Aug 9, 2026

•

5 min read

I Couldn't Wait Until Friday to Share This

What Rick Beato, Billy Joel and Linda Ronstadt reminded me about life after 50.

Winton Churchill
Winton Churchill
Tell Your Story So Your Clients Listen

Aug 7, 2026

•

4 min read

Tell Your Story So Your Clients Listen

One small story can reveal more expertise than a 40-year résumé.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Your Experience Is Already There. Now Make It Visible.

Jul 31, 2026

•

3 min read

Your Experience Is Already There. Now Make It Visible.

Clients cannot hire what they cannot see. Here’s how to turn decades of experience into credible proof.

Winton Churchill
Heidi Craig
Winton Churchill, +1
A New Beginning: Join Us for This Free Freedom Protocol Orientation

Jul 28, 2026

•

1 min read

A New Beginning: Join Us for This Free Freedom Protocol Orientation

Join Winton and Heidi live on August 6—and discover how your experience could become portable income.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Stop Searching Like You Need The Work

Jul 24, 2026

•

4 min read

Stop Searching Like You Need The Work

A calmer system for finding better-fit Upwork jobs before you spend time evaluating or proposing.

Winton Churchill
Heidi Craig
Winton Churchill, +1
The proposal is where your experience becomes income

Jul 17, 2026

•

2 min read

The proposal is where your experience becomes income

A simple way to make your Upwork proposals stronger—and much faster to create.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Your Next Best Move May Be Smaller Than You Think

Jul 10, 2026

•

3 min read

Your Next Best Move May Be Smaller Than You Think

How to identify your current stage, recognize what’s working, and choose one clear next move.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Are You Designing Your Amazing Next Decade?

Jul 3, 2026

•

7 min read

Are You Designing Your Amazing Next Decade?

Most people are asking the wrong question about the years ahead. Here’s a better one.

Winton Churchill
Heidi Craig
Winton Churchill, +1
Download Your Amazing Next DecadeTM Diagram
LockSimple

Jul 2, 2026

•

2 min read

Download Your Amazing Next DecadeTM Diagram

Winton Churchill
Winton Churchill

Newsletter

Most People Don't Need More Experience...

Jun 26, 2026

•

2 min read

Most People Don't Need More Experience...

They Need to Make Their Experience Easier to Buy

Winton Churchill
Heidi Craig
Winton Churchill, +1

article

Is My Upwork Profile Too Long?

Jun 23, 2026

•

3 min read

Is My Upwork Profile Too Long?

Why the Most Qualified Professionals Often Lose Opportunities to People Who Simply Explain Their Value Better

Winton Churchill
Winton Churchill

Newsletter

The Experience Advantage: Turn What You Know Into Something People Can Buy

Jun 19, 2026

•

3 min read

The Experience Advantage: Turn What You Know Into Something People Can Buy

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

What If You Could Keep The Best Parts And Leave The Rest Behind?

Jun 12, 2026

•

2 min read

What If You Could Keep The Best Parts And Leave The Rest Behind?

Your experience still matters. Now you get to choose how you use it..

Winton Churchill
Heidi Craig
Winton Churchill, +1
Barefoot Consultants® Portable Income

Barefoot Consultants® Portable Income

Fun And Freedom Of Portable Income For People Over 50


Home

Posts

Authors

© 2026 Barefoot Consultants® Portable Income.
beehiivPowered by beehiiv