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Oliver Buchannon
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.

Why Experienced Professionals Are Winning in the New Freelance Economy

Mar 13, 2026

•

5 min read

Why Experienced Professionals Are Winning in the New Freelance Economy

What AI is really doing to the freelance market (and why experience matters more than ever)

Winton Churchill
Heidi Craig
Winton Churchill, +1
The #1 Reason Experienced Professionals Get Overlooked

Mar 6, 2026

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4 min read

The #1 Reason Experienced Professionals Get Overlooked

It’s not lack of skill. It’s something far easier to fix.

Winton Churchill
Heidi Craig
Winton Churchill, +1
If You’ve Been Stuck Lately...

Feb 27, 2026

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2 min read

If You’ve Been Stuck Lately...

You don’t need more discipline. You need a smaller next step.

Winton Churchill
Heidi Craig
Winton Churchill, +1
If You Don’t Define Boundaries, Clients Will

Feb 20, 2026

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3 min read

If You Don’t Define Boundaries, Clients Will

Structure your work so your time, energy, and income stop leaking.

Heidi Craig
Winton Churchill
Heidi Craig, +1

proposals

+1

Why Bidding on a Complex Consulting Job Is a Fool’s Errand (Unless You Sell the First Hour)

Feb 18, 2026

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6 min read

Why Bidding on a Complex Consulting Job Is a Fool’s Errand (Unless You Sell the First Hour)

Winton Churchill
Winton Churchill
The Simple Shift That Stabilizes Your Portable Income

Feb 13, 2026

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4 min read

The Simple Shift That Stabilizes Your Portable Income

How to Stop Starting Over with New Clients

Winton Churchill
Heidi Craig
Winton Churchill, +1
Pricing Your Services with Confidence (and Why Silence Is Your Secret Weapon)

Feb 6, 2026

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4 min read

Pricing Your Services with Confidence (and Why Silence Is Your Secret Weapon)

Winton Churchill
Winton Churchill
Your Next 90 Days (Without Overwhelm)

Jan 30, 2026

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3 min read

Your Next 90 Days (Without Overwhelm)

Heidi Craig
Winton Churchill
Heidi Craig, +1
Why effort isn’t your problem

Jan 23, 2026

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7 min read

Why effort isn’t your problem

and what actually is

Heidi Craig
Winton Churchill
Heidi Craig, +1
Quick reality check about getting your first paid jobs
LockSimple

Jan 17, 2026

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4 min read

Quick reality check about getting your first paid jobs

Why most smart people stall — and how we fix that

Winton Churchill
Heidi Craig
Winton Churchill, +1
A simpler way to get clients in 2026

Jan 9, 2026

•

5 min read

A simpler way to get clients in 2026

Built on clarity, trust, and what you already know

Winton Churchill
Heidi Craig
Winton Churchill, +1
3 Things That Will Matter Most In 2026

Jan 2, 2026

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5 min read

3 Things That Will Matter Most In 2026

And how to position yourself for success

Winton Churchill
Heidi Craig
Winton Churchill, +1
The Fastest Way to Upgrade Your Output
LockSimple

Dec 30, 2025

•

2 min read

The Fastest Way to Upgrade Your Output

This is the unfair advantage

Winton Churchill
Winton Churchill
Boxing Day isn’t random (here’s why)
LockSimple

Dec 29, 2025

•

2 min read

Boxing Day isn’t random (here’s why)

A small window that creates a big advantage

Winton Churchill
Winton Churchill
If you only do ONE thing this year...
LockSimple

Dec 27, 2025

•

4 min read

If you only do ONE thing this year...

Practical knowledge you’ll actually use — and your clients will thank you.

Winton Churchill
Winton Churchill
2025 Changed the Game for 50+ Freelancers

Dec 26, 2025

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5 min read

2025 Changed the Game for 50+ Freelancers

Here’s what shifted — and how to ride it into 2026

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

The Great Holiday Q+A - Unplugged

Dec 20, 2025

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11 min read

The Great Holiday Q+A - Unplugged

Don't let questions hold you back. We've got bubbly... and answers!

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

How to Navigate Your Client’s AI Preferences

Dec 12, 2025

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12 min read

How to Navigate Your Client’s AI Preferences

...while still leveraging the tools that make you faster, better, and more competitive

Winton Churchill
Heidi Craig
Winton Churchill, +1
Infographic: Creating Effective Portfolio Items

Dec 11, 2025

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1 min read

Infographic: Creating Effective Portfolio Items

Tuesday Night Infographic

Winton Churchill
Heidi Craig
Winton Churchill, +1
Your Year-End Boost: The 7 Strategies That Set You Up to Win

Dec 5, 2025

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11 min read

Your Year-End Boost: The 7 Strategies That Set You Up to Win

Download inside!

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Grateful, Growing, and Getting Paid This Week in Portable Income

Nov 28, 2025

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7 min read

Grateful, Growing, and Getting Paid This Week in Portable Income

A holiday-sized dose of clarity + your downloadable superpower list

Winton Churchill
Heidi Craig
Winton Churchill, +1
The shutdown ended... your plan B shouldn’t wait

Nov 27, 2025

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3 min read

The shutdown ended... your plan B shouldn’t wait

Replay + Black Friday Special

Winton Churchill
John Meskel
Winton Churchill, +1

Newsletter

Better Mood, Better Work: The Freelancing Multiplier You’re Overlooking

Nov 21, 2025

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9 min read

Better Mood, Better Work: The Freelancing Multiplier You’re Overlooking

Why your best freelance work starts before you touch the Keyboard

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

Get Ready to Streamline Your System

Nov 14, 2025

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10 min read

Get Ready to Streamline Your System

Cut your time investment and multiply your odds of landing a client.

Winton Churchill
Heidi Craig
Winton Churchill, +1

Newsletter

They Did It — So Can You!

Oct 31, 2025

•

9 min read

They Did It — So Can You!

This week’s real success stories show it’s possible — next week’s live demo shows how to manage it like a pro.

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

Barefoot Consultants® Portable Income

Fun And Freedom Of Portable Income For People Over 50


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