Good morning,
Years ago, one of my bosses said something to me that was both insulting and surprisingly accurate.
“Churchill, I don’t know why we hired you, and I really don’t know what you do.
I just know that when a bunch of people are at each other’s throats, if I send you in for a month or two, they’ll be laughing and talking to one another again. And that’s worth whatever we pay you.”
It was one of the more satisfying insults I’ve ever received.

At the time, I might spend Monday and Wednesday in a suit and tie, talking with people in marketing, corporate operations, and manufacturing.
The rest of the week, I would be in jeans and sneakers, talking with graphic artists, creative writers, and programmers.
My real job was translating between the suits and the creative and technical people—groups that occasionally seemed to be communicating through opposing legal teams.
That ability never appeared neatly in my job title.
But it solved an expensive problem.
And that is where Heidi and I see many people over 50 underestimating the value of their experience.
They tell us:
“I was a nurse.”
“I worked in operations.”
“I was in human resources.”
“I was a teacher.”
Those titles may be accurate, but they are woefully incomplete.
A nurse may also know how to train new employees, improve medical records, communicate with frightened families, spot dangerous inconsistencies, and keep a complicated process moving when the building is full of people having one of the worst days of their lives.
An operations manager may know how to straighten out vendors, document procedures, onboard employees, repair broken workflows, and get six people who disagree with one another moving in approximately the same direction.
And, as Heidi pointed out during our Tuesday night call, many of those abilities travel remarkably well.
If you managed vendors in construction, you may be able to manage vendors in several other industries.
If you coordinated projects in real estate, your ability to organize people, deadlines, decisions, and details doesn’t suddenly disappear when the subject matter changes.
The market doesn’t buy your old job title.
It buys pieces of what you learned to do.
That distinction matters because many experienced people believe they must reinvent themselves before they can earn money independently.
Usually, they don’t.
They need to look underneath the title and identify the problems people repeatedly trusted them to solve.
Finish this sentence:
People always came to me when they needed someone to ____________.
Don’t make it sound impressive. Make it true.
Maybe you calmed down unhappy customers.
Maybe you found mistakes everyone else missed.
Maybe you could take a chaotic project and determine what needed to happen next.
Maybe you explained complicated things without making people feel stupid—which, we can assure you, is a rarer and more valuable skill than many advanced degrees.
One caution: just because you can do something doesn’t mean it belongs in your next chapter.
I know how to jump into a troubled software project and get 15 people working together. I am far less interested in spending my next decade doing it. It involves too many late nights, too many difficult conversations, and far too many airports.
The goal is to find the intersection between:
What you are good at.
What someone will pay for.
And what you would still enjoy doing.
Your next opportunity may not require becoming someone new.
It may begin by finally recognizing what people have valued about you all along.
Hit reply and complete this sentence for us:
People always came to me when they needed someone to ____________.
We would like to hear your answer.
Winton & Heidi
P.S. If this idea of designing the life first—and then figuring out the income that fits it—struck a chord, that’s exactly what we’re working through right now in our 6-Week Freedom Protocol Challenge.
We had our second Tuesday session this week, and Saturday at 10:00 AM Central is the hands-on workshop portion, where Heidi and I will work directly with participants on their questions, ideas and next steps.
If you missed Tuesday, that’s fine. Every Tuesday and Saturday session is recorded, and you’ll have permanent access to the recordings inside your Freedom Protocol course.
The complete 6-week Challenge is $197, or 4 monthly payments of $49.95.


