🎉 Day 500 is coming! On August 28, 2026, Nomads 50+ turns 500 days old, and the Next Chapter annual membership goes from $50 to $99. Join before then to lock in $50/year and come along for everything I’m building next.
She actually liked her job.
Then she got laid off.
She had just turned 50, her industry was shrinking, and suddenly 10,000 people from the same company were entering the job market alongside her.
That was the wallop.
Instead of immediately trying to recreate the career she’d just lost, Colleen decided to try something she knew almost nothing about:
Building an online business.
Eight years later, that decision has given her something she didn’t even realize she was building toward at the time.
Freedom.
As Colleen puts it, she’s now “free to move about the cabin.”
And she’s taking that literally.
When we recorded this conversation, the boxes were behind her. Her apartment lease was ending. Her first five-week house sit in New Hampshire was already lined up.
Colleen was about to become a nomad.
If you’ve been enjoying Nomads 50+ and are seriously considering this next chapter, consider becoming a paid subscriber. You’ll get full access to every in-depth city guide, each Sunday Spark business idea, and the upcoming Recalibrate50+—a structured, ongoing guide to help you move from dreaming about your next chapter to designing it carefully and confidently. Your support keeps this publication independent, ad-free, and focused on helping adults redefine what life after 50 can truly look like.
The Business Came Before the Nomadism
I think this is one of the most interesting parts of Colleen’s story.
She didn’t decide to become a digital nomad and then scramble to figure out how to fund it.
She built the portable income first.
When the opportunity to become nomadic eventually appeared, the economic infrastructure was already there.
But building it wasn’t easy.
Colleen had writing experience from earlier in her career, but almost everything about online business was new to her.
Funnels?
She didn’t know what they were.
Email service providers?
She wondered if people meant Gmail.
She learned WordPress. She learned Kajabi. She took courses. She experimented with different business models.
Her first idea was an online magazine for her local community.
It taught her an enormous amount about building an online business.
It also taught her something else:
An online business isn’t necessarily a location-independent business.
If your customers, content and revenue are tied to one town, you’ve essentially created a digital version of a brick-and-mortar business.
Then life changed again.
Colleen’s husband became ill. She became his caregiver, and he died about a year later.
Suddenly the question wasn’t merely how to make money online.
It was what kind of life she wanted to build next.
Turning Decades of Experience Into Digital Income
As Colleen learned the mechanics of online business, other women began asking her how she was doing it.
That revealed the opportunity that would eventually become her business:
Helping women over 50 turn what they already know into digital income.
Not necessarily inventing something completely new.
Not becoming technology experts.
Not building venture-backed startups.
Taking accumulated knowledge, skills and experience and packaging some portion of it into something other people will pay for.
That might mean consulting.
A digital product.
A membership.
A workshop.
A Substack.
User-generated content.
A course.
Or something else entirely.
Colleen has experimented with many of them herself.
And that experimentation produced one of the most useful ideas in our conversation.
Your First Idea Doesn’t Have to Be Your Best Idea
People frequently get stuck because they believe their first business idea needs to be the idea.
Colleen argues almost the opposite.
You need an idea.
It probably won’t be your final one.
It may not even be particularly good.
That’s okay.
Its first job is to teach you how the machinery works.
Colleen recommends starting with an extremely narrow problem and creating a simple digital product around it.
Not:
“How to become a digital nomad.”
Something closer to:
“How to decide what to sell, donate, and store before becoming a nomad.”
Small.
Specific.
Solvable.
Her rule is wonderfully practical:
Your first digital product shouldn’t take more than an afternoon to create.
Because you’re not trying to build your empire yet.
You’re trying to learn.
Sell It Before You Spend Six Months Perfecting It
This part of our conversation reinforced something I think many aspiring entrepreneurs over 50 desperately need to hear.
Don’t spend six months building the giant course.
Build the small thing.
Put it in front of people.
Ask them to buy it.
Then watch what happens.
If nobody buys your $19 guide, you’ve learned something.
Maybe the problem isn’t important enough.
Maybe your positioning isn’t clear.
Maybe the audience isn’t right.
Maybe the marketing is wrong.
Maybe the product needs to change.
That’s useful information.
But you only get that information once something enters the market.
As Colleen puts it, you need the product to get the data.
That’s a radically different approach from sitting at home attempting to design the perfect business in your head.
It Took 18 Months
There’s another important dose of reality in this episode.
Colleen didn’t start her online business and immediately replace her corporate salary.
She had roughly a year of severance, which gave her breathing room.
But even that wasn’t enough to completely establish the business.
She says it took around 18 months before she began understanding the level of effort and activity required to produce a sustainable level of income.
That’s important.
The internet is filled with stories about overnight businesses.
Colleen’s experience is much more useful.
You learn.
You experiment.
You build an audience.
You make mistakes.
You refine the offer.
You market.
You discover what people actually want.
Then, eventually, you understand the machine well enough to operate it deliberately.
The Empty Theater Problem
Perhaps my favorite analogy from Colleen is what she calls the empty theater problem.
You’re standing on stage.
You perform.
Nobody is there.
So you come back tomorrow.
Still nobody.
Eventually one person arrives.
Then another.
Then somebody tells somebody else.
And eventually the theater begins filling.
Colleen lived this herself.
After roughly eight years online, she had around 3,000 Instagram followers.
Then something changed.
One video took off.
Within roughly four months, she grew to around 53,000 followers.
Her explanation isn’t a clever algorithm hack.
She kept showing up.
In fact, at the time of our conversation, Colleen said she had done a live video every day for more than 600 days.
That’s a very different message from “make $10,000 by Sunday.”
Sometimes the breakthrough arrives because you were still standing on the stage when the audience finally walked in.
Ninety Percent of the Job Is Marketing
Colleen estimates that when she’s working, roughly 90 percent of her time is marketing.
That’s another uncomfortable reality of entrepreneurship.
People imagine they’ll start an art business and spend their days making art.
Or create a consulting business and spend all their time consulting.
Or write a book and spend their time writing.
But when you own the business, a huge portion of your job becomes finding, attracting and communicating with customers.
Colleen learned this firsthand.
You can build the product.
You can put it in a store.
You can create the membership.
But if nobody knows it exists, nothing happens.
She puts it very simply:
You can’t talk about your thing too much.
Experience After 50 Is the Raw Material
One of the strongest ideas in our conversation is also central to Nomads 50+.
If you’re over 50, it’s almost impossible that you’ve reached this point without accumulating something valuable.
Maybe it’s professional expertise.
Maybe it’s a hobby.
Maybe it’s something you’ve repeatedly solved for other people.
Maybe it’s knowledge so familiar to you that you’ve stopped recognizing it as expertise.
Colleen works with attorneys, consultants, professionals and people from all kinds of backgrounds.
Some want to monetize what they already did professionally.
Others want nothing whatsoever to do with their previous career.
Both can work.
The objective isn’t necessarily to reinvent yourself.
It’s to examine what you already know and ask:
What problem can I solve for someone else?
Then start there.
Build the Exit Ramp Before You Need It
Colleen says roughly 90 percent of the people she works with are still employed.
I think that’s significant.
They aren’t waiting for retirement.
They’re building an exit ramp.
They’re experimenting with ideas while they still have their salaries.
They’re learning digital tools.
They’re figuring out marketing.
They’re building audiences.
They’re discovering which skills people will pay for.
So when retirement, a layoff or another wallop arrives, they’re not starting from zero.
That’s probably one of the smartest forms of career insurance available today.
And Now She’s Going Nomadic
Colleen’s business has evolved alongside her life.
Now she’s taking the next step.
She’s giving up her apartment and beginning with house and pet sitting, which dramatically reduces one of the largest costs of travel: accommodation.
Her first extended sit came through someone who discovered her online.
After that?
She doesn’t entirely know.
New Hampshire first.
Possibly Florida.
Eventually Germany, France, Scotland, Scandinavia, Mexico and wherever else looks interesting.
She’s deliberately keeping the plan loose.
Because the business she spent years building can come with her.
That’s the real payoff.
Not passive income.
Not lying on a beach while money magically appears.
Optionality.
The ability to decide where you want to be next without first asking whether your job will allow it.
In this episode, Colleen and I talk about:
Getting laid off just after turning 50
Starting an online business with almost no technical knowledge
Why her first online business wasn’t actually location independent
Becoming a caregiver and later a widow
Turning experience into digital income
Why your first business idea doesn’t need to be your final one
Starting with tiny digital products instead of giant courses
Why it took around 18 months to build sustainable momentum
The “empty theater” problem of building an audience
Going from roughly 3,000 to 53,000 Instagram followers in months
Showing up live for more than 600 consecutive days
Why marketing may become 90 percent of your work
Memberships, workshops, digital products and Substack
Building multiple income streams
Why “passive income” is largely a myth
Finding an extremely narrow problem to solve
Pricing digital products around the value of the solution
Why people over 50 already possess monetizable knowledge
Building a side business before retirement
House sitting as a way to dramatically reduce nomadic living costs
Becoming a nomad without having every destination planned
And why simplicity often beats sophistication when you’re starting
Colleen didn’t know when she was laid off at 50 that she was beginning the process of becoming location independent.
She just took the next step.
Then another.
Then another.
Eight years later, she’s packed the boxes.
Now she’s taking the business with her.
That’s what an exit ramp looks like.
If you’re looking for practical ways to build location-independent income, the Sunday Spark Action Pack Library is a great place to start. Each guide is a focused, in-depth business blueprint designed specifically for Nomads 50+, covering the business model, startup steps, realistic income potential, tools, and common pitfalls. These aren’t quick blog posts—they’re structured action packs you can actually use. At just $2.99 each, they’re an easy way to explore new opportunities and turn your experience into something portable. Explore the Sunday Spark Action Pack Library and see what might spark your next chapter.
