One of the hardest things about starting over professionally is that we tend to look at ourselves through the lens of our old job titles.

“I was a project manager.”

“I spent 25 years in healthcare.”

“I worked in operations.”

“I was in HR.”

“I ran a small business.”

And then comes the question:

Who would hire someone like me?

I think that’s the wrong question.

In fact, it may be one of the questions that keeps experienced people stuck the longest.

Because the marketplace is rarely sitting around looking for “someone like you.”

People are looking for someone who can solve a problem.

A job title is just shorthand.

Behind it may be 20, 30, or 40 years of things you learned how to do:

You calmed down angry customers.

You trained new employees.

You spotted mistakes before they became expensive.

You organized chaotic projects.

You figured out why things kept falling behind.

You dealt with difficult personalities.

You made complicated information understandable.

You knew when something didn’t look right—even when you couldn’t immediately explain why.

And perhaps most important:

You developed judgment.

That’s one of those assets that rarely appears on a résumé.

But it can be enormously valuable.

Judgment comes from having seen the movie before.

Sometimes many times.

Instead of asking:

Who would hire someone like me?

Try asking:

That question takes you someplace entirely different.

Suppose you spent years in operations.

You might think your marketable skill is “operations management.”

Maybe.

But buyers usually don’t wake up saying:

They say things like:

“Our projects keep running late.”

“Training new people takes forever.”

“Nobody follows the same process.”

“Everything is in people’s heads.”

“I can never get away from the business.”

Those are problems.

And somewhere behind each one may be a perfectly good consulting or freelance project.

This is one of the simplest ways I know to think about portable income:

They have a thorn in their paw.

If you know how to remove it, you may have something valuable.

Sometimes the thorn is costing them money.

Sometimes it’s consuming time.

Sometimes it creates risk.

Sometimes there’s a deadline attached to it.

Sometimes it’s simply driving them crazy.

And the greater the consequence of leaving the problem unsolved, the more valuable the solution can become.

There’s a big difference between:

“Can you clean up this document?”

and:

“Can you review this before we submit it to the regulator?”

Some of the underlying skills might be similar.

The stakes are not.

That matters.

Imagine someone who spent 25 years as a nurse.

At first glance, she may think:

“I don’t want another nursing job, so what can I possibly do?”

Quite a lot.

Her experience might translate into:

Clinical documentation review.

Patient education materials.

Healthcare training.

Medical content review.

Health-app consulting.

Process and compliance work.

The interesting part is that she doesn’t necessarily need someone searching for a “retired nurse.”

A health technology company might need someone who can tell them whether their patient instructions actually make sense.

A medical practice might need help reviewing clinical documentation.

A healthcare publisher may need someone who can translate complex medical information into language normal human beings can understand.

Same experience.

Different buyer.

Different problem.

Different market.

That’s the shift.

There’s another distinction here that becomes increasingly important as we get older.

A younger person may know how to perform a task.

An experienced person may know when something is about to go wrong.

That difference can be worth a lot.

You recognize patterns.

You notice trouble earlier.

You know which questions to ask.

You know when the seemingly obvious solution probably isn’t going to work.

You’ve already made some of the mistakes.

And survived them.

That means the distance between problem and solution can become much shorter for you than it is for someone encountering the situation for the first time.

That’s what experience buys.

Pick one thing you know how to do well.

Not ten.

One.

Then answer these four questions:

Then try completing this sentence:

I could help __________ who struggle with __________ by helping them __________.

For example:

I could help growing professional-service firms that struggle with inconsistent processes by creating simple procedures their teams can actually follow.

That’s much closer to a market than:

“I have 25 years of operations experience.”

You can even use ChatGPT as a thinking partner.

Ask:

“Identify 10 types of buyers who might pay someone with this expertise.”

Then:

“How would those buyers describe the problem in their own words?”

And:

“What would make solving this problem financially important to them?”

You’re not asking AI to decide your future.

You’re using it to help you see possibilities you may have overlooked.

This may be the part people miss.

You don’t need to dominate an industry.

You may need four $500 projects a month.

Or one solid recurring client and a handful of smaller projects.

Or three specialized advisory clients.

Or one $1,500 problem you solve twice a month.

Portable income doesn’t have to look like a traditional career.

That’s the point.

You can build the work around the life you want instead of automatically building your life around the work.

And you are not choosing what you’ll do for the rest of your life.

You’re choosing a place to start.

Your professional history is valuable.

But the market doesn’t pay you simply because you accumulated experience.

It pays when that experience becomes useful to someone else.

So this week, forget the title for a moment.

Forget the résumé.

Forget trying to explain everything you’ve ever done.

Look for the thorn.

Then ask:

That’s where some very interesting possibilities begin.

—Winton and Heidi

P.S. If you’re still trying to figure out which parts of your background could translate into portable income, start with our What Could I Possibly Do Online? questionnaire. It was built specifically to uncover the skills, experience, knowledge, and judgment that are often hiding behind your old job titles.

And if you’ve already completed it, pull your report back out this weekend and choose just one possibility. Run it through the four questions above. You may see an opportunity you completely missed the first time.