Years ago, newspapers had a certain logic to their classified sections.

The lower-paying jobs tended to be up front. As you worked your way through the section, you eventually got to the jobs requiring more experience, more responsibility—and paying considerably more money.

Today, I hear a modern version of the same complaint all the time:

“I looked online, and all I saw were low-paying jobs.”

My slightly smart-aleck response is:

Quit looking in the low-paying jobs section.

Because there is something important happening here that is easy to miss.

The Internet isn't just a place to find work.

It's one of the greatest market-research databases ever created.

And if you're over 50 and trying to figure out how your experience might translate into portable income, that distinction matters enormously.

Suppose you've spent 25 or 30 years solving operational problems.

Maybe you've improved processes, trained people, rescued projects, dealt with unhappy customers, reduced errors, organized events, worked through regulatory issues, built systems, or figured out why things kept falling through the cracks.

You might have an idea for turning some of that experience into income.

That's good.

But a good idea isn't yet a market.

You can ask your friends:

“Do you think businesses would pay somebody to do this?”

And they'll probably say:

“That sounds great, Winton. You should do it!”

They're your friends.

They're supposed to say things like that.

What I want instead is evidence.

Are real people already asking for help with this problem?

Are they putting money behind it?

Are they spending $500?

$2,000?

$5,000?

Are companies hiring the same type of person repeatedly?

Those answers are much more useful than encouragement.

This is where people with decades of experience often get tripped up.

They go online and search for the title they used to have.

“Operations Manager.”

“Regional Director.”

“Human Resources Manager.”

“Vice President of Whatever.”

That may completely miss the opportunity.

Businesses usually don't wake up one morning saying:

“We desperately need some process optimization.”

They say:

“Everything is falling through the cracks.”

Or:

“We've grown too fast and nobody follows the same process.”

Or:

“The owner is still doing everything.”

Or:

“We're losing customers and can't figure out why.”

That's the language of a problem.

And problems are where the money is.

The bigger question isn't:

Could I get this job?

It's:

What is happening inside this organization that caused them to go outside the company and ask for help?

Maybe somebody left.

Maybe they grew too quickly.

Maybe they don't have the expertise internally.

Maybe they know exactly how to solve the problem—but nobody has the time.

That last one is especially interesting.

A business owner may be perfectly capable of doing a task themselves.

But if their time is better spent developing products, finding customers, managing employees, or making major decisions, hiring someone experienced to take that problem off their plate makes perfect economic sense.

This is where age can become an advantage rather than a liability.

A less-experienced person may have to figure out the common mistakes in an industry.

You've already seen them.

They may need to discover what happens when a project starts going sideways.

You've watched it happen before.

They may need to research five possible solutions.

You may already know which four probably won't work.

There is tremendous value in being able to listen to somebody explain a difficult situation and say:

“I've seen this before.”

You aren't saying their problem is identical.

You're saying you've seen enough situations over enough years to recognize the pattern.

That can save a client weeks—or months—of figuring it out themselves.

And that is very different from selling an hour of your time.

You're selling the shortcut created by experience.

Here's an exercise I gave our Tuesday Night group this week.

Pick one thing you think you might be able to help someone with.

Then go hunting for evidence.

Find five to ten examples of actual buyers asking for that kind of help.

Don't apply yet.

Just study them.

Pay particular attention to:

• The exact words they use to describe the problem.

• The outcome they're trying to achieve.

• What happens if they don't solve the problem.

• How much they're willing to spend.

• Whether the buyer regularly hires outside experts.

You're not trying to prove that your idea is wonderful.

You're investigating.

And a red light is useful.

If nobody seems to be paying for something, perhaps that's not the direction to pursue.

Wonderful.

You just saved yourself six months.

But sometimes you'll discover something very different.

You'll realize that companies aren't merely paying for the thing you know how to do.

They're paying substantial amounts of money for it.

And often that first project is simply the doorway.

A modest assignment can lead to a larger project.

The larger project can lead to recurring work.

Recurring work can lead to introductions to other people with the same problem.

Suddenly you aren't looking for “freelance jobs.”

You're building a small portfolio of clients who value something you already spent decades learning how to do.

That is a completely different game.

And for many people in their 50s, 60s and 70s, it's a much better one.

You don't need to convince the world that your experience has value.

You need to find the places where the marketplace is already saying:

“We need someone who knows how to do this.”

That's where I'd start.

—Winton and Heidi

P.S. This Saturday we're back with the next Amazing Next Decade workshop, where we'll take the work from Sessions 3 and 4 and make it practical. Bring one or two possible directions you're considering. We're going to work on turning those possibilities into evidence.

P.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.