Gen X Is Quietly Dominating the Gig Economy, and TikTok Doesn't See It Coming

Let me take you back for a second…

The year was 2012.

Age: 40.

Here was my morning routine:

Open my eyes.

Groan.

Shuffle to the shower.

Shuffle to the car.

Shuffle into work like a zombie who forgot its purpose.

Around 10 a.m., the daydreams kicked in.

Being anywhere but there. Doing anything but that job.

Then I’d feel guilty for wanting more and force myself not to open a browser tab and work on my exit plan (I believe the kids call this quiet quitting these days).

Rinse and repeat for months.

When people talk about feeling “stuck,” I get it. I lived it.

Most of the Gen Xers who reach out to me over the past 13 years until now? They’re in the same boat I was in back then.

They want out…

BUT they also want to keep their health insurance, their mortgage, and their sanity.

They don’t want to spend four years earning another degree…

But they also don’t want to quit cold turkey and hope the universe sends a miracle.

They need a middle path.

Back then, mine ended up being Upwork. Today, the entire Gig Economy has exploded, making that middle path even more viable for Gen Xers.

Turns out, I was WAY ahead of my time because Gen Xers are now flooding into freelancing…

Here’s what’s happening behind the scenes:

Translation?

Corporate America isn’t building big teams anymore. They’re outsourcing everything they can.

And they want adults. People with experience. People who won’t disappear halfway through a project.

That’s us.

We’re in the sweet spot and most Gen Xers don’t even realize it.

Last year I tested Upwork for 30 days just to make sure it still worked.

Here’s what happened:

Not bad for something I can’t dedicate a ton of time to - because I still have a business to run and I need to write email mixtapes like this for you (which is love doing BTW… thank you for reading).

But the real lesson?

Gen X is built for this stuff.

We show up.

We know how to fix things when instructions make zero sense.

We survived dial-up, AOL CDs, and printers with personalities.

Clients notice that.

One even said I had “panache.”

Still funny to me.

My friend Erica runs a Skool community called Freelance With Erica ($), and the results inside the group are wild.

Here’s one screenshot I grabbed:

Steph got laid off → landed two contracts + a 5-star review in less than a week.

That’s not magic. That’s what happens when someone gives you a simple system, real feedback, and a path to your first paying client.

A lot of people ask me how to start freelancing.

If I had something like this in 2012, I wouldn’t have stayed stuck as long as I did.

Here’s why I like her program:

I’ve never seen anyone else offer that.

It’s the cleanest, lowest-risk freelancing shortcut for Gen Xers who want options but don’t want to throw their life into chaos.

👉 Try Freelance With Erica ($)

Even one small freelance win changes your brain.
You go from “I’m stuck” to “Oh… I can do this.”

And that’s the moment everything shifts.

If I boil all this down, here’s what matters:

Third Eye Blind - “Semi-Charmed Life”

He’s talking about drugs but I think the song could be a metaphor for doing work you don’t want to be doing.

The paycheck, the routine, and the health insurance each give you that little bump" of “everything’s fine.”

But the tradeoff hits you later.

The slow fade, the feeling that you’re losing pieces of yourself just to make it to Friday.

That’ll do it for these week. Now, go check out Erica’s course. Seriously!

Have a good one,

Corey