From Dial-Up Days to Digital Paydays

Back in 1995

Picture this: I’m in San Diego, living the dream (sort of), working on the America’s Cup broadcast. MTV is at full steam.
“The Real World” is turning TV upside down eight strangers, one apartment, and the tagline:

Boom! Welcome, Reality TV.

So What?

That same year, I splurged on my first laptop a clunky Compaq that ate up my savings.

The internet meant dial-up, screechy modems, and AOL chat rooms that felt like intergalactic portals.
(You had mail. Sometimes. Eventually.)

Around this time, I had an idea: what if you made a show where people couldn’t leave their apartment and had to live entirely online?

Wild, right?

In a pre-Uber Eats, pre-Amazon Prime world, buying toilet paper online sounded as futuristic as the Jetsons.
(Sci-fi cartoon family, for those too young to remember.)

The Real World... Now

Fast forward.

Forget laptops your freaking phone runs your life now.

That “speculative” premise? It’s just… Tuesday.

Pandemic hits. Suddenly, remote work, digital nomads, and the gig economy aren’t fads they’re baseline reality.

Upwork, Fiverr, and a bazillion apps let you work (and overshare) from anywhere.

Whole professions from coaching to coding to content creation exist entirely online now.

From There To Here

1995 looked like this:

• Slow, glitchy internet

• Laptops cost as much as a used car

• No such thing as remote work

• Needed a fax machine and an office to do “real” work

But now:

• Your phone is a fully loaded opportunity machine

• Remote work isn’t just possible, it’s expected

• Building a business, selling your expertise, teaching totally doable solo

• You can invest, trade, and build your personal brand in your pajamas

Laptop Survivor 2025

If I pitched my ‘95 idea today, maybe it’d be called Laptop Survivor 2025.

Contestants could DoorDash dinner, hop between gigs in Sydney and Seattle, or go viral while brushing their teeth.

But let’s be honest not everything’s an upgrade: distraction, doom-scrolling, and lonely lunches are now part of the “game.”

Your World, Your Terms

Maybe you’re three-quarters up the corporate ladder, looking out and wondering, “Did I miss my shot?”

Listen:

It’s not too late to build your own ‘real world,’ using the tools you already have (and a few you haven’t tried yet).

We’re entering solo-entrepreneur Season 2.

AI isn’t here to steal your job it’s here to hand you a toolkit and say, “Go nuts.”

Your work experience + new tech = something powerful, if you’re willing to experiment.

Try This:

• What’s one possibility exciting or terrifying that you’d explore if nobody was watching?

• Could you launch a side hustle, try remote consulting, or start selling your expertise online?

Not sure? Dip a toe:

• Sign up on a freelancer platform

• Take an online course

• Try to earn even a dollar online

I’ll never forget the first time I did, it felt like magic money.

It’s never too late to start exploring what’s possible.
Stop waiting for permission.

The world is your apartment.
And this time, you control the camera.