Entrepreneur or Bust: Why Workplace Survival in the 2020s Means Building a Portfolio Career

“Workplace survival in the 2020s basically means becoming an entrepreneur.”

That line has been echoing in my head for years now. Every month, every CoFlo coworking session, every client conversation, it gets louder.

This podcast + post is about why — and what you can actually do about it.

The Portfolio Economy, in Plain English

Economists have a sterile term for what’s happening: the portfolio economy.

I just call it reality.

We are shifting from a world where most people had one job and one employer to a world where people build portfolios of income streams — projects, gigs, advisory roles, side businesses, creative experiments.

Look at the numbers:

• In 2011, about 16 million Americans identified as independent workers. (MBO Partners)

• By 2023–2024, that number had risen to around 72–73 million — roughly 4.5× growth in just over a decade. (MBO Partners)

• That’s about 43–45% of the U.S. workforce doing some form of independent work. (GigEconomyData.org)

• McKinsey’s 2022 American Opportunity Survey found 36% of employed respondents — roughly 58 million people — identifying as independent workers, up from 27% in 2016. (McKinsey & Company)

If you run the math, independent work has grown at roughly double-digit compound annual rates over the last decade, while traditional W-2 employment has been basically flat by comparison.

We are very quickly heading toward a world where well under half of the workforce is full-time W-2 — and a majority of people have at least one independent income stream.

So if you’re still betting your entire life on one company, one boss, one paycheck…you’re playing last decade’s game with this decade’s stakes.

From “Climb the Ladder” to “Build the Web”

The old script was simple:

Go to school → get a job → climb the ladder at one company.

The new script looks nothing like that. It's more like:

Build the web.

You start stacking:

• client projects

• short-term contracts

• fractional roles

• creative experiments

• advisory work

• side businesses

  
  

…into a portfolio of income streams that makes you more resilient and more free than any single employer ever could.

This isn’t just a “freelancer thing” anymore. The data shows that a third to nearly half of working adults are already operating this way — whether they use the word “entrepreneur” or not.

Where I’m Seeing It Up Close: CoFlo

One place I see this shift most clearly is through CoFlo, the pop-up coworking community we host around New England.

If you’ve never heard me talk about CoFlo before, here’s the quick version:

• We host monthly pop-up coworking days — in places like Beverly, Portsmouth, Weymouth.

• People roll in with their laptops, their coffee, their chaos.

• And something subtle but powerful happens.

Yes, people show up to get work done. But they also show up with ideas.

In one room, you’ll see:

• remote workers

• creatives

• founders

• people between jobs

• people with jobs they clearly don’t want forever

You can almost watch the old model and the new model collide in real time.

Someone sits down and says:

“I’ve got this full-time thing, but I’m noodling on a podcast idea.”

Or:

“I’ve been sketching out a little SaaS tool.”

Or:

“I want to start something local, but I have no idea where to begin.”

Over time, CoFlo has organically become a kind of low-pressure incubator: a place where people can bring half-baked ideas, get honest feedback, meet collaborators, and feel that little jolt of:

“Oh wait… maybe I actually can build something.” 

Almost every session ends the same way — someone pulls me aside and asks:

• “How do we keep this going between events?”

• “Where do we share updates?”

• “How do I find that person I was vibing with about a food startup idea?”

What they’re really asking is:

“Where is the infrastructure for my next thing?”

They don’t just want a job. They want a place to work on their next thing — or their first thing. They want:

• a safe space to say, “Hey, I’ve got this idea.”

• a way to find the right humans to jam with.

• a way to take small steps without quitting everything tomorrow.

That’s the portfolio economy, up close. Not theory — behavior.

The Gig vs. Full-Time Growth Curve

Here’s why this matters so much.

If you compare the growth of independent work versus traditional full-time roles:

• Independent work has grown from 16M → 70M+ since 2011 — roughly 4–5× growth, around 10–12% CAGR over the period. (MBO Partners)

• McKinsey’s data shows the independent share of the workforce jumping from 27% → 36% between 2016 and 2022. (McKinsey & Company)

• Meanwhile, core full-time employment has inched along in the low single digits — and in some mid-skill categories, it’s shrinking as companies lean into automation and fractional talent instead.

In other words:

Gig / independent work is compounding; W-2 is crawling.

If you zoom out, the trend is obvious: Work is unbundling. Income is unbundling. Careers are unbundling.

The question isn’t “Will this happen?” It’s “How prepared will you be when it fully arrives?”

UnicornOS: An Operating System for Humans in This Shift

I’m not saying any of this from an academic distance. I’m in it.

Together with my partners at Unicorn Studios and Value Creation Labs, I’ve been building what we’re calling UnicornOS — an operating system for humans in this new world of work.

Not “an app.” Not a single product.

More like a stack:

• a mindset

• a set of tools

• support structures

• playbooks for idea people, independents, creatives, builders

  
  

…who want to thrive in this shift instead of getting steamrolled by it.

CoFlo is one of the ways we’re seeing this in the wild: real humans, real experiments, real proof that people want to build portfolio lives — even if they don’t have the vocabulary for it yet.

Yes, It’s Scary. But It Can Be a Massive Win.

Let’s be honest:

• Companies are shedding full-time roles.

• AI is reshaping what “work” even looks like.

• The old idea of “stability” is… kind of a joke right now.

But if we lean in and support each other, this era doesn’t have to be a horror story.

It can actually be a huge net positive:

• We can earn money in more flexible, creative ways.

• We can build things that feel aligned with who we are.

• We can design our time instead of being owned by it.

• We can surround ourselves with people who energize us instead of drain us.

That’s what I’m betting on.

That’s what UnicornOS is about.

And that’s why CoFlo and the other experiments we’re running matter so much to me — they’re little proof points that the portfolio economy is already here, living inside ordinary people’s lives.

A Personal Invitation

If any of this hits home —

If you’re building your own portfolio career, if you’re feeling that tug toward independence, or if you’re just trying to make sense of what the hell is happening to work right now…

I’d love to hear from you.

You can reach me directly at:

zach — with an h — at unicorn dot love

Tell me what you’re working on.What you’re struggling with.What you’re dreaming about.

I read every message. And I want Boston Speaks Up — and everything we’re building around UnicornOS — to actually serve you in this shift.

Because this rising tide we’re talking about?

If we do it right, it’s not just going to lift boats…

It’s going to wake up a lot of sleeping Unicorns.