From Layoff Shock to Startup Spark: 7 Reinvention Plays for the AI Job Squeeze

Portfolio careers, fractional leadership, and the rise of the self-authored professional.

There’s a moment after a layoff that feels like freefall. Not the email or suspicious calendar invite from HR that pops up unexpectedly, that part feels strangely out-of-body, like watching a version of yourself from above.

The real shock comes later. When the laptop is surrendered. When Slack access expires. When the noise stops and the world finally goes quiet and you hear your own thoughts again for the first time in years.

That silence?
It isn’t empty.
It’s a doorway.

I know because I walked through it the week before Thanksgiving 2023, exactly two years ago. What felt like collapse became ignition. What felt like loss became space. What felt like an ending became the beginning I didn’t know I needed.

In today’s marketplace, reinvention is structural. The ground beneath the job market is shifting in real time, and it’s not slowing down. We are entering a new era of work shaped by two unstoppable forces:

1. The AI job squeeze: entire functions replaced, not just roles (McKinsey, 2023).
2. The rise of portfolio careers: people becoming their own small economies (BLS self-employment projections, 2024).

What happened to me is now happening to millions.

And yes, people are whispering about an AI bubble. Just this month, Peter Thiel’s hedge fund sold its entire ~$100M Nvidia stake in Q3 2025 (SEC 13F filings). SoftBank dumped its $5.8B position in the same quarter (Nikkei, Sept 2025).

These aren’t random moves. They’re smoke signals from the deepest pockets in tech.

And moving into this next era, the people who will thrive aren’t the ones with perfect résumés, or linear paths. They’re the ones courageous enough to reinvent, expand, and build careers with multiple lanes, not just one.

You’re not late.
You’re right on time.

Is This the Next Dot-Com Bubble? Lessons From 2000 (And How to Protect Yourself)

We’ve been here before.

In 1999–2000, the internet was supposed to change everything. And it did, but the timing and economics were wrong. Valuations exploded.

• The Nasdaq fell 78% between March 2000 and October 2002 (Federal Reserve).

• Pets.com burned through $82M and collapsed in 9 months (WSJ archives).

• Trillions in market value evaporated.

And yet, the survivors became the backbone of the next economy: Amazon, eBay, Google.

2025 parallels are eerie:

• The “Magnificent Seven” now make up 33%+ of the S&P 500, a concentration higher than at the dot-com peak (Goldman Sachs, 2025).

• AI spending is outpacing near-term revenue (Morgan Stanley Cloud Capex Analysis, 2025).

• Companies are overbuilding data centers the way telecoms overbuilt fiber in the 90s.

• Smart money exiting, as noted above: Thiel, Softbank, despite trillion dollar valuations.

Key lesson: Bubbles burst. But the technology survives.

The winners are those who treat AI as infrastructure, not hype.

If (when?) an AI correction hits, the layoffs we’re seeing now will look mild. But the opportunity on the other side will be massive for those who are ready.

Your playbook: Build multiple income streams now, own your audience, and treat AI as a tool, not a replacement. The people who treated the internet as infrastructure in 2001 became the trillion-dollar companies of today. We need to do the same with AI.

The Old Career Ladder Is Gone

(And it’s not coming back. We all need to move on and get over it. The ladder was kind of broken anyway.)

We were raised on a formula: work hard → get promoted → stay loyal → climb the ladder.

But ladders breed politics, gatekeeping, and fragility. Ladders require stability, and stability no longer exists in modern work.

Today’s career landscape is nonlinear and diversified:

• Contract work

• Fractional leadership

• Consulting + advising

• Teaching + speaking

• Creative production

• Brand partnerships

• Digital products

• Side businesses

• Personal brand building

Independent work is growing 3x faster than traditional employment (Upwork Report, 2024).

We’re not employees anymore. We’re ecosystems.

Companies have changed too:

• They want expertise, not headcount (Gartner CHRO Insights, 2024).

• They want flexibility, not pensions.

• They want fractional leaders, not middle managers.

Nothing is “wrong” with you if the ladder didn’t work.
The ladder became irrelevant.

The people who accept that fastest? Reinvent fastest.

The AI Squeeze Is Accelerating Everything

AI isn’t replacing people. It’s replacing the middle layer most careers used to grow through.

Marketing analyst? Your CEO now does it with ChatGPT.
Copywriter? Midjourney and Gemini 6 can draft a whole campaign in seconds.
Junior strategist? AI automates 60% of the job.
Data entry? Gone.
Content coordinator? Shrinking rapidly.
Presentation building? Nearly automated end-to-end.

The “learning years” have evaporated.

Which means the question isn’t: “How do I protect my job?”
It’s: “How do I build a career AI cannot replace?”

And the answer is simple:

Become the human who directs AI, not the human AI was designed to replace.

AI can write, research, design, and synthesize.

But AI cannot replicate:

• Sensemaking

• Storytelling

• Discernment

• Emotional intelligence

• Leadership

• Taste

• Courage

• Vision

And that’s because everything listed above requires you to have something at stake. AI has no skin in the game, so it can’t distinguish between outcomes that matter and outcomes that merely satisfy the prompt.

That is your edge. That is where reinvention begins.

The Layoff Wave Isn’t About You, It’s the System

Recent layoffs aren’t performance-based. They’re structural.

Economic Policy Institute (2025) and BLS data show:

• 2025 layoffs concentrated in middle-management and “coordination” roles.

• Companies restructuring for AI efficiency cut entire functions, not individuals.

Companies are responding to:

• AI efficiency

• cost reductions

• margin pressure

• private equity restructuring

• consolidation

• the collapse of middle management

• remote work reorganizations

• global competitiveness

Departments are disappearing overnight, not because humans weren’t performing, but because machines made the work cheaper and faster.

Every organization that collapses does so because it has become more interested in protecting what it has built than in building what comes next.

You didn’t fail. The role failed. The systems failed. And now you get to choose what you build next.

The Portfolio Career Era Has Arrived

If the old dream was stability, the new dream is sovereignty.

A portfolio career = multiple identities + multiple streams + multiple customers.

You stop being an employee. You start being an economy. This isn’t a trend, it’s a structural reset.

2026 labor trends show:

• Fractional executive roles up 40% year-over-year (Brex Talent Insights).

• Solopreneurs driving nearly $2 trillion in U.S. economic value (IRS/BEA, 2024).

• Over 50% of Gen Z prefer self-employment (Bankrate Gen Z survey, 2025).

The safest career today is the one you control, not the one a company can end in a single email or zoom call.

What My Layoff Taught Me About Reinvention

When I lost my job, I had to face something painful:

I had built a career.
But not a platform.
Not a community.
Not an identity outside the machine I served.

A company can take your job.
But it cannot take your voice.

For me, one layoff created multiple new lanes: building The Next Billion Dollar Brand, launching This Is Not A Memo on Subtack, doing consulting work, writing my book, booking keynotes, working at Marvel Studios at Disney (a childhood dream), and building a whole new community from my personal brand.

That’s what reinvention looks like: expansion.

My 5 year old daughter told me this week she wants to be a science teacher, a fashion designer, a CEO, and a veterinarian. The baby boomers would have told us to pick one lane, the most stable option.

I told her: “Be all of them, as long as you work hard, are passionate, and focused, anything is possible.”

That’s the same answer I would tell a 40 year old who’s going through a second or third act in life, and looking to reinvent themselves. And it’s the same advice I give myself.

The 7 Reinvention Plays for the AI Job Squeeze (Bubble-Proof Edition)

Your blueprint for 2026 and beyond.