The II Ladder

Three months ago, I watched a friend with 10+ years at the same company get laid off over Zoom.

It seemed to me so unjust. And it got me obsessed with the concept of career security, independence and financial stability in the new economy.

In today’s essay you’ll learn:

• a realistic look at career security in 2025

• which trends I’m watching in the labour market

• why I’d bet on the independent income ladder > the career ladder

If you see a part of this essay you love, screenshot it and share it on Linkedin. If you tag me and Generalist World I’ll help amplify it to our network of 40,000+ new-traditional professionals.

Thanks for being here!

Milly

Professional “security” is BS

The word “professional” stems from “profess”—a public declaration of specialty. For decades, we were told this was the path to security: specialize, earn the right credentials, stay the course, and you’d be rewarded with stability.

That promise has unraveled.

The stability that traditional employment offered was always conditional, subject to economic shifts, technological disruption, and the whims of distant decision-makers.

Today's job market is saying the quiet part out loud. A full-time job isn’t necessarily secure. Traditional work isn’t necessarily stable.

Companies that seemed unassailable a decade aren’t necessarily bulletproof. Entire industries aren’t necessarily going to be the same when you wake up tomorrow. And so betting everything on a single skill set, a single employer, or a single industry is risky.

I’ve found that the real path to security isn't doubling down on specialization—it's leaning into (financial, time, life) independence.

Ecosystems > Assembly Lines

Instead of thinking about careers as declarations of specialty, I’ve found it useful to think about them as ecosystems.

And my favourite example of an ecosystem? My garden.

You can't plant a field of only potatoes and then be shocked when potato blight wipes out your entire harvest. That's monocropping—the agricultural equivalent of overspecialization—and it's incredibly vulnerable.

No—you succeed by understanding how different elements interact, knowing how seasons change, and understanding how to cultivate multiple plants that complement each other.

This ecosystem approach is why the most interesting careers today look more like gardens than assembly lines.

Take someone like my friend, Jeanine Suah. She’s a Founder, XIR, Linguist, and Community Growth Expert. Jeanine is a 🔥 example of someone who’s cultivated her garden over many years; building relationships, influence, reputation and skills along the way.

Or Wes Kao. She’s a coach, founder, writer, speaker and marketer. She seeded her garden with marketing expertise, and has now branched out into teaching leadership and effective company building. During her Generalist World masterclass, she opened with “I’m a proud generalist”. It was a moment! 💡 

Or Neda Sahebelm. If you need to learn about quality scaling, you go to Neda. But she got here by being an IO psychologist, a COO, a speaker, and an angel investor. You’ll often find Neda speaking on panels not because she’s followed a straight line, but because, in her own words, “having done it long enough, failed enough and learned enough to turn mistakes into hindsight, lessons and playbooks”

Introducing the II Ladder: a new model for careers

For decades, we've had one dominant mental model for career advancement: the Career Ladder. It's vertical, linear, and singular. You start at the bottom and climb steadily upward, collecting titles, responsibilities, and (hopefully) bigger paychecks along the way.

But this model no longer reflects how value is created or how meaningful work happens in today's economy. We need a new mental model—what I call the "II Ladder" or Independent Income Ladder.

The Five Pillars of the II Ladder

This is the juice—the core of what makes the II Ladder so powerful in today's economy:

• Horizontal Growth
  Traditional path: Becoming the expert in one narrow field.
  II Ladder: Developing complementary skills that create unique combinations others (and technology) can't easily replicate. The marketer who codes. The designer who writes. The lawyer who understands UX.

• Income Portfolio
  Traditional path: One job, one income stream, one point of failure.
  II Ladder: 3-5 complementary income sources that balance stability and opportunity. When one stream dips, others can compensate.

• Ownership
  Traditional path: Trading time for money, building someone else's equity.
  II Ladder: Creating assets you own—digital products, content, equity stakes, royalties—that generate returns long after the initial work.

• Value-Based Compensation
  Traditional path: Getting paid for showing up 40 hours weekly regardless of impact.
  II Ladder: Structuring work where compensation scales directly with the value you create. The more impact, the more upside.

• Network Power
  Traditional path: Deriving status and security from your position in a hierarchy.
  II Ladder: Building an ecosystem of relationships across industries and domains that creates resilience

This shift reflects a fundamental truth: innovation, compound trust, and value creation happen most effectively when workers have the freedom and frameworks to design their work-life.

Smart companies are also fast recognising this new reality. The CEO of Gamma, Mr. Lee, says:

What’s in your portfolio of value?

Poly-employment—holding multiple jobs—has surged to 5.19% of the U.S. workforce, the highest rate since 2009. Another way of thinking about having multiple jobs is through the lens of a portfolio of value.

Your portfolio of value might include:

• Consulting work

• Digital assets

• Content or code

• Equity or profit-sharing in ventures you contribute to

• Income from angel investments

• Fractional roles

• Speaking fees

These elements don’t exist on their own either. They form your career flywheel.

Each stream might start small, but together they create a foundation far more stable than any single job. When one stream diminishes, others can compensate. When opportunities arise, you can redirect energy without risking your entire livelihood. This is a fundamentally new way to create value.

(I talk more about the value generalists create in this essay: the generalist value pyramid).

Independence as freedom

The part of the II Ladder I get most jazzed about is independence. Independence means freedom to choose how you live, work, and build. Whatever happens in life—becoming a parent, supporting a partner, helping family members, pursuing personal passions—work can blend in rather than demanding rigid separation.

Independence is freedom, and freedom is why we're here. The II Ladder doesn't just offer a path to financial security; it offers a way to design a life that reflects your values and priorities.

When you climb the II Ladder, you're not just seeking higher income—you're seeking the autonomy. You gain the flexibility to close your laptop at 3pm to go camping with your kids, without asking anyone's permission. That is what I’m here for.

By 2027, half of America's workforce is projected to be independent and the creator economy is approaching $500 billion. So what does this mean?

First we had industrial era.

Then we had professional era.

Then we had the gig era.

Then we had this weird period where the new-traditional was emerging, but the old-traditional still dominated. People who thrive in this era felt out of place and like they didn’t quite belong anywhere.

It’s inevitable.

By 2030, multiple income streams will represent less a choice and more a structural inevitability. The number of independents making more than $100,000 annually rose in 2024 to 4.7 million – that’s up sharply from 3 million in 2020. Many of these will be independent workers.

The II Ladder isn't just a new way to work; it's a new way to live. It acknowledges that our value can't be contained in a box, that our contributions are richer and more meaningful when they reflect the full breadth of who we are.

My big questions lay in not whether most people will have multiple income streams, but how fast society will adapt to sustain this new economy.

After all, we survived as a species precisely because we could combine multiple types of knowledge. Now, we just have the opportunity to bring this to how we work.

Your First Steps Toward Independence

If you're intrigued by the II Ladder approach but not sure where to start, here are three simple ways to begin:

1. Plant your first seed: Dedicate just 2 hours per week to exploring one new potential income stream. What skill do people already ask you for help with? Could you package that knowledge?

2. Find your companion plants: Identify 2-3 areas where your existing expertise could be valuable in adjacent fields. If you're a marketer, could you advise startups? If you're a designer, could you create templates?

3. Start harvesting: Look for ways to create assets from work you're already doing. Could that internal training you developed become a workshop? Could that spreadsheet you built become a template others would pay for?

The beauty of the II Ladder is that you don't have to (and in fact, I strongly recommend not) quitting your job tomorrow. You can start small, planting seeds while maintaining your primary income, then gradually shift as your garden grows.

Jumping-off questions:

Things you might like to reflect on, or share on LinkedIn (tag me!)

• Would you rather have: a) one job paying $100K or b) four income streams adding up to $120K? Why?

• If you spent 2 hours a week building a second income stream, how might your life be different in one year? What would that stream be?

• What part of traditional employment feels most restrictive to you? How would independence change that?

• What part of your current work feels most aligned with who you really are? What part feels least aligned?

• What does ‘wealth’ really mean to you?