“Don’t confuse stability with security. The most stable job might be the least secure in a changing world.”
— Dan Koe
A few months ago, if you had asked me what a “portfolio career” was, I probably would have assumed it had something to do with investment banking.
In case you’re wondering, I recently came across a LinkedIn article that describes a portfolio career as …
”choosing paths that align with your strengths and complement one another. It builds flexibility, sharpens your skills, and provides security in changing markets.”
When I read this, I immediately recognized myself in it, as if I was getting a real-time reflection about the state of my work and the path I’ve been traveling.
But I didn’t plan for it. I didn’t read a book or take a course or map out a five-year plan.
I created it, almost by accident.
The Unravelling
Like many of you reading this, I spent years in the corporate system. I had the title, the salary, the calendar full of “important meetings.” I was succeeding in every conventional sense of the word.
But quietly, something felt off. I wasn’t quite burned out. But I was bored. Disconnected. Boxed in by a role that no longer felt like a soulful fit.
There’s a quote I love (often attributed to Joseph Campbell):
“If the path before you is clear, you’re probably on someone else’s.”
That was me.
The more I followed the script, the more I felt like I was living someone else’s life.
And then, one small experiment led to another.
The turning point: Designing around alignment instead of status
My first taste of alignment came from coaching a few people on the side – for free.
Nothing fancy. Just sharing what I knew about intentional careers, seeking autonomy, validating ideas, and the quest for more meaningful work.
It wasn’t a side hustle. It wasn’t a business plan. It was a way to feel connected to something personal again.
But that small act cracked something open. I started seeing a new glimmer and questioning the default path.
What if work could be built around my life instead of the other way around?
What if I could have more personal meaning?
What if I could do multiple things I enjoy instead of trying to force all of me into a single role?
That’s how my portfolio career began to take shape:
- A bit of coaching
- A workshop here, a keynote there
- A few consulting engagements
- A podcast
- A fractional leadership development role
No grand plan. Just intentional interest and skill stacking.
What I discovered: Portfolio careers aren’t a trend – they’re the future
The world is changing fast. Layoffs, AI, remote work, shifting values. The traditional career ladder is wobbly at best.
In that context, a portfolio career isn’t just a clever alternative – it’s a strategic advantage in a changing system.
It allows for flexibility.
It reduces risk by diversifying income.
It gives you room to experiment, to evolve, to grow.
And most importantly, it lets your work reflect your life.
The 5 key lessons I’d offer anyone exploring this path:
- Start with what you know and who you enjoy helping
Don’t reinvent yourself from scratch. Identify the skills you’d take with you. In my sales executive role, I had developed the skill of coaching others through decision making. I also developed the skills of teaching and facilitating at large tech conferences. And finally, I had developed the skill of building and nurturing key connections. - Think in terms of experiments, not exits
You don’t need to quit your job tomorrow. Start something small and see how it feels. I coached on the side for almost two years – for free at first and then for a fee. I started saving a portion of my paycheck and almost all of my coaching income was set aside in a ‘freedom fund’ to help smooth the transition if and when I decided to leave my primary career. - Design for energy vs. chasing trends
Choose to experiment with ideas that are interesting and energize you. The more you engage with your own interests, the more your ideas compound and become unique through the lens of your personal experience. Sure, AI is trendy. But if it doesn’t interest you personally, it’s probably not a sustainable path. - Time is your real currency
Before you optimize for income, optimize for how you want to spend your hours. This is the foundation of what I’m starting to call The New Wealth – designing a life around what matters: Autonomy + Creativity + Meaningful Work + Living Intentionally. - Don’t go it alone
Surround yourself with others who are walking a similar path. Collaborate on projects with people who share similar values. Nurture relationships that could be useful in the future, without any expectation of reparation.
Final thought: The Future of Work
I didn’t set out to build a portfolio career. I set out to feel more alive.
What I stumbled into was a model that supports creativity, interests, income, and flexibility – on my terms.
Today’s environment no longer requires you to choose one identity. In fact, sticking to a single lane might limit your potential. Start small, build gradually, and remember your career can be as multidimensional as you are.
And if you’re feeling that same itch, that quiet discontent, you’re not crazy – you’re just waking up!
Live bravely,
Michael
