Where one career ends and many begin
For many of us who started our careers 15 or 20 years ago, the image of success was clear. Get a good degree, join a reputable company, climb the ladder, stay long enough to reach the top — or at least somewhere close. We knew times were changing, but we still expected a sense of continuity. A linear path, or sort of it. A ladder to climb.
That world doesn’t exist anymore — and that truth is both liberating and unsettling. Job security has become an illusion. Economic crises, pandemics, AI, and the constant cycle of “restructuring” have reshaped the workplace.
Even great employees get let go. I’ve been there too. And while I didn’t yet have a family back then, I can only imagine the added weight when others depend on you. The reality is: relying on one source of income has become the riskier choice.
The world of work has changed — hybrid setups, remote teams, freelancers, consultants, creators. But more importantly, we have changed. Our values, our priorities, our definitions of success — and none of them are the same as when we started.
For many high achievers, careers once defined us. They shaped our identity and self-worth. Now, that identity is shifting. We are no longer who we used to be, yet not quite someone new. The old no longer fits — but the new still feels far away.
I like to call it the “messy middle.” The in-between where we sense change coming but don’t yet know what it looks like. It’s where the old identity fades before the new one fully form, and where much of the real transformation happens.
One of the biggest emotional shifts I saw in myself, and my clients, happens when we move from belonging to a company, brand, or job title, to belonging to ourselves.
For many high-achieving, ambitious women, this feels like uncharted territory. They’ve defined themselves through achievement recognition for so long that even considering leaving can feel like failure.
But the real work of transition isn’t logistical, it’s emotional. It’s about identity, belonging, and letting go.
It starts with asking:
Who am I today?
What does a career that fits this version of me look like?
What could I create if I designed work around my life, not the other way around?
That’s where the idea of a portfolio career comes into a career made up of several complementary roles or projects, built around who we are and what matters to us.
In a portfolio career, we:
Disassociate our identity from a single job or title
Leverage different parts of our experience and expertise
Enjoy variety, flexibility, and creative freedom
Adjust our work to different seasons of life
Design careers that reflect the lives we want — not ones we have to fit into
Portfolio careers can bring choice, balance, and ownership. They let us double down on our strengths rather than patch up our weaknesses. They make change and non-linear path - normal.
Because at the heart of it, a portfolio career isn’t just a professional model. It’s a mindset. One that acknowledges that we evolve — and that our careers should be evolving with us.
We do not always choose when one chapter ends, but we can choose how the next one begins.