💡 The OG Portfolio Careerist

In December 2024, as portfolio careers started to shape public workplace discourse, Charles Handy, who coined the term 35 years prior, passed away at 92. This was fitting symmetry: the visionary departed just as his radical ideas from his seminal work The Age of Unreason (1989) finally became more mainstream.

His death marked both an ending and a culmination, the moment his once-radical blueprint for work became… orthodoxy?

Something about the way the online discourse was evolving toward "polywork" created unease within me, though. The portfolio career Handy envisioned was a deliberate rejection of the corporate identities that defined industrial capitalism.

Before you dismiss this as academic theory, consider that Handy's philosophy emerged from his own crisis of purpose. His ideas were forged when he deliberately walked away from a successful 17-year career at Shell Corporation to build a life beyond corporate confines (link to my essay on the life and legacy of Charles Handy further down below if you care to read it!). Everything he subsequently wrote—his vision of work-life integration, his rejection of industrial capitalism's logic—was shaped by this personal journey from disillusionment, to.. hope.

His life became the laboratory for the revolutionary ideas that followed.

So what did a portfolio life mean to Handy?

1. Work structured around your values

2. Income streams that complemented each other

3. Skills that transfer and compound across different domains

4. Time allocated intentionally with boundaries that honor rest

5. Identity rooted in purpose rather than professional titles

Pretty radical way of looking at life for a white dude that spent a big portion of his career in the oil industry, right? Especially considering he saw the world this way over thirty years ago. He was kind of an enigma!

Anywho… THIS is the portfolio career philosophy that I personally am drawn to. And it forms the backbone of my coaching practice and my own portfolio career.

But lately, I feel us resisting parts of this model—not because we disagree with it, but possibly because the ground beneath us feels too unstable to trust it.

More and more, I see professionals—especially those who’ve been out of work for prolonged periods of time—promoting portfolio careers through a fundamentally different lens. In the last few months in particular, it’s becoming a tool of financial survival in the face of institutional collapse.

And here's the tension I can’t shake: The very philosophy designed to create integration is now being framed around optionality. Spun as freedom, but smells like… fear?

That growing disconnect became crystal clear to me last week—reading a Guardian piece on the rise of polywork among millennials, followed by Elena Verna’s blog reflections on the future of full-time work after leaving Dropbox.

It has me wondering: Are we trading intention for survival strategy? And self-authorship for self-optimization?

The question isn’t if—It’s which.

The technological infrastructure Handy could only imagine finally exists. Remote collaboration. Asynchronous work. Community-led models. These tools make his vision possible on a global scale!

Yet instead of embracing this moment with intention, we seem to be diluting Handy’s philosophy: work lives driven by anxiety rather than purpose.

And in that desperation, I believe that we risk building something brittle in it’s place.

Now before you roll your eyes, know that I'm not arguing against polywork. We all need to be able to provide for ourselves and our families. To put food on the table.

The point that I am making is that I believe there's a profound difference between fragmented work born of precarity and an integrated portfolio life designed as an expression of your fullest self.

Handy’s vision was about imagining possibility in the face of disillusionment. About creating work that honors ALL dimensions of who you are as a radical act of creative expression.

The true power, then, of this philosophy then isn't that it’s ability to shields us from uncertainty, but it’s ability to empower us to build something authentic in spite of it.

And perhaps that's the most fitting tribute we could offer to Handy's incredible legacy.

Because portfolio careers are the future of work. There are no questions about that.

The real question is: which version of the model will we choose?

One born from economic fear and institutional failure?
Or one rooted in humanity, agency, coherence, and purpose?

If you want to learn more about Handy’s life, I go deeper in the second essay of my portfolio career series.

You can read it —> here