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Consider A Portfolio Career

Exactly three years ago, I was designing Halsey’s Manic World Tour staircase.

Today I’m working on vastly different projects. It wasn’t starting over, I had new skills (and a lot of knowledge on how concerts work).

I’m not the only one with these career transitions. Look at the Great Resignation: over 4 million Americans quit every month for a year. Employees that switched jobs in the last two years often haven’t met a single coworker in person. And there are more coworking or hybrid workspaces than ever.

Modern work is changing.

Our society has both the language and the infrastructure to create more dynamic work experiences. Enter: the portfolio career as a way to think about and craft a professional future.

A portfolio career is a process of discovery and fulfillment, trials and failures. It is a journey. The work reflects an evolving identity and an innate desire to learn.

For example, some titles in my portfolio include researcher, project manager, writer, speaker, designer, operator, and investor.

Portfolio careers are gaining traction.

Rich Roll recently commented, with a twinge of personal regret, on the benefits of a diverse career. “You become a more robust individual. You understand different walks of life and different perspectives. You start to figure out what you enjoy doing and what you don’t enjoy doing.”


“Let fools rush in where angels fear to tread.”

The famous Henry Ford believed strongly in experimentation.

He was such a believer in the power of experimentation and the benefits of failure, in fact, that no one in the factory could keep a record of the factory experiments that were attempted and failed. Keep those records and “you will shortly have a list showing that there is nothing left for you to try.”

How does this relate?

Experimentation is the keystone of a portfolio career. Intentional experimentation adds to a tool belt of experiences, but it’s important to connect the dots or the journey can be ambiguous.

To navigate that ambiguity, look at another familiar portfolio. An investment portfolio is constructed to diversify holdings and mitigate risk. A portfolio career requires the same: diversifying the types of work to create a balanced career portfolio and allow yourself the opportunity for upside. “Sprinkle in the $10k (high-leverage work) pixie dust,” as RadReads’ Khe Hy would say.

Like structuring an investment portfolio for retirement savings, building a career portfolio is the equivalent of crafting a professional future. For me personally, framing the future as a portfolio career has helped to turn what might appear as dots into insights.


Specific experiences or skills might offer just the impact that someone needs down the road. And companies today value employees with a set of unique and diverse experiences. For me, applying a systems-thinking mindset that I learned as an engineer to non-engineering work has been rewarding as I can create no-code operations and repeatable business operations.

It can be a struggle, though. For all the strengths that portfolio thinking offers, there is less security available and it often requires more energy. You have to draw the career map instead of reading it, and while that’s a valuable skill, not every potential employer or field will embrace that style.

But at the end of the day, building a diverse set of experiences keeps us learning. To close with another Ford quote, “The moment one gets into the ‘expert’ state of mind a great number of things become impossible.”

Stay curious.




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