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DaVinci: the OG Portfolio Careerist
Why “portfolio work” might be our most natural—and necessary—way to earn a living
Mary Alice Duff
November 03, 2025
Hey reader,
I’ve just returned from ten days zipping around France and Italy. I worked from a teeny-tiny hotel room in Paris, coaching a group of fractional ops folks. I built next year’s budget for a deep-tech client (as their fractional COO) while riding the train between Milan and Florence. And I wrote the essay below from an olive grove in Tuscany.
In short: I’m living a portfolio career—meaning I earn money in a few different ways, flexing across projects, clients, and skills. And I do it completely remotley. I like it. It lights my brain up. Keeps things interesting. It taps into my relentless curiosity, which means I never get bored—and that’s just how I like it.
Today’s long read was inspired by a stop at the Da Vinci Museum in Florence. Hope you enjoy it.
Onward,
Mary Alice
Table of Contents
DaVinci: the OG Portfolio Careerist
Why “portfolio work” might be our most natural—and necessary—way to earn a living
I spent last week in Florence and wandered into the Da Vinci Museum—an interactive shrine to everything Leonardo ever touched. Art, engineering, military-grade weapons, medical models, mathematical concepts—the sheer breadth of his work is staggering.
As I moved through the exhibits, pausing in front of replicas of The Last Supper and sketches from his personal notebooks, then spinning gears on his flying machines, I couldn’t help but laugh. Can you imagine someone tapping him on the shoulder and saying, “Leonardo, this art stuff? It’s great and all. The Mona Lisa? Exquisite. But maybe cool it with the frescos and niche down. Focus on the military-grade scuba suit or that ladder contraption for scaling city walls.”
That thought stopped me mid-gallery. Because while we love to romanticize genius, we rarely ask the practical question: how did he actually make a living doing all of that?
And maybe more importantly: was that normal?
And if it was—when did work get so damn narrow?