DAVINCI: THE OG PORTFOLIO CAREERIST
Why “portfolio work” might be our most natural—and necessary—way to earn a living.
Last week in Florence, I wandered into the Da Vinci Museum—an interactive shrine to everything Leonardo touched:
Art
Engineering
Military inventions
Medical models
Mathematics
The breadth is staggering. I laughed imagining someone telling him to “niche down” and focus on one thing.
Truth: Leonardo never had a “job” as we think of it. He had patrons, essentially clients.
Apprentice to Andrea del Verrocchio
Worked for Duke Ludovico Sforza as painter & engineer
Advised Cesare Borgia as military architect
Later, King Francis I of France granted him a stipend, villa, and title
Portfolio work isn’t new. It was survival.
WHEN DID CAREERS GET SO NARROW?
Historically, work was plural:
Farmers brewed
Blacksmiths forged and repaired
People shifted trades with the seasons
Then came the Industrial Revolution: factories demanded specialisation, predictability, efficiency. Education followed suit. Work became a box. Stability became obedience. Curiosity became a liability.
CURIOSITY IS THE POINT, NOT THE PROBLEM
A supervisor once warned me, “Getting bored easily will be your downfall.”
Reality check: curiosity lights up the brain, spikes dopamine, improves learning, and makes humans sharper.
Monotony dulls
Variety enhances
Curiosity drives human engagement
Humans aren’t designed for narrow repetition—they’re designed for exploration. If you feel restless in a single lane, that’s wiring, not weakness.
THE TAKEAWAY
A portfolio career isn’t easier. It requires more operational thinking than a traditional 9-5.
But the payoff? Sovereignty.
Humans have historically earned through range, adaptability, and curiosity
Industrial-age single-employer careers are an anomaly
Technology, remote work, and personal agency are swinging the pendulum back
Practical steps:
Audit your skills – What do people already come to you for? What comes easily to you that’s hard for others?
Define a few lanes – Two or three is plenty (consulting, writing, teaching, design). Keep it interesting, not scattered.
Package it for purchase – Define outcome, timeline, and price. Answer: “What does it look like to work with you?”
Start publishing proof – Share insights, write, teach, show your work. Every post is a breadcrumb for the right people.
Build income insurance – Visibility + credibility = livelihood security
Your career is a living portfolio: try new things, retire old ones, adjust as you go. Security comes from adaptability and curiosity, not a job title.
Lesson from Leonardo:
He didn’t have a job. He had a body of work. Reputation, range, and experimentation were his insurance policy. You can do the same.
QUESTION
Q: Hesitant to hire after a rough few years? What if the economy dips?
A: Build flexibility into your rebuild:
Start with part-time roles with elasticity
Focus on skill and mindset, not just hours
Be transparent about business status and potential growth
Transparency attracts adults who value honesty, agency, and flexibility. Start part-time, define scope, scale intentionally.
WORK WITH ME
Keep building the version of work that actually works for you. I’ll be here cheering (and occasionally nudging).
