Essay · Jan 2026
The portfolio career, defended
Sabrina Depestre made a point on episode 25 that deserves its own piece. Side projects are not a distraction. They are the engine.
I’m a CEO and a painter. For a long time I felt I had to apologize for that, as if the painting were an indulgence, the day job the real thing, and never the twain should meet.
They meet constantly. The painting trains my eye. The eye makes me a better strategist. The strategy pays for the paint. The paint reminds me why the strategy matters.
You don’t have a main thing and side things. You have a practice, and several surfaces it shows up on.
