The holidays create a rare pocket of space—enough quiet to sit with an idea a little longer than usual, or to let a story unfold without interruption. If you’re looking for something to read and something to listen to that reward attention, these two have been sitting with me.
This book (part of Taleb’s broader Incerto series, though it stands well on its own) has deeply shaped how I think about shared risk—between myself, my teammates, and the customers we build for.
At its core, Skin in the Game is about alignment:
Who bears the cost of decisions?
Who absorbs the downside when things go wrong?
And who quietly walks away untouched?
Taleb pulls from everywhere—ancient philosophy, probability, religion, and business—to argue that systems only work when those who make decisions are exposed to their consequences. It’s wide-ranging, sometimes abrasive, often funny, and consistently clarifying.
One quote that captures the book’s spirit:
“The curse of modernity is that we are increasingly populated by a class of people who are better at explaining than understanding, or better at explaining than doing.”
I return to this idea often when thinking about leadership, incentives, and what kind of organizations are actually worth building over the long run.
It’s rare for an album to feel like a novel—one that carries you from beginning to end, leaves you changed, and doesn’t ask to be shuffled or skimmed.
This one does that.
The Ballad of Dood & Juanita tells a quiet, tragic, beautiful story set against the western frontier. Love, loss, loyalty, violence—nothing wasted, nothing rushed. When it ends, it feels like you just closed the back cover of a great book.
One rule if you decide to give yourself this gift:
Listen to it straight through.
In the quiet.
Maybe with a fire going.
Maybe with a drink in hand.
Some things are better when we let them take their time.
***If you end up reading or listening to either, I’d love to hear what sticks with you. The best recommendations tend to compound when shared.
