Skin in the Game

The Hotpot | March 2026 | By Lisanne

26.3

When do we actually become an expert?

Is it after ten years in the workplace? When we get that one title? Or simply when we decide it ourselves?

Nassim Nicholas Taleb is quite matter-of-fact about it in his book Skin in the Game:

“Knowledge without skin in the game is like a map without a landscape—useless and dangerous. If you don’t take a risk, you don’t truly understand the machine you are operating.”

As he famously puts it:

“Don’t tell me what you think, tell me what you have in your portfolio.”

Source: Skin in the Game by Nassim Taleb.

If we follow Taleb’s logic, the ‘expert’ isn’t the one with the most answers, but the one who has collected the most experiences.

For Taleb, reality is a merciless teacher; it corrects the “doer” immediately, while the theorist remains safely on the sidelines. When we have skin in the game, the feedback from reality is our true teacher. It can help us collect evidence of the things that worked out.

It’s true we trust the pilot more than the flight simulator designer, and the entrepreneur more than the consultant. The practitioner’s knowledge is literal—it is etched into their reality through the “cost” of their mistakes. They have stepped into the arena, let the world respond to their theories, and ultimately learned by doing based on that feedback.

It’s interesting how, when the world responds to what we ship, it is correcting our trajectory with the weight of consequence. We become experts not when we master the theory, but when we have something to lose.

Ironically, most of what we call expertise in the modern world is actually asymmetrical: the theorist enjoys the upside of being right (think of prestige, citations, tenure) while someone else bears the downside of being wrong.

So what if the ‘title’ isn’t what makes us an expert, but the liability we are willing to accept?

Perhaps the most provocative question we can ask a self-proclaimed expert isn’t “What do you know?” but rather, “What is the most expensive mistake you’ve ever made, and why are you the one who can ensure it doesn’t happen again?”

Thank you for reading! The question of today:

What is the most expensive mistake you’ve ever made, and why won’t you make it again?