Charlie Munger, Warren Buffett’s right hand man, had a strange habit. Whenever he made a big decision, he’d ask himself a simple question:

“How could I fail?”

Over the years he built a list of failure traps: ego, envy, inconsistency, laziness, and self-deception. His rule was brutally practical: “Just avoid these and you’re ahead of 90% of people.”

But one of his beliefs has stuck in my head as we head into a new year.
Munger thought “playing it cool” was a trap.

He believed in asking questions.
In not pretending he knew everything.
In staying visibly curious.
In refusing to shrink just to look composed.

“I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up and boy does that help, particularly when you have a long run ahead of you.” -Munger

The opportunity cost of playing it cool is that you miss out on learning from the people you admire.

As I’ve gotten older, I’ve learned one of my biggest weaknesses is playing it cool.

Two weeks ago I sat down with a man who owns a 150-person company. I made some jokes, kept the conversation casual. I think he liked me.

But I don’t have a clue how he built his business. Or what he might have done differently. I don’t know, for example, what advice he might have for a person who’s just starting out on their own. Someone like me.

I, like many, tell myself I’m being respectful. Or professional. Or low-maintenance.

But Munger would tell a different story. I’m being performative in a way that leads to missed opportunities.

And the part that bothers me is this: those missed opportunities don’t disappear; they compound.
A question you don’t ask becomes a relationship that never deepens.
Do that often enough and one day you wake up surrounded by people who like you… but can’t really help you become who you’re trying to be.

So in 2026, maybe it’s time to be done pretending.

Because when I think about the people who’ve moved me most, the ones I remember, their defining trait usually isn’t coolness. It’s presence. They laughed too hard. They asked questions that made me think. They admitted when something mattered to them.

They were alive in the room.

“The fear of being embarrassed is a very powerful force.” — Charlie Munger, from a talk in 1995.

The window shades are drawn down
How many sunrises does one get in a lifetime?
27,000 if they’re looking.
How many few
if they live like you
and draw their shades down.

Until next time,

Live your light.