Mailbox Mutterings with Charlie
Our stories, protecting the herd, and the value of being wrong
My Grandpa’s name was Charlie. He died when I was young but lived on in family stories. He worked for the Minneapolis Gas Company for more than forty years, rising from laborer to union president, and took pride in being a servant leader. When I was born, my parents were at the hospital, and my Dad mentioned to his Mom on the phone one evening that he was stuck in sweaty socks. Around midnight, Charlie drove across town to deliver a clean pair.
Years later, we named our family dog Charlie. He was small, oddly indestructible, and like most dogs, offered unconditional love. When it came time to put him down, my normally stoic Dad said it was one of the hardest things he’d ever done. For months afterward, Charlie’s yellow leash sat in the back window of his car.
Later on, I stumbled upon a book called Poor Charlie’s Almanack. The title alone made me pick it up. It’s a collection of Charlie Munger’s talks on decision-making and human behavior. One idea stuck: bad outcomes often stem from flawed thinking, not bad intentions.
After reading it, I found myself trying to work his lines into everyday conversation. I imagine Charlie as the elderly neighbor you pass at the mailbox, muttering something that leaves you thinking for days, and I’ll borrow him as my guide.
About halfway through my entrepreneurial journey, I was serving on a board that used a behavioral survey to better understand how we showed up as individuals and as a team. What made it compelling was its focus on natural tendencies — patterns shaped by genetics, early environment, and years of reinforcement that tend to remain fairly stable once we reach adulthood.
We met virtually to review the results. One of the first slides listed each member’s name alongside a snapshot of their dominant behaviors. When I saw mine, a few themes jumped out. A need for control. Impatience for results. A tendency to push harder when challenged. I wanted to disappear from the call.
It wasn’t that the labels were wrong. It was the first time they had been named publicly, with an objectivity that made them hard to dismiss. Some might say these behaviors fit a business leader or entrepreneur. But they didn’t fit the way I wanted to show up. I noticed the words attached to others. Collaborative. Steady. Adaptable. I admired them. I could feel the heat rising as my mind went straight to justification.
My first mailbox conversation with Charlie went like this.
Me: These behaviors are what made me successful. They get results. Letting go of them feels risky. They are hard-wired, not chosen.
Charlie: That may be. But above all, never fool yourself, and you are the easiest one to fool.
My reaction to those labels comes from a part of the brain built for protection, not reflection. It scans for threats and pushes us toward speed and certainty, an encoding shaped for prehistoric dangers that no longer apply.
If it had a big brother, it would be ego.
Ego arrives next, tasked with defending, justifying, and creating a story that makes it feel reasonable, even necessary.
When this loop takes hold, the body reacts. Heat rises. Breathing shortens. Vision narrows. Urgency starts to feel like clarity. Justification follows with certainty.
And once the story has been told, the system is primed to defend it against the next time it’s challenged. Even if part of you suspects it isn’t true, the instinct is to double down.
In a calmer, more rational state, I could see that these labels were not how I wanted to be experienced, and that change mattered. I could still drive results, but with softer edges, knowing it would take work to unwind some of those tendencies.
Once I became familiar with the threat–ego–story pattern, it started showing up everywhere.
I’ve coached youth hockey for nearly a decade and have watched the same sequence play out hundreds of times. A slash to the wrists. An instant slash back. Then comes the argument with the referee on the way to the penalty box, followed by the explanation to the coach. He deserved it.
A friend of mine, a role model for young women, was challenged on why she wasn’t coaching her daughter’s soccer team. Her answer came without hesitation. I don’t have the patience to manage a large group of six-year-olds. This from an elite athlete, successful entrepreneur, and published author.
I watched an executive publicly challenged over a failed software integration that cost stakeholders hundreds of thousands of dollars. When pressed to bring in an outside auditor to better support future integrations, he pushed back. His team, the same one that had overseen the failure, had already investigated and identified the root cause. We understand what went wrong. There’s no need to bring anyone else in.
Different situations. Same response. A perceived threat. Ego steps in. The story follows. And once it does, you feel the need to defend it. Something harder goes unexamined.
I started to see how this pattern extends beyond defending ourselves and into the belief systems we adopt. Author Morgan Housel says it well:
The best definition of independent thinking is when your beliefs on one topic can’t be predicted from your beliefs on another topic. If you tell me what political party you belong to and I can instantly and accurately guess your views on immigration, abortion, taxes, and guns, are you really thinking independently, or just going along with your tribe?
Few things trigger our defenses faster than being told we’re not thinking for ourselves. But it’s worth asking how much of what we believe is truly ours. How much did we absorb from our parents and communities? How much continues to be shaped by the environments we move through? At some point, the more useful question is what have we actually examined — and what are we simply running on autopilot?
At the next mailbox meeting with Charlie.
Me: I’m starting to wonder how much of what I believe I arrived at on my own, and how much simply came from the environments I’ve lived in.
Charlie: That’s human nature. Just remember, if you follow the herd, you tend to regress to the mean.
It hit closer to home than I expected.
As a Minnesotan, I live in an area that recently became the focus of a large federal immigration enforcement effort, sparking protests, lawsuits, and intense political debate. Two local residents were killed in the events that followed.
As my wife and I prepared for a family conversation and the questions our kids would inevitably ask, it became clear how little we had actually thought through the topic of immigration. We wanted to be ready, but the more we looked, the less certain we felt.
The issue revealed how law, economics, border security, humanitarian responsibility, and the realities faced by families trying to build better lives are all connected — pulling on one affects the others.
There were no simple answers. We’ve always tried to help our kids draw their own conclusions rather than hand them ours. As the five of us moved from one thread to another, the conversation was thoughtful, open, and at times spirited. We weren’t always in agreement.
And this is where Charlie’s guidance is reassuring. Charlie often warned that if everyone accepts the current consensus without questioning it, the consensus itself never improves. It calcifies. Progress depends on people willing to question it and think independently.
I’m part of many herds. Family member. Dad. Entrepreneur. Hockey coach. Health optimizer. Writer. Terrible golfer. Herds offer identity, shared values, and a sense of place. They show up when things get hard. They pass down wisdom. At their best, they make you more than you’d be alone.
The executive who ran the board I mentioned earlier would gather us for a couple of days at a time in a retreat setting. The first few sessions frustrated me — we never seemed to decide anything. Eventually I realized that was the point. He wanted people to think out loud, debate, and wander off the beaten path so he could challenge his own thinking, not confirm it. He understood that deciding too early closes the learning. We all left better. That’s a herd working the way it should.
Yet herds run the same loop we do. A challenge arrives and the defense begins — not because the challenge is wrong, but because the tribe has always protected itself this way.
What’s harder to see is that this response was shaped for a world that no longer exists. Belonging to the tribe once meant survival, and that instinct never left.
But a herd that can’t tolerate dissent doesn’t get smarter. It just gets louder.
I saw Charlie the next day at the mailbox.
Me: I’ve been thinking since our last conversation, how do I know if I’m thinking for myself or just following the herd?
Charlie: Invert, always invert. Don’t ask if you’re thinking for yourself. Ask what you would do if you wanted to never think for yourself. All I want to know is where I’m going to die, so I’ll never go there.
The exercise is simpler than it sounds. Just invert the question. What would you do if you wanted the opposite outcome? Then don’t do those things.
I don’t want to be overweight. What would I do if I wanted to be overweight?
I want my kids to be confident and capable. What would I do if I wanted to raise insecure, dependent kids?
I want my team to trust me as a leader. What would I do if I wanted my team to distrust me?
I want to think independently. What would I do if I wanted to never think for myself?
The answer to the last question, channeling Charlie, might sound something like this. Surround yourself with people who all think alike, and never leave that circle. Read only what confirms what you already believe. Let discomfort be your signal to stop thinking rather than to keep going. Defer to whoever is most confident in the room, because confidence feels like competence. Form your opinions based on who holds them, not why. Protect your social standing at the expense of your own thinking. If you do all of that faithfully, you will never have to think for yourself again, and you will be rewarded for it constantly, right up until the moment you no longer like who you’ve become.
Health is one area where I’ve been confidently wrong more than once. As the science evolves, so does the guidance. The experts I trust most are the ones willing to change their minds when new evidence supports a different conclusion.
At one point, I adopted intermittent fasting for its proposed autophagy benefits, only to learn years later that when autophagy actually kicks in is still largely unknown and likely not within the fasting window I had been following. Meanwhile, the greater risk for an aging person is inadequate protein intake, something my collapsed eating window likely made worse.
More often, I’ve been the beneficiary. Advances in training, recovery, and nutrition that challenged long-held assumptions have meaningfully changed how I experience each day.
It’s almost impossible to push knowledge forward and always be right. At some point, you have to act on your best current thinking, knowing you might be wrong. Being wrong is often part of how we get it right. But that only works if people are willing to be challenged and change course when the evidence supports it. The ideas that prove true raise the mean for everyone else.
For me, the better question has become not whether I’m right, but how I might be wrong.
The discomfort of asking is almost always smaller than the cost of not asking. With AI assistants available to anyone, it’s easier than ever to learn, gain perspective, and widen our understanding. It just requires a willingness to explore.
Charlie Munger died at 99. He joins my Grandpa Charlie and my dog Charlie among the Charlies in my life now gone.
On my right wrist, I wear a band that reads Memento Mori — remember you will die — a reminder that someday I’ll join them.
Useful when certainty outpaces understanding.
In the end, the number of times we were right probably won’t matter much.
But our willingness to question ourselves could. You might just avoid fooling yourself.