Unreasonable Confidence

Jul 26, 2026

The following is one of my most intense convictions, if not the most intense: there are far too many confident people on this planet. I would go so far as to characterize the overwhelming majority of human beings as unreasonably confident.

Admittedly, I’m cynical. I’m slow to believe. I want evidence. Not just a little proof. I want a pattern of evidence that’s been kicked and stepped on. I want a history that’s been shaken, poked, and prodded. I want testimony that holds up to teams of bloodthirsty, greedy-as-hell Ivy League trial attorneys.

I’m only really confident in the premise that there are too many confident people. Whenever I run across someone projecting confidence in the real world, my hackles stand at attention. Who is this joker? I wonder. What’s that smile doing on his face? Where did he get that upright posture, and why is that gleam in his eye so shiny? How long before he tries to sell me a monorail? At what point is he going to invite me to his church or his MLM or his crypto workshop? Who the fuck does he think he is?

A reasonable question when you come across anyone who projects “confidence.”

You could argue that my distrust of confident people is more about my own insecurity. Fair enough. But here’s the thing. I own my insecurity. I wear it like a glittering badge of dishonor. All Kinds of Funny could easily be called The Great Many Humiliations of Norman T. Leonard or A Brief History of Norman T. Leonard Being Wrong and Getting Physically and Existentially Injured.

Most “confident” people I come across have no insecurities to speak of—at least no insecurities they will speak of. They’re the kind of people who say stupid shit like, “My greatest weakness is that I’m a perfectionist” or “People often mistake my confidence for arrogance,” which is like saying people mistake your grease fire for an unusually warm kitchen.

Shortly after I finished grad school, just before the 2008 housing crash, I was still bartending in a restaurant near Coto de Caza. Pro athletes, C-suite executives, and The Real Housewives of Orange County were regulars. So were a lot of mortgage brokers. One in particular stood out: a twenty-something kid who had bought three Lamborghinis in different colors and wore tailored suits to match each of these vehicular compensations.

He regularly ordered expensive bottles of Cab but never finished them, and he paid his tab with a titanium American Express card—which was issued by invitation only, he liked to tell us. He treated the servers like servants, particularly the cocktail waitresses who, to their credit, were wholly unimpressed with his unreasonable confidence.

The last time I saw him, the well-done filet and Opus One had been replaced by a Coke and a side of fries. I was a vigilant bartender. I liked to keep things neat and orderly, and I was obsessive about clearing used cocktail napkins from the bar. Apparently, the kid had wrapped his retainer in one while he ate.

I threw it away.

When he realized what had happened, he called me a dipshit, demanded to know whether I had any idea how much a retainer cost, and then began to weep. Tears of confidence, I imagine. Try to disguise insecurity as certainty, and it’ll come out sideways, usually through your tear ducts.

Your typical mortgage broker after he misplaces his retainer.

While I was making notes for this treatise on unreasonable confidence, I asked my daughter who the most confident person she knew was. “Banjo,” she said. Banjo isn’t a person. He’s a dog, and he looks like this:

My daughter was right. Banjo is confident. Mostly. He’s unreasonably confident when he barks his goddamn head off at passersby in the interest of protecting our homestead. No reasonable person looks at this dog and feels anything resembling fear or intimidation. In fact, mostly his barking inspires laughter and pity. Aside from this ongoing delusion of grandeur, Banjo’s confidence is entirely warranted.

Occasionally, I take him around town, to the hardware store or to an outdoor mall, and you’ve never seen a dog’s tail wag with as much fervor. He walks up to every person, fully confident that he’s going to bring joy to their day, which only makes his tail wag more. So far, every available data point suggests he’s right. Going anywhere with Banjo is like strolling through Nashville with Dolly Parton. Nothing but love and joy and happiness.

While I appreciate my daughter’s take on Banjo and his canine confidence, I’m never going to have a windshield-wiper tail or floppy ears or (I hope) a body that resembles a giant, furry, uncircumcised penis that disarms the coldest of hearts. Physically, Banjo offers me little practical guidance. His approach to people, however, is worth considering.

I see something similar in my wife, who leads a team of her own. I’ve worked with all kinds of leaders (and so-called leaders), and few of them come close to my wife’s impact. And to the best of my knowledge, she doesn’t attend Tony Robbins seminars, she hasn’t read The 7 Habits of Highly Effective People, and she’s never identified her “nonnegotiables.” This is what she does. She loves people. And she does so with all the enthusiasm of a basset hound. Some people find her energy off-putting but just initially. Sooner or later, they recognize her authenticity, and they return her love—and then some.

This is the difference between her confidence, which I admire, and the confidence of most people, which I detest. Her confidence is not singular. It’s not predicated on these sorts of claims: “I can do this… I can do that… Me! Me! Me!… I am the only one…” That sort of “confidence” is typical of politicians, cult leaders, AI innovators, and conspiracy theorists who “do their own research.”

My wife’s confidence is not about her. She’s not interested in being the savior. Most “confident” people want you to believe in them. My wife makes you believe in us. And that’s as reasonable as confidence gets.

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