The Annuity

1.22.2026

“Show me the incentive and I will show you the outcome.”—Charlie Munger

Some say men don’t mature until they’re fifty years old.

What is meant by mature isn’t always well-defined, but after a few decades of making the exact same mistakes we seem to refine and grasp it.

I polish a certain finish now, and I’m not yet forty-seven. I’ve always had a fascination with whatever women meant when they said “mature.”

I don’t know why. Something about the manliness of it.

Even as a grade school student carrying a briefcase to Barrett Elementary, back when Alex P. Keaton was my mentor and childhood hero, I recall a civilized dissatisfaction with adolescence.

Plainly, it was vulgar, and there was little money in it.

When asked what I wanted to be when I grew up, I almost always answered, ‘an adult.’ I wanted to be a successful man who controlled his time.

There’s something stylish I observe in a man’s evolution.

Men calm and settle, become more robust and rich in detail, often in value, like an old Mourvèdre. We age well, especially when we take care of ourselves.

The best of us have learned and applied the lessons we were taught.

I think when we’re young we’re preoccupied with silly things like freedom and money, without a care in the world to understand the foundations of either.

We still think it’s about the having and not the knowing.

Grown men know things. It’s what makes them attractive to people who have things. I also believe it’s more than that for a certain class of man.

I don’t have a name for this man, but let’s call him “the gentleman.”

For this man, knowing isn’t about having so much as being impervious to the poverty of need itself. Such a man attracts everything and wants nothing.

Whatever may be wanted is in the process of being had.

This is a species of animal I’ve long admired, since my late father demonstrated to my brother and me the concept. Let’s observe.

I’ll do my best to explain the value of him.

His priorities are his priority. He’s never disconnected from them. Every action taken reflects what he values. He dreams in decades and learns to plan accordingly. For him, very little is for show.

He understands the most valuable thing to his future is returns.

To accomplish this, the gentleman is known to curate expert talent to assist him in his plans for world domination. Only a fool would try to do it alone.

His talents include consultants, cutters, tailors, trainers, therapists, bartenders, money managers, advisors, lawyers, investors, and one or two irregulars.

Such talents are not expenditures, but investments in his future.

There’s something to be said about a man’s tailor, by the way.

I want to come back to this idea that a gentleman is not merely a well-mannered snob. He’s more a creature of self-possession than he is a nice man.

Self-possession is a powerful scent people associate with security, both emotional and financial. Self-securing people are happier, more productive, often smile or joke more, and are generally pleasant.

For this reason, gentlemen are perceived to be nice.

A man who needs little from others has time to be patient and generous to those who need a lot. One predictable trait of civilizations is the largesse of poor, great men, and the cruelty of rich, small ones. And it’s obvious why.

Money doesn’t buy class.

Politeness and dandyism are not gentlemanly traits, but personal effects. A gentleman is more of a punisher of rudeness and cruelty, than an eloquent sycophant in the name of good manners. The only values they espouse are their own.

The traits of gentlemen are deferred annuities from a single investment in oneself. It’s what enables them to feel differently when comparing them to other men. Gentlemen feel like something, something oaky and certain.

It’s why successful men admire and imitate them.

If you want to raise strong boys strong men are required. It isn’t because strong men are tough. It’s because strong people enforce strong realities.

Gentlemen are unafraid of the truth, even when it slights them. It’s a signal to them they need to get better. They don’t take it personally, which I admit was difficult for me before I matured. It wasn’t obvious at the time.

No person likes to be slighted— but that’s the thing.

If you’re capable of being slighted, the problem might not be with the one who did the slighting, but in some untidy thing of your own making. Many men believe it to be the other way around and stumble.

People should just be nice. Except most people are wearing nose and glasses disguises.

They’d prefer it if you said something kind about the disguise, not comment truthfully on the face underneath. Here, being kind isn’t kindness but mercifulness.

It’s encouraging a man to not deal with problems he’d be less likely to have if he were ever told the truth. At scale, this looks like a society littered with liars, losers, crooks, punks, and sycophants.

I’d also note, it’s a society very dangerous for women.

Maturity makes men something more. It makes us strong, capable of correcting errors and changing, even sacrificing ourselves for others at the drop of a dime.

The 21st century gentleman isn’t lost, but hidden. He’s taking time off from society. It might be a shame, but it’s become the world we live in.

You can still find this odd creature where he’s understood and respected.

He isn’t too far away.