Harold sees the value of being cavalier after realizing that all of the smartest and most dedicated people he knew from college were on incredibly conventional, though prestigious, career tracks:
You could almost draw a 2 x 2 matrix with the axes labeled “Courage” and “Capability” and see a vast yawning void where the right upper quadrant ought to be. I scratched my head about this puzzle for a long time, but no explanation was forthcoming.
So let’s tackle a different question: why is Donald Trump so interesting? I don’t mean his politics per se, but rather his personality. In a time when lots of politicians try to brand themselves an outsider to politics, he actually acts like one, for better or worse. He exudes an attitude of “I’ve already made it, I’m gonna do my thing, and maybe people will like it or not.”
And sure, he’s a billionaire, so it’s easy for him to do that sort of thing. But it’s notable that there are 536 billionaires in the US — just two short of the number of Congressmen and Senators — and almost all of them are fairly boring in their interests and activities. Trump, Soros, Musk, and Thiel are the ones that jump out as exhibiting, in very different ways, the sort of agency you’d expect from someone who’s already made it. Sure, most of us have day jobs and families to feed, so you’d expect us to veer closer to convention. But if anyone could be brashly unconventional, it would be billionaires. And yet that’s not what we observe.
My sense is that aristocrats were way more interesting, and this is not unrelated to their remarkable intellectual productivity. Darwin noodled around with naturalism after abandoning a career in medicine. Edward Gibbon wrote his famous Decline and Fall only after several equally ambitious failures, such as a panoramic history of Switzerland and a survey of contemporary English literature. These were not the equivalents of a grad student carefully publishing some cautious extensions of his PI’s work to get some guaranteed publications, they were bold, imaginative, and ambitious.
In a world where more people than ever could live materially quite comfortably, it seems notable that so few of our elites are demonstrating that level of ambition. It’s as though we had all the tools necessary to support enormous levels of human agency, and decided to just sit on them.
There are probably lots of causes for this shift, from changes in culture to differences in education. But one striking difference is that for past generations of elites, it was common to take a position as a military officer while growing up — whereas today, outside maybe Israel and a few other countries, it’s unheard of. Being a lieutenant in a cavalry regiment was as common then is going to grad school is today.
Part of this, sure, was carrying on the tradition of the nobility as being responsible for physical security. But part of it, too, is the sense that command over men in situations that matter fundamentally changes the way you see the world. As a leader, you have to be responsible both for planning and for execution. You have to closely monitor how the men under your command are behaving. And it forces you into a frame of mind where taking initiative and making decisions are the default, rather than the exception.
We don’t really have analogues of this anymore. Pretty much every prestigious career track involves not personal command but prolonged institutional subordination.