The Value of Being Cavalier

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone…

-Robert Heinlein


I recently went to my sixth college reunion. It was great to catch up with old friends, and it was also a pretty fascinating experience to see how people’s lives have branched out. At this early stage in life, it’s not totally obvious how everyone’s going to turn out, but it’s certainly starting to become clear just where people are placing their bets at this early stage in their career.

Towards the end, as I was reflecting on the weekend’s events, I noticed a remarkable thing: all of the smartest and most dedicated people I caught up with were on incredibly conventional, though prestigious, career tracks. People were going to Wall Street, people were getting into excellent law schools and med schools,and so on. But nobody I know was dropping out of school to start the next Apple, or working on revolutionary research that they were excited to talk about. The few people who were not on one of these conventional career tracks all seemed pretty dissatisfied with their lives, and framed their predicament as trying to find their way out of what they were currently doing to something more conventionally prestigious and stable.

This seemed really strange to me. Certainly, the world needed good lawyers and doctors and so on. But the world needed the next generation of great men as well. And out of the best and the brightest in my class – in one of the top universities in the country – it seemed like nobody was really stepping up to that particular challenge. 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 almost all of them are quite boring. 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 or 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. In medical school, law school, and grad school, you toil under the eye of faceless representatives of massive institutions, whether these be senior physicians or law firm partners or PIs. You don’t have any subordinates to manage, unless it’s the occasional junior medical student or summer research intern. Furthermore, even this subordination is not personal, under someone who has been trained in command, but rather institutional, under superiors who are themselves slotted into institutional roles and don’t always have a great deal of autonomy. This is least true in grad school, where the apprenticeship model is still somewhat alive, but even there, many grad school friends have told me that they see their PIs more like a boss that they try to interact with infrequently then as a valued mentor.

Even business school, which is probably the closest thing we have to pure leadership training, follows this pattern. The most common route to business school involves working as an analyst in a Wall Street firm or other prestigious financial institution. And just like first-year law students or medical interns, this basically involves institutional subordination, not command. A telling story: my friend who is now in business school ended up with a brief stint in charge of a small department, but only by accident. He had intended to continue as a venture capital analyst, but when his contract wasn’t renewed at the end of the standard two-year gig, he found a position in one of their portfolio companies. So rather than command being an expected part of an elite upbringing, it’s reserved only for the elites who fall off the ladder! No wonder, then, that our elites tend less towards leadership and independent thinking, and languish instead in institutional learned helplessness, working as various flavors of Company Men.

Some of my friends have a strong intuition that more people should lift weights. They argue not only for the health benefits but also for the changes in mood and outlook that are supposed to come with it – more positivity and a greater overall sense of ability to accomplish things. I suspect that given this trend in elite education, it may be worth thinking about having the same attitude towards small group leadership. At minimum, we’d end up picking up some skills that might be useful in jobs. But even more valuable, I think we’d end up picking up an aristocratic stance towards life that is necessary for real accomplishment.