Modernity's leadership crisis
Without proper leadership, the world devolves into a significantly worse place
I never wanted to mention names like Andrew Tate or the Hawk Tuah girl on my blog, but I’m going to subject you to them once, in that sentence. We’re done now. You only have even heard their names and others like them because of modernity’s leadership crisis. It’s palpable and pernicious. If we had sufficient real leaders, if people running things in government, media, business and culture weren’t largely checked-out, coasting, or just plain fraudulent, there wouldn’t be space for such things. But we don’t, and so celebrity spectacle fills the void.
It’s a simple law of human nature: leadership abhors a vacuum. If legitimate leaders don’t rise, something else will. That ‘something else’ turns out to be whoever is the loudest in media formats optimized for maximum engagement. In an earlier age, this phenomenon would have been constrained to town squares and tabloids. These people were considered lunatics, low status and mostly ignored. Today, we scale them effortlessly and put clowns on stage 24/7. We’re extraordinarily dumb to have let this happen. But this is of course symptomatic of something larger: our leadership crisis. Let’s discuss a few areas everyone can understand.
Leadership in government
America has been increasingly governed by a gerontocracy with elderly leaders clinging to power well beyond their time, (some literally falling over outside our institutions) surrounded by bureaucratic NPCs who exist purely to keep the machine running, not to question its programming. These NPCs have names, of course, and LinkedIn pages full of credentials, but the effect remains the same: they’re propping up barely sentient and often corrupted officials.
And it’s not that wisdom doesn’t come with age. Of course it does. But so does the tendency to mistake inertia for stability. At a certain point what passes for leadership is just custodianship ensuring existing structures, however full of rot, persist. What’s missing is vision, courage, a willingness to make decisions that are right but not necessarily popular. Also as I’ve written on before in a healthy world people would die helping, not clutching the levers of power. We’ve decided to mostly stop doing this. To our own detriment, very few are planting trees they will never enjoy the shade of (this is what ultimately makes great nations).
It took just 410 days to build the Empire State Building and 1,604 days (4 years, 4 months) to finish the Golden Gate Bridge. Now ambitious projects sit unfinished a decade later, while we have far better technology. The bureaucratic stagnation is palpable, a massive failure of leadership to get out of its own way. Meanwhile, half the population still wonders how we got here.
Leadership in media
The media business has become a system optimized less for what’s morally correct or even truth than for velocity. Attention has been financialized, and the people steering the ship aren’t Walter Cronkite or David Brinkley, they’re editorial teams analyzing engagement metrics and encouraging writers to publish that which creates outrage. I wrote a longer piece about this in the subprime attention bubble, but the point here is simple: when your industry rewards virality and clickbait over substance, the outcome is less real journalism and more a perpetual chase of low quality attention.
This too is a failure of leadership. Not because there aren’t good journalists, there are, but because our modern attention ecosystem elevates voices indiscriminately. The most successful figures or brands aren’t necessarily those any of us who are still sane would call real leaders, instead it’s quite the opposite. This happens in many areas that require an audience and it turns out that’s many.
Leadership in art and music
The cultural institutions that once defined what was important, daring, interesting or perhaps just from people who were authentic now don’t lead at all. The underground is algorithmically suppressed, and the mainstream is a risk-averse nostalgia machine that keeps people stuck in an infantilized aesthetic. We have millions of grown adults consuming what is essentially boxed mac and cheese aural dinners on music streaming services. And how many reboots, sequels, and repackaged trends from 20 years ago do we need before we admit that creativity just isn’t coming from the places it used to? It’s honestly a joke amongst anyone with even the slightest levels of metacognition (fun note: both the left and the right agree Hollywood is a mess and the reasons actually converge). We have dismal MBA bureaucrats leading creative sectors, which might work fine for making widgets but the process for art is so different. It couldn’t be bleaker.
This is personal to me. I remember a time when art felt experimental, when artists normal people loved weren’t just pre-sorted into a playlist by Spotify’s recommendation engine, keeping most people’s musical taste stuck. Leadership in art used to mean taking creative risks or perhaps just promoting competence. Now it mostly means pattern matching against the past and creating spectacle. And it’s not just tastemakers, even individuals have ceded agency here. Anyone could wake up tomorrow and choose differently, but they won’t. Just like they probably won’t start eating better or going to the gym. The reasons are similar. Better leadership or mentorship in their personal life might help.
Leadership in business
Business is one of the few places where proper leadership still does frequently exist, mostly because it has to. Companies that are too fraudulent or too stagnant eventually fail. But even here, there’s a creeping admiration for spammers and grifters, those who don’t build but extract, who think of business less as a way to create anything and more as a series of arbitrage opportunities.

Many do actually consider these people leaders. But that’s only because, in the absence of real leadership, people accept its shadow.
Leadership in family
I grew up without a father, because he died young and I didn’t have to chance to really know him. While I’m personally unlucky, I’m hardly alone in this situation. Many parents particularly in the baby boomer cohort were absent or ignored the changing world around them when providing guidance. I’ve written on this before, where oddly adults do not wish to advantage their own family wherever possible. It’s not lindy behavior.
The birthrate is currently at historic lows which is also a massive failure of familial leadership (probably the largest possible signal). Why was our generation almost never encouraged to have large families? Why were we given cynical guidance such as “do whatever you want” instead of messaging and support to build legacy? Of course it still happens, but in my experience talking to 30 and 40-something friends it’s very common proper parental leadership was absent or just lacking certain values religious or historic figures would have seen as virtuous. Our postmodern era mostly throws away the past and doesn’t take enough time to consider what our ancestors got right.
The result
So we arrive at a point vapid figures are worshipped and we have ‘leaders’ those from other eras of history would look down upon. An endless parade of engagement-maximalist figures who step into the void left by absent leadership of the managerial and even gilded classes. Not because they’re offering anything of real substance, but because, in a system where everyone else is either afraid or asleep, they’re at least there.
It’s easy to laugh at the absurdity of this situation. Harder to ask why it exists, or what we can do to make things better. More nihilism to ignore. What we badly need is for you to lead us.
Nice read as always, I think one of the most observable voids of leadership you didn't touch on in this article is mentorship at work. People in my cohort (let's call it 90's babies) were/are told by their parents that you go to school, get a job, you show up and listen to your superiors, and in turn they pass their wisdom down on you to help you navigate the great uncertainty that is a career. In speaking to friends/colleagues, I can't think of a system that works less like those people envision. My colleagues are demanded to return to full time office work only to show up to an office where the executives only come in a few days a week and hardly have time to interact with you, instead asking you to simply sit around and be available to them when necessary. "Mentoring" to them seemingly means "sit on this call I am on and just listen" and I guess in turn you suddenly understand exactly what your supposed to be doing? This has, in my observation, helped create a generation of workers who are so detached from their job/company/colleagues and in turn void of any meaning from work, which perpetuates a nihilistic cycle where they feel powerless to create anything in the world around them. I think this is a huge problem in the "leadership" of our society who have zero interest in planting trees but instead tell us to be grateful for the shade their trees provide, not realizing the lack of sunlight isn't letting us plant any of our own.
“risk-averse nostalgia machine”. I’ve been wanting to write about that and you nailed it in one phrase!