Ryan Holiday Has This All Wrong

G.K. Chesterton's fence, Studio Ghibli and American politics

Stoic on Stoic violence! I am a big Ryan Holiday fan. As I write this I’m surrounded by at least five of Ryan’s books and his work is part of why I do this at all. But part of philosophy as Seneca rightly understood is that you have to develop ideas, quotes, thoughts, and perspectives of your own and not rely on repeating back the thoughts of other people.

When you start doing this, you’ll have disagreements (hopefully). So here’s one: Ryan Holiday does not understand politics.

I’m going to show you Ryan Holiday’s strange analysis of liberalism vs conservatism and explain what he’s missing that could lend to a more constructive modern political ethic. This will be a journey from G.K. Chesterton to an obscure Studio Ghibli film and is all about the battle between the head and the heart.

Openness versus rigidity.

Boundaries versus freewheeling through life.

And I won’t get all of this right or cover all my bases. People write entire books about this subject, and I want to try and float some of my thoughts and leave room for revisiting the subject if it generates some interest and discussion within our little community.

On the Daily Stoic podcast of January 21st, 2025, Ryan said this (and I cleaned up his verbal delivery a bit so it’s easier to follow in writing):

“I remember as a young man, my dad said something to me. He said, “You know, if you're not liberal when you're young — you have no heart…and if you're not conservative when you're older — you have no brain.” Look, the broad strokes of that message make sense. Your idealism when you're young can (it turns out) not be based on anything real. And as you get older and you experience things….you can become a little cynical.”

Right off the bat, Holiday is twisting words in a pretty big way. This saying that Ryan’s father recycled is quite common, and you’ve probably heard it a million times. The saying has been misattributed to a dozen political figures since the 19th century. That alone is a red flag because the way liberal and conservative would be defined has changed a great deal since say, the French Revolution.

But I’ve heard anyone suggest that the young liberal’s heart = idealism, and the older conservative’s brain = cynicism.

You usually hear this aphorism used to communicate how someone will get more “conservative” when they start paying property taxes or choosing a home based on the quality of the school district. Responsible decisionmaking.

Let’s now try to define liberal. Being liberal is not about a set of specific policy ideas, pronouns, or tax rates. To be liberal is to have a friendly disposition toward openness, both to new experiences and new ideas. This person is more prone to see boundaries as restrictions and view freedom through the lens of choice. They answer requests for advice or direction with, “I dunno, whatever makes you happy.”

Conservative….I think is trickier, because the American conservative tradition is rooted in classical liberalism. My favorite quote for this is from Bill Buckley, who said “A conservative is someone who stands athwart history, yelling Stop, at a time when no one is inclined to do so or to have much patience with those who so urge it.” A conservative tends to value tradition and loyalty above openness, and they see boundaries as either representing timeless truth or reason. The 19th-century English author G.K. Chesterton has this long observation about people who want to reform systems (liberals, usually), and it’s quite long, but the short version of his analysis is — Don't ever take a fence down until you know the reason it was put up.

GK Chesterton’s fence

Ryan Holiday is a wonderfully complex person when it comes to politics. He is a former Los Angeles PR flak who moved his life to a small town in Austin, Texas. He is a solid free-speech advocate, a critic of oversensitivity and cancel culture, but he’s also a pretty boilerplate MSNBC Democrat who layers Stoicism atop his advocacy on transgender issues, admiration for Republican members of the Jan 6 Committee and promoting the recently pardoned Dr. Anthony Fauci as an American hero.

Holiday continues:

“You have to become a bit more pragmatic and realistic. But as it happens, this quote, which was popular in talk radio circles in the 1990s, actually dates back to the 1800s. There's also something terribly, terribly sad about it. Something I think you want to be careful about when you're young, it's good that you're open-hearted and idealistic, that you have values and principles. Don't let the world steal those from you. Don't give in to nihilism. Gandhi was once asked what worries him the most… and he said, “The hardheartedness of the educated is a matter of constant concern and sorrow to me.” You have to keep that openness and that goodness inside you. You have to carry the fire.”

Young people are not what they used to be. We tend to think of those under 30 as Luke Skywalker-types, dreaming of space and getting away from home to build a fantastical life. But…..what we know from most available research is that younger generations are more nihilist and cynical than ever before. A major multi-country study conducted found that over fifty percent of young people believe that humanity is doomed, with many of them citing the climate crisis, civil rights abuses, and democratic decline as their reasons. Gen Z and some younger Millennials are the first cohort we’ve ever seen to promote not having children as a form of mercy, for fear of a dystopian future.

They aren’t forming families. They think future kids need to be saved from existence. They have record low belief in God or the transcendent. They have less community ties, less active sex lives, and take fewer risks than any generation before them. Not exactly beacons of idealism and hope, being stepped on by “cynical” old conservatives.

Oh and by the way, millennials are the most educated generation in history. Gen Z is on track to surpass them by 2030. So something in their education is clearly turning them against existence itself.

But I can’t let Boomers off the hook here. In short, their generation raised these young people and popularized “whatever makes you happy” as a way of life. This has failed miserably, whereas the Silent Generation and Greatest Generation might have understood more clearly that duty and obligation tend to be more reliable founts of happiness and purpose.

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Holiday mentioned Gandhi and his critique of the hard heats of the educated. Who is Holiday referring to here? Is he saying that older people have hard hearts due to their education in life at the school of hard knocks…or is he saying formal education produces a cold exterior? I think Holiday meant the former, referring to people with more life experience AKA the conservatives according to the aphorism his Father passed on.

But all available evidence points in the opposite direction. First, Gandhi was literally referencing formal education. Gandhi’s well-documented concern was that modern education is riddled with disconnections that stifle an individual's moral development and fragment the concept of a unified self. From early schooling to higher education, this system widens the divide between intellect and emotion, theory and practice, mental and physical effort, and reason and feeling—effectively detaching thought from experience. As he wrote in Young India (1925), "I would develop in the child his hands, his brain, and his soul. The hands have almost atrophied. The soul has been altogether ignored."

Does anyone think American liberals are particularly concerned with the soul compared to your archetypal conservative?

One of Ryan Holiday’s most useful insights into the stoic philosophy of Marcus Aurelius is that you don’t need to have opinions about everything. We talk about that here as well, drawing on both Aurelius and C.S. Lewis. But my worry remains that Holiday wants his audience to always withhold moral judgments on activities he considers fine and good. He abides by that attitude of “whatever makes you happy” and a libertarian “no one is being harmed” ethos when it comes to lifestyle, but also wants his readers to be civically engaged and activist.

I think we just have sincere disagreements about what constitutes harm or a civic good.

So what are we to do?

Something that I believe has changed in the liberal-conservative dynamic is that young people are increasingly starved for old, reliable, and time-tested ideas and institutions. The radical liberal individualism that bloomed from the 1970s onward has left young people estranged from the past, and it’s why they have no sense of the future they’re supposed to be part of.

In Studio Ghibli’s highly underrated film, From Up On Poppy Hill, children in 1960s post-war Japan are fighting school administrators who want to tear down an old clubhouse on school grounds. After Japanese imperial fascism and World War II, older folks are rapidly trying to wash away the past and create a clean slate. The kids, however, are on the opposite end of this debate.

“Destroy the old and you destroy our memory of the past. Don't you care about the people who lived and died before us? There's no future for people who worship the future and forget the past!” shouts Shun, a young man in From Up On Poppy Hill.

The kids rally for tradition and history against older folks eager to move on from it. Studio Ghibli’s “From Up On Poppy Hill”

Don’t worship the future and every promise of progress, but be open to its inevitable arrival. Know the past, respect the fences that were built by previous generations, and understand them deeply before you tear them down.

Being conservative does not mean you have no heart, in fact, you might have more heart and soul than the average person. Being liberal does not mean you have no brain, it could be an indicator of just how deeply imaginative you are in seeing what’s possible.

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