Stoicism On Holiday

Ryan Holiday, Stoicism, and some ramblings on historical vs. modern context.

Sometimes, it really does pay to read your own writing. Ryan Holiday is a prime example of why.

Holiday is an author, a marketer, and the founder of the Daily Stoic, one of the most widely read Internet sources on the philosophy of Stoicism. His books (some of which sit on my bookshelf) include Ego is the Enemy, The Obstacle is the Way, and Discipline is Destiny: The Power of Self-Control. And yet, despite a deep bank of historical knowledge and a years-long career in attempting to distill the wisdom of Stoic figures, including Seneca and Marcus Aurelius, into insights for modern audiences, Holiday is not immune to having those Stoic beliefs overridden by political negative polarization. In a recent widely-criticized video, Holiday reacts to Ivanka Trump’s praise for the classic Stoic text, Marcus Aurelius’ Meditations, criticizing Trump and heavily implying that if Ivanka were a true Stoic, she would be doing a better job of confronting her father, Donald Trump.

Why is this outburst from Holiday’s outburst so odd? Leave aside the obvious dunk of an advocate of stoicism being decidedly unstoic. Leave aside our current political discourse’s annoying tendency to reward these sorts of outbursts from generally reasonable and intellectual people. There’s something else here.

This isn’t really about dunking on Ryan Holiday. In fact, I’ll go further — I think if you’re interested in modern summations of the philosophy of Stoicism, Ryan’s work is worth reading. It’s simple intellectual adulthood to be able to see and appreciate someone’s insights on a given issue while also not taking their thoughts on other issues. This is also a good skill for blood pressure regulation.

There’s a deeper lesson for young conservatives to be taken from the Holiday case study. It’s about historical and modern context. As author and merchant marine John Konrad IV (a X follow well-worth your time) notes about Holiday, “[Ryan] can plug real, useful historical lessons into almost any problem… he genuinely wants to fix America, but he is unbalanced. His historical context runs deep. His modern context is superficial.”

I think that’s spot on, and yet I can’t help but think: if I had to describe the negative tendencies of being a young person in politics, I’d probably end up saying something like: “Our modern context runs deep. Our historical context is superficial.”

This may seem odd if you’re not the social media type. But if you’re terminally online, as I’m willing to bet many of the people reading this are, you know what I mean. You probably have more modern context than any other 20-25-year-old in human history. It’s at our fingertips every day — I probably scrolled through 100 tweets while writing this article. I have so much modern context. I don’t have to go anywhere to get it. I have it, I create it, and I am shaped by it.

But historical context? I have to go looking for that. I generally have to read books and talk to people who aren’t 25 to get useful insight on the relevance of the past, regarding everything from Marcus Aurelius to Spirit Airlines. And the temptation to simply regurgitate subpar modern context can lead people to all kinds of mistakes, from backwards economics to Holiday’s bizarre guilt-by-Trump-sociation.

Holiday’s malaise may not be that of the average American under 30. But it doesn’t mean we can’t learn something from it. Further, there’s one specific piece of historical context that Holiday doesn’t seem to find particularly compelling: religion. Ryan is a self-described secular progressive who went on a separate but equally baffling recent video segment about Ted Lasso being a replacement for catechizing young people because, yes, that’s definitely comparable.

These two clips aren’t technically related. But I think they both epitomize a dilemma for the secular 21st-century individual. If you’re a secular Stoic, you can pure-rationality-exercise your way through a bad quarter or a failed exam. But negative political polarization or the desire to have your children not be nihilists can unravel you. And why wouldn’t it? Emotions are real - and Stoicism detached from a transcendent moral order is proving less than stellar at adjusting for this.

So where does that leave us? As advocates for a transcendent moral order, we have something that’s chock-full of both historical and modern context. Historic Christianity certainly functions as a context for faithful witness and defending tradition over millennia. But Christianity also has a lot of modern context to offer. It has a lot to say about the economy, technology, negative polarization, hatred, and the limits of cold rationality. It is incumbent upon us to understand both of those contexts - to learn about and develop them for the issues we’re confronted with. That, as the Apostle Paul puts it, is our “rational service.”

Marcus Aurelius notably described Christians’ willingness to die as Roman martyrs as obstinacy. That might make sense if you’re an emperor. And yet it would be Christianity that outlasted the emperor, built the moral structure of the West, and helped create a civilization that’s so prosperous that it can fund museums with Aurelius exhibits off the largess of others. That is, in fact, not pointless obstinacy. It’s the fruit of a rational faith.

That is a comforting thought and an encouragement to get in the arena. It is Stoicism that exhorts you every day: memento mori — remember that you will die. It is Christianity that exhorts you every day: remember that not only will you live, but live eternally, and answer for that life. That is the applied philosophy that defends human dignity, lifts up the oppressed, and drives civilization forward. So let’s all do a little more of that.

What I’m Reading

JPMorgan’s Jamie Dimon on American growth

Wrong policies and bureaucratic red tape can stifle growth and progress. It already has, for too long. We must all remember that, despite our extraordinary blessings, the United States does not have a divine right to success.

Stephen Kent on why no, Lord of the Rings isn’t pagan

Just because no one takes the Eucharist in Gondor does not mean Tolkien’s world must be pagan. Quite the contrary. Middle-earth in all its strangeness speaks to the imaginative hunger of people’s hearts, calling them to see with fresh eyes the Truth they so often take for granted.

Doug Wilson on AI, Sabbath, and work

God created man for meaningful work. The fourth commandment has two halves. We are all familiar with the requirement that we take a day of rest before the Lord. But the other half of the commandment requires us to work for six.

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That’s all for now. Signing off. -Isaac