Philosophy

The real source of freedom

In The Virtues of War Alexander the Great comes to a river crossing only to be stopped by a philosopher who’s standing in his way. Irritated, a man from Alexander’s crew shouts, “This man has conquered the world! What have you done?” Unmoved, the philosopher looks at him and says, “I have conquered the need to conquer the world.”

Though a fictional conversation, it’s an accurate representation of the difference between Alexander the Great and Diogenes the Cynic. Unlike Alexander, Diogenes wasn’t concerned with his image or his ego. He had few wants. He was more powerful than the ruler of the world—because he was the ruler of himself.

Last month I read and took notes on Ryan Holiday’s Discipline is Destiny. For this post, I filtered out everything but a few key takeaways and tied in ideas from The Daily Stoic and Ego is the Enemy.

Ambition Requires Balance

Ambition, Ryan writes, can easily become an addiction. And it’s the worst kind. Because, unlike gluttony or drinking, society rewards ambition. When it comes to successful people, he says, “we don’t ask them what they are doing or why they are doing it, we only ask them how they do it. We conveniently ignore how little satisfaction their accomplishments bring them, how miserable most of them are, and how miserable they tend to make everyone around them.”

It’s important to note that ambition is a good thing; what’s harmful is unfettered ambition. It’s the millionaire who has time for everyone except his own family. It’s the professional athlete who won’t retire. This isn’t freedom—it’s slavery. Slavery to ambition. On the flip side, however, lying around all day with no aspirations is not ideal either.

Ambition, like virtue, requires balance. It requires what Aristotle called the “golden mean”—the middle ground between excess and deficiency. For example, when it comes to pride, the virtuous person isn’t excessively proud, but neither is she excessively humble. She has a modest, self-respecting confidence. The same with courage—the courageous person is somewhere between recklessness and cowardice.

And living within this golden mean is easier when we’re aware of what we—not other people—value.

What We Actually Require

The All-Star forward Kawhi Leonard signed a four-year contract with the L.A. Clippers for $176 million. Still, Ryan writes, he drives his 1997 Chevy Tahoe that he’s had since high school. Not because he’s cheap, but because, “the things that matter to [him] are cheap”. 

When it comes to money, all you really need is enough to not have to do what you don’t want to do, and enough to stick with your main thing (e.g. painting, coding, writing, fund-raising, filming, care-taking—whatever it is that gets you out of bed in the morning). If we don’t know the answer to how much money is enough, the default answer becomes more.

Again, it’s a balance. Extreme generosity on one end, extreme greed on the other. If you give away everything you own, it would be impossible for you to live a good life and flourish. You would end up depriving yourself, and the world, of your best. On the flip side, if you sweat every penny or are a slave to consumption, you’re also not doing yourself, or the world, any good.

Self-discipline, temperance, moderation, whatever you want to call it, is not about deprivation. It’s an opportunity for freedom. “In the last analysis,” Bernard Baruch said, “our only freedom is the freedom to discipline ourselves.”

Unrestrained Moderation

Marcus Aurelius was the literal ruler of the world. He had more responsibilities than anyone. Yet he would remind himself to “not be all about business.” To have “unrestrained moderation” in all things. Not to be too selfless or too selfish, not to be too timid or too reckless, not to work too hard or too little. “Not to be constantly telling people (or writing them) that I’m too busy, unless I really am. Similarly, not to always be ducking my responsibility to the people around me because of ‘pressing business.’”

What’s incredible is that he had unlimited wealth and power, yet his focus was on being a good person. “Just that you do the right thing,” he told himself, “the rest doesn’t matter. Cold or warm. Tired or well-rested. Despised or honored.” He knew, like Diogenes the Cynic, that good character—not money or power—was the real source of freedom.

Imitation and going deeper

My weekly newsletter is a mashup of a small number of other newsletters I read and enjoy. Billy Oppenheimer’s Six at Six showed me how to make each email thematic, and Ryan Holiday’s Daily Stoic emails (which I’ve read nearly every day since 2016) taught me how to connect Stoicism to different topics. Two other newsletters that have given me ideas are Tim Ferris’s 5-Bullet Friday (where I got the idea to include a quotes section), and Austin Kleon’s newsletter of 10 things worth sharing (where I got the idea for a monthly Top 10 list).

This week’s blog is about innovating by imitating and going deeper.

Extend the line

Bob Dylan is regarded as one of the greatest songwriters of all time. At 81 years old, with a career spanning more than 6 decades, he’s still writing, recording, and performing. He’s become an object of study: where does his creativity come from? 

“These songs don’t come out of thin air,” he said. They are the result of years spent listening to traditional music, and singing the same songs over and over. He elaborated:

“If you sang ‘John Henry’ as many times as me—‘John Henry was a steel-driving man / Died with a hammer in his hand / John Henry said a man ain’t nothin’ but a man / Before I let that steam drill drive me down / I’ll die with that hammer in my hand.’ If you had sung that song as many times as I did, you’d have written, ‘How many roads must a man walk down?’ too. All these songs are connected. I just opened up a different door in a different kind of way. . . . I thought I was just extending the line.”

(Similar to The Adjacent Possible)

Build on Top of Something

A few weeks ago, I wrote about how Hal Mumme revolutionized American football with his Air Raid offense. Of course, this offense was not conceived in a flash of inspiration: it was the product of more than a decade’s worth of imitating the best passing offenses in the country. Early in his career, instead of starting from scratch, he realized he could build on top of existing concepts. He mastered the formations and plays that other coaches used, making adjustments and experimenting as he went. He subtracted the extraneous, shrinking phonebook-sized playbooks down to just a few plays. He chose depth over variety. He meshed plays together. He added his own theories and ideas, extending the line to compose the Air Raid offense and change the way football is played. “If we’re free from the burden of trying to be completely original,” Austin Kleon said, “we can stop trying to make something out of nothing, and we can embrace influence instead of running away from it.”

Find Wisdom Everywhere

One of my favorite things about Stoicism is that it has no immutable laws. The Stoics encouraged new ideas to be built on top of existing ones. They gladly welcomed any worthy idea, regardless of the source. “I’ll never be ashamed,” Seneca said, “to quote a bad writer with a good saying.” In fact, Seneca used quotes from Epicurus, the founder of a rival school. Marcus Aurelius would quote various philosophers throughout Meditations, rephrasing and reworking lines to push the ideas deeper into his psyche.

Sing the best songs, practice the best plays, contemplate the best ideas. Over and over and over. Then make them your own.

What does not yet exist

Author Steven Pressfield said most people pay attention to their careers, communities, finances, etc. “Not me,” he says. “I put my attention on the unknown or as-yet-unrevealed content of whatever book or story I’m working on.” If you’re in the creative or entrepreneurial realm, “what you’re interested in is something that doesn’t exist yet. Or, perhaps more accurately, something that does exist but whose contours have not yet revealed themselves.”

The idea of what doesn’t yet exist, which is this email’s theme, has shown up in recent stories I’ve read…

The Next Most Necessary Thing

On December 15, 1933, a woman named Frau V. asked Carl Jung how to best live her life. The short answer: no one can tell you. “One lives as one can,” Jung replied. If she wanted a definite answer, a definite path, she “had best join the Catholic Church, where they tell you what’s what.”

The individual path, he explained, is never prescribed. You won’t know what it is in advance. It doesn’t yet exist. All you can do, he said, is the “next most necessary thing”; put one foot in front of the other.

The next most necessary thing. That’s how you live your life, how you make your own way. That’s how you create what doesn’t yet exist.

What Could Be

Coach Hal Mumme revolutionized American football. From the beginning of his coaching career in the late 70s, Mumme was obsessed with creating the perfect pass. He traveled the country in search of information, picking the brains of forward-thinking coaches who weren’t afraid to throw the ball. He learned Bill Walsh’s West Coast offense. He studied Glen “Tiger” Ellison’s radical yet brilliant run-and-shoot offense, which involved spreading the field and forcing the defense to cover more ground. He learned Darrel “Mouse” Davis’s pass-heavy, option-friendly improvement to the run-and-shoot. He studied the films of BYU—one of America’s greatest passing offenses in 1985. From the Canadian Football League’s second-winningest coach, Don Matthews, he learned the power of the 2-minute drill. (Mumme would sometimes run the 2-minute drill throughout an entire game, demolishing stronger and faster teams in the process). 

What pushed him to keep learning, experimenting, synthesizing, and creating was the feeling that there was still something missing. He had a vague notion that these ideas could be made into a repeatable system. He couldn’t have known it at the time, but by keeping his attention on what could be, on what did not yet exist, he would eventually develop this system, the legendary Air Raid offense (parts of which are used today by everyone from the Bowling Green State University Falcons to the San Francisco 49ers), and forever change the way football is played.

The Art of Living

Marcus Aurelius says to himself, and us, “You have proof in the extent of your wanderings that you never found the art of living anywhere—not in logic, nor in wealth, fame, or in any indulgence.” Where, then, is the good life found? In actions based on the principles of justice, self-control, courage, and wisdom.

Like Jung, Marcus said life’s meaning is found in action. It’s not found by asking a wise person, or by reading thousands of books. It’s certainly not found in idle pondering. The meaning of life, as Viktor Frankl said, is not our question to ask. Life is asking us the question, at every moment.

We answer through our actions. We answer by doing the next most necessary thing, putting one foot in front of the other, imagining what’s possible, and moving closer to what could be.

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