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.

10 things I learned, found interesting, or used this month

1. If everything seems under control, you’re not going fast enough.

2. 10 in, 1 out.
In order to have 1 good idea, you need to consume 10. 

3. Let it float on by. I’ve been thinking a lot lately about discarding thoughts: if a toxic thought pops into my head, I can immediately discard it. When I told my wife about this, she pointed out that in order to discard something, I first had to possess it. It’s better, she said, to watch the thought from a distance, and let it float on by.

4. The 40% Rule. Jesse Itzler learned the 40% Rule from a Navy SEAL he lived with. “He would say that when your mind is telling you you’re done, you’re really only 40 percent done. And he had a motto: If it doesn’t suck, we don’t do it.”

5. Bore yourself into good ideas. The philosopher Leo Tolstoy said that when our minds are calm, useful thoughts appear. Austin Kleon, in his classic book on creativity, talks about his love for ironing shirts. “It’s so boring. I almost always get good ideas.”

6. When reading a biography, it’s more important to understand the person’s motives, rather than the events.

7. Clean up your desk. I loved this chapter in Discipline is Destiny. We waste so much time scrolling, shuffling, and moving things around just to do simple tasks. “A person who puts up with needless friction will eventually be worn down.” I consider myself to be fairly tidy but I used some of the ideas from the book this month to tidy up even more: I donated a grocery bag of pens and pencils to a local school. I moved extra highlighters, Sharpies, and anything else I rarely use, to the closet. Finally, I cleaned up my writing desk (separate from my work desk), keeping only the bare minimum: a computer, lamp, pen, pencil, planner, and notecards. Another cool idea: use a table as an office desk. Things are more likely to get done when there are no drawers to shove them into.

8. Be content to be thought foolish. This is one of my favorite quotes from Epictetus: “If you wish to improve, be content to be thought foolish or stupid.” Who cares if you don’t know who won last night’s game? Or that you haven’t heard the latest scandal everyone’s talking about? If you wish to acquire wisdom, Epictetus said, you have to be okay with appearing ignorant. Further, you don’t have to have an opinion. Let other people talk and gossip and argue. Your mind will be clear and tranquil, and you’ll have more energy for your own improvement, and your own work.

9. Everyone is doing their best with what they’ve been given. Socrates said that no one does wrong on purpose.The logic, of course, is that people who do wrong are harming themselves, and since people don’t harm themselves on purpose, they don’t do wrong on purpose. I really liked how Ryan Holiday wrote about it: People are doing the best they can with what they’ve been given. They weren’t given your brain, your experiences, your circumstances, your influences. The friend who repeatedly makes destructive choices, the sister who just can’t seem to get it together—surely they wouldn’t act this way if they knew the harm they were causing themselves. They wouldn’t act this way if they could help it. They’re doing their best, as we all are. If they’re open to advice, give it. If they’re not, let them be. Focus on the good in them. There are things that they’re better at than you. Learn from them. Most of all, love them. And be grateful with all your heart for the opportunity to share this beautiful, brief existence with them.

10. Notable books I read this month:How to Live: Or a Life of Montaigne in One Question and Twenty Attempts at an Answer by Sarah Bakewell, Discipline is Destiny by Ryan Holiday, First We Read, Then We Write by Robert D. Richardson, The Perfect Pass by S.C. Gwynne, How To Be a Bad Emperor by Suetonius

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.

Mimetic desire

Early in his career, professor and philosopher René Girard was asked to teach literature. For the first time, he read classic novels by authors like Dostoyevsky, Proust, and Flaubert. During his readings, Luke Burgis tells us, he noticed a pattern: none of the novels were plot-driven or character-driven; they were desire-driven. The object of the characters’ desires? Other characters’ desires. We are hardwired to imitate. Our desires, he realized, are mimetic.

Models of desire are all around us, which is why I’m using mimesis as this week’s theme…

To Be or To Do

The best American Fighter Pilot in history, John Boyd, first gave his famous “To Be or To Do” speech to the young Captain Raymond Leopold: 

“Tiger, one day you will come to a fork in the road, and you’re going to have to make a decision about which direction you want to go.” He raised his hand and pointed. “If you go that way you can be somebody . . . you will be a member of the club and you will get promoted and you will get good assignments.” Then Boyd raised his other hand and pointed another direction. “Or you can go that way and you can do something—something for your country and for your Air Force and for yourself . . . . you may not get promoted . . . .  and you certainly will not be a favorite of your superior. But you won’t have to compromise yourself. You will be true to your friends and to yourself. And your work might make a difference.”

To be somebody, or do something. To work for a title, or for a cause. To want what other people want, or what you want. To think mimetically, or purposefully.

Torches of Freedom

In 1929, the president of the American Tobacco Company asked public relations expert Edward Bernays to help rid the negative stigma around women smoking in public. Bernays agreed and decided on the perfect time and place: the Easter Day parade in New York City. The parade was a way for high-society New Yorkers to sashay down Fifth Ave, showing off for the feverish media and lower-class onlookers. Bernays convinced a few of the parade’s influential women to smoke while they strutted down the street. He made sure that the photographers and journalists covering the event referred to the women’s cigarettes as “torches of freedom”. It worked. Women began lighting up in public, a celebration of liberty. Within a year, sales of Lucky Stripe tripled.

Peter Thiel’s $500,000 Bet

Our tendency to model behavior is what makes Facebook so influential: it’s full of billions of models of desire. It’s not celebrities or pro athletes that influence us most, it’s the people who look like us. When asked about his $500,000 Facebook investment that earned him $1 billion, Peter Thiel told Luke Burgis, “I bet on mimesis”. 

Find Yourself a Cato

Roughly two millennia before Girard put a name to it, Epictetus saw mimetic desire firsthand. As a slave in Nero’s court, he witnessed the endless cycle of competition and conflict. He watched as people fought and conspired over power, money, and fame—things they wanted because other people wanted them.

Five hundred years before Epictetus, the Buddha recognized our proclivity to mimic what we see. We’re on the constant lookout for change, he said, which is why desires and cravings seize us from moment to moment. As Karen Armstrong writes, the Buddha understood that “we are consumed and distracted by the compulsion to become something different.” 

We’re inclined to become something different, but we’re also inclined to become something better. That’s why we have ambition, why we want to grow, why we work so hard: to become who we’re capable of becoming. And the best place to start? Choosing a model worth following, a person whose values align with ours, and whose example teaches and challenges us.

Seneca advises us to “choose ourselves a Cato.” Choose someone whose high standards encourage us to raise our own.

“If, at any moment, you are unable to name a great man who is, or has recently been, having an influence on your conduct,” Ernest Dimnet said, “you will be passing the verdict: ORDINARY on the quality of your own thought and existence.”

Find a model whose greatness inspires your own.

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