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.