The Daily Stoic - 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday

The Daily Stoic - 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday

Our Wise Guide: Stoicism, unlike many other philosophies, is intended to help you live life. It’s not concerned with abstract, esoteric problems. Rather, it seeks to help you answer that eternal question: How should you live? What do you need to do to live a good life? Ryan Holiday’s The Daily Stoic is a guide to developing these qualities in yourself. The Stoics taught that virtue was the highest good in life – and that, to be virtuous, we must foster in ourselves virtue’s four subtypes: courage, wisdom, moderation, and justice.

1. Examine both yourself and the company you keep.
For the Stoics, philosophy begins with self-examination. The great Stoic teacher of the second century CE, Epictetus, said we become philosophers the moment we first examine our preconceived notions, and ask questions about our emotions, beliefs, and even the words we use each day. This is the way that we begin to investigate our own mind.

Self-examination is no easy task, of course. Ego and self-deception will try to thwart your quest for self-knowledge, assuring you that you already know yourself. But remember the words of Epictetus: “It is impossible for a man to learn what he thinks he already knows.” So, as you examine yourself, stay humble, stay open and receptive, like a good student.

What you see might be hard to look at: weaknesses, bad habits, pride and self-regard. Push through the pain. Keep looking. It’s important to take stock of everything, even if it’s uncomfortable. If you don’t take an honest look at your less lovely qualities, you’ll never be able to work toward changing them.

In addition to self-reflection, it’s also important to be aware of those around you.

The people you spend your time with will influence the kind of person you become. If you’re around people who push you to be better, you’ll improve. Of course, the opposite is also true.

The Roman playwright and philosopher Seneca, who was a generation older than Epictetus, advised that we should each keep someone in mind whom we respect and admire. The mere thought that someone is witnessing and sympathetically judging our behavior, Seneca said, will help us.

Point is: if you get to know yourself and others better, you’ll be able to see your actions in a clearer light. And this clarity will help you choose actions that are courageous, wise, moderate, and just.

2. Tips for maintaining focus.
It’s become a cliché: we live in a time defined by distractions. The news cycle. The internet. Our devices. Social media. We’re pulled in a million different directions by a million different things. But distractions, though they may have become more extreme, are nothing new.

Marcus Aurelius, the Roman Emperor and Stoic thinker, had a method for eliminating distraction. He advised that we approach each task as if it were our last. Whatever you’re doing, pretend it’s your last act, the final thing you’ll do before death – and try to take this mental exercise seriously. The effects can be pretty incredible, not only erasing distraction but increasing quality. After all, this is your last act, so you better make it count.

Another good technique for maintaining focus is recognizing and accepting that some things are simply beyond your control.

For the Stoics, there’s only one thing you can control: your mind. What about your body, you ask? Well, it’s going to get sick or injured whether you like it or not. You can’t control that. You can, however, control your thoughts. So ignore everything that’s not your mind, everything that’s not in your control.

The benefits of this are twofold: it’ll sharpen your focus and lift the burden of responsibility. Remember: all you need to worry about is your mind, as well as the choices and actions that are the consequences of its reasoning.

Practically speaking, you can use this knowledge to create a useful daily routine.

In the morning, take a minute to remind yourself of what you can and cannot control – and only focus on the former.

At midday, remind yourself that the only ability you really possess is the capacity to make choices.

And before you turn in for the night, consider how much is outside of your control. You can sleep easy knowing that, as Epictetus taught, those matters can be left to fortune.

3. You can’t control situations, but you can control how you react to them.
Another lesson from Epictetus: if the way you’re approaching a situation is not bringing the desired results, you might be using the wrong handle. In the Enchiridion, Epictetus teaches that every situation has two metaphorical “handles,” that is, two ways you can approach it. One can be used to “carry” it, while the other can’t.

Epictetus gives an example. Imagine that your brother has done you wrong. There are two handles. One is your brother’s wrongdoing – but if you grab this handle, you’ll never successfully “lift” the situation. The other handle is the fact that this is your brother, that you were raised together, that you love each other. That is the handle to use.

Let’s look at another example, the example of the journalist William Seabrook.

In 1933, Seabrook sought treatment for his alcoholism by committing himself to an insane asylum. At the time, these were the only treatment centers for addiction.

At first, Seabrook approached the situation as an addict. He rebelled. He resisted treatment. He made himself into a pariah. But then, on the brink of being expelled for his continued issues and bad behavior, Epictetus’s metaphor of the two handles crossed his mind – and jolted him into action. Up until that point, he realized, he’d been holding the wrong handle: the handle of addiction, not the handle of recovery.

So he took hold of the other handle. He embraced the process and began to enjoy not only the asylum but even sobriety. By opening himself up to a new approach, by taking hold of a different handle, he reached his desired goal.

Seabrook’s story is inspirational and impressive – and you might not get the same life-changing results. But if one handle doesn’t work, there’s no harm in trying the other one.

4. By being alert about our biases, we can bring more clarity to our thoughts.
Stoics know that the vast majority of us aren’t nearly as intelligent as we’d have ourselves think. But we can improve our intelligence. How? By remaining humble and identifying the flaws in our thinking.

You can start by testing your thinking for biases.

The mind has a nifty ability to make split-second decisions based on past experiences. Like, you hear an angry dog barking behind you and, before you know it, you’ve leapt into the branches of a nearby tree. That’s helpful and good. But, as Malcolm Gladwell points out in his book ''Blink'', this ability also has a downside: it’s just as easy for us to self-affirm our prejudices at the same lightning speed. For instance, you meet a total stranger at a party who just so happens to look exactly like your high school arch nemesis, and you find yourself being rude to this blameless stranger.

It’s not always easy, but, before you act, try to pause and consider what assumptions and prejudices you’re bringing to the table. Ask yourself questions like, What could I have overlooked here? or Is it possible I’m wrong about this?

Just a little bit of self-assessment can go a long way toward avoiding embarrassing mistakes.

The same principle holds true when it comes to evaluating patterns of behavior.

Marcus Aurelius wrote that we should look for cause and effect in our thoughts and actions, and try to understand which kinds of actions result from particular prejudices.

Another way to identify flaws in thinking is to stay alert to an all-too-human tendency: automatically and involuntarily adding interpretation to what you observe.

Seventeenth-century samurai swordsman and philosopher Musashi had some choice Stoic words for this impulse – and he wasn’t even formally a Stoic! According to Musashi, a person can look at something with an observing eye or a perceiving eye. There’s a big difference between the two.

The observing eye sees things for what they truly are. In contrast, the perceiving eye imbues things with meaning. The perceiving eye tends to add its own spin and prejudice to things – and this can trouble, causing you to create problems where there are none or treat a complete stranger like a high school enemy.

5. Stoicism helps us live life action by action, one decision at a time.
Each day, every day, we’re faced with a multitude of choices and possibilities, from the mundane (Which TV shows to watch? Which restaurant to eat at?) to the momentous (Which partner to choose? How to balance your personal needs with your obligations to others?).

All this choice can be overwhelming, paralyzing. One way to overcome decision-paralysis is to conduct a little thought experiment. Here it is:

Try imagining the person that you’d like to be. Then, appraise your actions. Are you doing things that the person you’d like to be would do? Take this experiment seriously. Imagine your best self, your most virtuous self. What would you need to do to be that person?

Once you’ve mapped out some actions, don’t procrastinate. Act now.

Marcus Aurelius wrote that if you want to change something about yourself, the best day for action is always today.

Think of yourself like an archer taking aim at a target. You’re only going to hit a target that you aim at, and you’ll certainly only hit something if you actually let go of that arrow!

Ultimately, then, procrastination is best thought of as a form of resistance that blocks you from achieving your goal. So how can you lower that resistance?

Well, one Stoic-approved approach is to enjoy the process. Definitely set goals. Definitely take aim at that target – becoming your best self. But, once you’ve done this, don’t fixate on what you’re trying to achieve. Enjoy the journey.

Epictetus loved reminding his students that there’s no such thing as the perfect Stoic. Living a perfectly virtuous life, always acting courageously, wisely, moderately, justly – that’s simply impossible. But the ideal of the perfect Stoic is still important. It’s what all Stoics should strive to be.

But life isn’t about big, earth-shaking epiphanies. You won’t wake up one day and be your perfect self, just as no Stoic will ever be the perfect Stoic. All you can do is work toward perfection.

So savor the process. Enjoy the work. If you do that, you’ll be on your way to getting as close to perfection as anyone else.

6. Stoics manage expectations when dealing with problems and setbacks.
Making plans, setting goals, having ambitions – it’s all important. But plans can only get you so far. After all, no plan can take into account all the obstacles that might arise on the path to its completion. Which is why, to navigate life most effectively, we need to find ways to deal with obstacles.

Stoics know this. Instead of obsessively planning ahead, trying to factor in every possible complication, Stoics foster creativity, independence, and inventiveness. This makes them flexible, as well as resilient in the face of changing circumstances. In short: prepared to overcome any challenge that life throws in their path.

Though overcome is maybe the wrong word. Stoics train themselves to turn obstacles to their advantage, to use obstacles as opportunities.

One way they achieve this is by having what the authors call a reverse clause – in other words, a backup option. So, for instance, what do you do if your computer erases your work? No problem. It’s an opportunity to start fresh on a new and improved version. You get stuck in traffic? Fine. It’s an opportunity to finish your audio book.

Having a reverse clause for every situation means your progress will never be halted. Each obstacle will become an opportunity to make progress elsewhere.

This is such an important skill that Ryan Holiday wrote an entire book about it – The Obstacle is the Way. So keep the words of Marcus Aurelius fresh in your mind: “The impediment to action advances action. What stands in the way becomes the way.”

7. Aspire to virtuousness in all you do.
All Stoics aspire to virtuousness. According to the Stoics, virtue is the highest purpose one can commit to. And, as you know, virtue itself is a composite concept made up of courage, wisdom, moderation, and justice.

Aspiring to virtuousness is beneficial because it will help you cut through all of life's confusions. An example: let’s say your sole goal in life is to make money. The issue with this goal is that, first off, you’ll never have enough and, second, you might compromise your character, committing atrocious deeds in pursuit of self-enrichment.

Virtue is different. If you truly pursue it, truly striving to act courageously, wisely, moderately, and justly, you won’t sacrifice your morals on the altar of greed. You may make plenty of money in your life. Why not? But that money won’t be the be-all and end-all of your life, and it certainly won’t be ill-earned.

To pursue virtuousness, though, you have to be entirely self-committed: no one’s going to make you do it. As Seneca wrote in his Moral Letters, “Every noble deed is voluntary.”

Look at Marcus Aurelius: as emperor, his political, personal, legal, and military responsibilities were massive, and he must have been overwhelmed at times. No one was ordering him to act virtuously – but he did. He committed fully, always aspiring to “good character, good intentions, and good actions.”

For Marcus, for many other Stoic thinkers, this entailed helping others.

As Marcus Aurelius put it in his Meditations, working with others is what “you’ve been made by nature for.” Each of us has a stake in making the world a better place – and the best way to do that is to help one another.

8. Stoics are focused on results, so they’re pragmatic in their actions.
Philosophy sometimes gets a bad rap as an ivory tower occupation. But Stoic thinking is different. It’s about achieving results, and not getting sidetracked on the way there.

That’s why the special quality of Stoics is getting things done no matter the circumstances.

Many artists find themselves stuck in their work. And many of them chase inspiration by moving to new locations or seeking new experiences. Still, they often find themselves blocked.

That’s because, ultimately, if you’re looking for the perfect set of working conditions, then you’re just deceiving yourself. In reality, it makes no difference where you are. You’re just going to have to get down to it and press on.

The same principle goes for practicing Stoicism itself. It’s for real-world situations – there’s certainly no need to enter a monastery to live stoically. You can do it here, now, wherever you are.

Another truth that Stoicism recognizes is that while the things we do might be imperfect, this doesn’t mean we shouldn’t try at all. This kind of “all-or-nothing” thinking can prevent you from making any progress.

So don’t let perfection be the enemy of the good. It’s better to try and to fall short than not to try at all.

In his book Rules for Radicals, community organizer Saul Alinsky argued that we shouldn’t let our idealism limit us in setting our goals. According to Alinsky, an organizer has to accept that the world is as it is before she tries to change it. Accepting things as they really are doesn’t weaken the desire for change; in fact, it makes the effort to bring it about more effective.

9. Stoics rely on themselves, remaining resilient despite changing circumstances.
Stoics believe that no matter what happens to us, we always remain in control of who we are. They even came up with a metaphor for this. We each possess an Inner Citadel, which remains impregnable, completely in our control, no matter what we may endure physically.

The Stoics said that this Citadel houses the soul. But whether you believe in souls or not, the metaphor is useful. Remember: this Citadel is impervious to external threats. But it can be threatened from within.

In other words, though your Citadel can’t be damaged by rain and lightning, it can be damaged by how you react to bad weather. Though a grievous accident can’t harm it, it can be harmed by how you react to that accident.

Take the example of Cato the Younger. He liked to be prepared for any eventuality that might befall him. For instance, even though he could afford fancy clothes, he chose never to wear a hat regardless of the weather, so that he’d always be prepared to withstand the elements. He walked around barefoot, so that, if ever deprived of footwear, he’d be unfazed.

After all, to a Stoic, misfortune is just another opportunity to become stronger. In On Providence, Seneca even claims that someone who has never known difficulty is unlucky; it shows he’s never been tested, so there’s no way he’ll know his true potential.

There’s a second consequence to the Inner Citadel: Stoics know that only they have power over their own minds, which makes them very resilient.

US pilot and Navy vice admiral James Stockdale was living proof of this. When his plane was shot down over Vietnam, he knew that incredible hardships would follow. But, as his plane went down, he thought of the teachings of Epictetus and knew he could hold out.

Stockdale spent the next seven-and-a-half years as a prisoner of war, during which he was brutally tortured by his captors. But he never sought solace in unrealistic expectations of sudden liberation, and he never allowed the experience to change who he was.

Stockdale knew that staying true to himself was his best hope of resistance. Indeed, he was so committed to this philosophy that he once deliberately injured himself so that he wouldn't be forced by his captors to appear in a propaganda video.

As a Stoic and a student of Epictetus – who, remember, was enslaved until he was 30 years old – Stockdale knew that though there was nothing he could change about his situation, he could always control his reaction to it.

Fortitude in difficult circumstances is an admirable skill, but as we’ll examine now, you don’t always have to go it alone.

10. Stoics understand the interconnectedness of all things and commit themselves to the right action.
In Antiquity, violence and cruelty were all-pervasive. Animals and people were killed for entertainment in amphitheaters across the Roman Empire, while conquered peoples were routinely enslaved. It was hardly an atmosphere that encouraged positive feelings of camaraderie.

What’s fascinating is that Stoicism – which reached philosophical maturity at that time – regarded the workings of all people and creatures as connected.

The Stoics called this interconnectedness sympatheia. It helped them envisage everything as part of a larger whole.

In his Meditations, Marcus Aurelius described how everything in the universe was interconnected. He even explained through an analogy how people should be imagined as bees living in the same hive: what is bad for the beehive will ultimately be bad for the bees. To put it the other way around, anything that isn’t harmful to the community can’t ultimately harm the individual.

Because a wise person understands that the good of the many is always the highest priority, this means that all impulses and actions should be directed toward that aim.

Doing right by the community is all well and good in theory, but right action does sometimes require personal motivation.

After all, it can be tempting to act selfishly, but it doesn’t usually end up doing you any good in the long run.

For instance, we might occasionally convince ourselves that enacting a spot of revenge will do us a world of good. But actually losing control like that just makes us sick. As a rather disturbing example, vomit is often found at crime scenes for precisely this reason.

And what’s true of crime also holds for lying and cheating. It just makes us feel worse for acting in a way we know is unethical.

Here’s a practical exercise that will make acting correctly easier. Before doing anything, ask yourself once again, "Is this what the person I’d like to be would do?" Think about the standards you’ve set for yourself and use those to guide you in the present moment.

11. For Stoics, fate is not a source of fear, but instead motivates them.
It’s a common tendency to think of hope as good, and fear as bad. But Stoics are skeptical of both. After all, both hope and fear involve attaching value to future events which are, by definition, out of our control.

So instead of focusing on wishes and worries, Stoics prefer amor fati, “a love of fate.” In other words, they go a step further than throwing up their hands and saying “what will be, will be.” They embrace fate, even if events don’t play out in their favor.

Rather than pointlessly wishing they could change the circumstances to fit their desires, Stoics instead adapt their desires to the situation. This is the Stoics’ art of acquiescence.

It’s a clever strategy. Stoics learn to accept events and take responsibility for their own lives.

However, it’s important to note that acceptance isn’t shorthand for passivity.

Let’s look at former US President Franklin D. Roosevelt. He had craved and worked toward the office of the presidency his entire life. But suddenly, at the age of 39, he was diagnosed with polio.

FDR knew that there was nothing that he could do about the disease, but he recognized his reaction to it was entirely his choice. He therefore decided to calmly accept the situation, while refusing to see himself as a victim. The rest is history: FDR went on to be elected to the presidency four times.

Another good example is the civil rights leader Malcolm X. He was incarcerated early in life, but instead of fuming pointlessly in his cell, he chose to use his time wisely. By the time of his release, he was self-educated, religiously enlightened, and highly motivated – all character traits that served him well in the struggle for civil rights.

Just think of all that energy you could save by not wishing for the impossible. Success is entirely achievable if you invest that energy, and work with the actual situation as it stands before you.

12. Stoics do not fear death – they accept and embrace its power.
The once mighty Roman Empire fell in the West after 500 years. The longest human lifespan recorded is just 122 years.

Everything and everyone must eventually come to an end. That’s why Stoicism teaches us to accept death. And to use it as a motivator to live life well.

Marcus Aurelius wrote that we should live every day as though it’s our last. He didn’t mean that we should descend into a frenzy of hedonistic indulgence. He meant we should live bravely, without apathy, much as we should approach our every deed as though it were our last. Live as though you’ll have to look back on the day’s acts from your deathbed. Live in such a way that you’d look back and be content.

Of course, the thought of death is frightening. We can’t know what awaits us. But the Stoics recognize an important feature of death: if it really is the end of everything, there’s nothing to fear. Death brings with it the end of worry, pain and, of course, death itself.

In fact, Seneca went so far as to admonish his friends and family when they begged his executioners to spare his life. He scolded them for forgetting their philosophical training. As far as he was concerned, they should have been ready to accept death, just as he was.

“To philosophize,” Cicero argued, “is to learn how to die.” Meaning, we can use philosophy to make the most of our time.

While it’s interesting to meditate on the wisdom of philosophers and life’s big questions, to the Stoics, philosophy serves a practical purpose. It’s a tool that you must use every day to carefully shape your own life – a life that you’ll be happy with when it finally comes to an end.

Final summary
Stoicism is above all a practical philosophy. Instead of being just an abstract framework for cerebral rumination, it provides a set of guiding principles that can help you make better choices in life. Apply Stoicism successfully and you’ll find yourself not just believing in your own abilities; through determination and self-motivation you’ll be able to improve yourself and society as a whole.

Actionable advice: Don’t look for happiness in external things.

There’s nothing wrong with appreciating fine clothes or a square meal. But the more we let our happiness depend on external rewards, the less free we become. So the next time you’re looking for “likes” on social media or trying to boost your mood with a fancy purchase, ask yourself what meaningful action you could be taking instead. The effects will last a lot longer.

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