Read Stoicism

Your first philosophers: Marcus Aurelius, Epictetus, Seneca, and one strange new face. Why the first books people read about Stoicism should be by one of these guys.

On Stoicism

Graduation season is coming up, and with it, some great advice will be handed down via the time-honored tradition of commencement addresses. If I tapped to share my best advice, I'd want to pick something pithy enough to stick, but important enough to share — my personal version of Wear Sunscreen.

Here's the best advice I could give on becoming more resilient, happier, and more successful: Read Stoicism.

A quick note before we get started — I don’t have quite the talent for brevity that Mary Schmich had when she penned “wear sunscreen.” So this essay may be on the long side. I apologize in advance. If you'd prefer to have it emailed to you so you can read it later, click here.

In the last four years, I’ve learned a lot about mortality. I’ve faced harder challenges than I ever expected to personally experience—at least not at my age.

Despite those challenges, I am happier than I ever have been. I spend most days in good spirits—oddly enough, even thankful for the challenges that I’ve overcome.

I've created this happy outlook primarily through reading the Stoics, reflecting on what they've said, and trying to apply those lessons to my life.

Becoming a Stoic…

"If you’re going through hell, keep going." -Winston Churchill

Stoic ideas give me encouragement to keep fighting through hard challenges, even when I’d rather give up.

My first introduction to Stoicism came from reading Seneca’s Letters from a Stoic. It immediately helped me solve a problem that I was facing.

I was shocked -- I had always learned about philosophy as kind of an esoteric, academic thing. Certainly not something that was actually helpful. I was hooked, I bought more books.

Today, I practice Stoicism as a type of life hack. It makes me happier with my current life and it pushes me to higher levels of accomplishment. Two sometimes competing concepts, both of which are important to me.

Letters from a Stoic is brilliant, but it was so full of anachronisms that it was hard to read. Sometimes I devoted so much time to deciphering what Seneca is saying, that I wasn’t able to appreciate the advice he was giving. 

Nevertheless, I highlighted almost every page of that book. Today, when a close friend faces either a large challenge or opportunity, I often buy them a copy of Letters from a Stoic.

Until now. Today, a new book has replaced Letters from a Stoic as my go-to recommended introduction to Stoicism. The Obstacle is the Way, written by Ryan Holiday. The book is a far more approachable place to start.

Reading this book reminded me of first learning about Stoicism—and it inspired me to write this post and share my best advice with you. I’ve suggested that many close friends look into Stoicism. If you’re feeling unsatisfied or unmotivated, I’d suggest that you look into it too. 

Of course, Stoicism is not a panacea. There are many paths to similar ideas. Ryan Holiday, the author of the book I recommend below, even points out that the title of his book: “The Obstacle is the Way”, is remarkably similar to a Zen proverb: “The Obstacle is the Path.”

Stoicism uniquely differs from other philosophies in it’s use of plain language and ideas. It’s easy to understand what the Stoics are trying to say (once you get past the anachronisms).

The writings of Stoic philosophers offer pragmatic advice, uncomplicated by intricate language or presentation, that is both useful and immediately applicable.

Stoicism has one of the easiest on-ramps I’ve seen in any type of personal development. You don’t have to be more flexible to get started, you don’t have to fundamentally change how your brain processes ideas, and you don’t have to parse dense and confusing texts.¹

It’s even easier with The Obstacle is the Way. The book uses modern language and examples that make the concepts much easier to understand. It’s a far easier read, but still contains the core insights of Stoicism. It takes what was already a shorter on-ramp, and makes it even more approachable. That said — learning the principles is easy, the challenge is in applying the knowledge, not in consuming it.2 

Who can get value from Stoicism?

Anyone can apply Stoicism to their life. The challenges that the Stoic authors tried to solve include common challenges that we all face today.

Here are some examples of challenges that friends of mine have faced where a Stoic outlook helped them tackle the issue:

  1. How to build a stable career in uncertain times
  2. How to build and retain strong friendships
  3. How to react when others judge you or hurt you
  4. How to deal with the death of a loved one
  5. How to live a happier life

In an interview I did with Ryan (see below), he noted that Stoicism commonly sees a resurgence during uncertain times. As we undergo one of the biggest cultural and economic shifts since the industrial revolution, it’s not hard to see how everyone can get increased value from the Stoics.

For particularly ambitious people, Stoicism is even more useful. It helps you prioritize properly, develop a penchant for action, and motivate yourself through dark times. It helps you develop as a leader. In his book, Ryan shows just how many of history’s greatest leaders embodied stoic principles:

  1. John D. Rockefeller
  2. George Washington
  3. Arnold Schwarzenegger
  4. Thomas Edison
  5. Ulysses S. Grant
  6. Margaret Thatcher
  7. Teddy Roosevelt
  8. Steve Jobs
  9. Dwight Eisenhower
  10. the list goes on…

The Obstacle is the Way is the best introduction to Stoicism that I’ve found. Despite getting a free digital copy to review, I already purchased two additional copies knowing that I’ll want to give them to friends. 

I suspect Ryan’s book will improve many lives3, just as the first time I read Seneca improved mine. If you're a new grad, and your commencement speaker was lackluster, so you're reading this looking for my best advice, here it is: read that book.

If you are already happy and effective, feel free to ignore or engage only academically with Stoicism, you clearly have a system that works for you. If you feel like you need some help improving, I’d suggest reading the Stoics. You could start with Ryan’s bookSeneca, or even just the right reddit thread.

I’ve included a list of resources4 at the bottom of this essay which can be a great place to start. If you don’t trust my word on why this study might be worth your time, I think Henry Fielding sums it up quite eloquently (emphasis mine):

If a man, for instance, should be overloaded with prosperity or adversity (both of which cases are liable to happen to us), who is there so very wise, or so very foolish, that, if he were a master of Seneca and Plutarch, could not find great matter of comfort and utility from their doctrines?


An interview with the author

After reading the book, I sat down to review my notes (over 150 highlights, notes, quotes, and links). From that review, I wrote down a few questions that I thought would make a useful compendium to this essay—something that would summarize Stoicism and the book from Ryan’s point of view.

Ryan was gracious enough to answer them in depth and with examples. 

Tyler: Let’s start with a simple definition, what is Stoicism?

Ryan: Stoicism is a philosophy that became popular with the elite of the Greco-Roman empire. Unlike other more theoretical schools of philosophy, Stoicism is a set of practical philosophical principles that are meant to be practiced in your life. The Ancient Stoics like Seneca and Marcus Aurelius wrote personal exhortations to themselves, never intending their writing for publication, so they lack the puffing and rationalization that comes from presenting yourself to an audience. It’s really a system designed to direct our actions and thoughts in an inherently unpredictable world. 

Tyler: How did you discover stoicism? What made you want to apply it to your daily life?

Ryan: I was lucky enough to be introduced to Stoicism by Dr. Drew of Loveline fame when I was nineteen. I walked up to him after conference for college journalists and asked him what he was reading. He recommended the great Stoic Epictetus. I went back to my hotel and ordered that and Marcus Aurelius’ Meditations and Meditations arrived first. 

I was going through a tough break up at the time and wasn’t sleeping well. I was so blown away that writing like this existed, ignoring the fact that it was written almost two thousand years ago. From reading Meditations I was able to see that so much of life is out of our control and that so much of our action, or lack thereof, are predicated on our perceptions of these uncontrollable events. So it totally shifted my mindset.

Tyler: When was the first time that you realized adhering to Stoic principles gave you an advantage in your daily life?

Ryan: Shortly after I was introduced to Stoicism, I took a hard left turn and dropped out of college at 19. I moved to LA and basically had to teach myself the ropes in some pretty high stress jobs. Throughout all this I kept revisiting Meditations to help me weather the storm and keep myself grounded.

Tyler: In the book, you give examples of famous historical figures who were Stoics. Who are some of those successful people who applied Stoicism? How did Stoicism give them an advantage?

Ryan: One famous Stoic I talk about is James Stockdale, who was in the same prison camp as John McCain was in Vietnam. When he was shot out of his plane over Vietnam, he said to himself, “I am leaving the world of technology and entering the world of Epictetus,” which is a pretty crazy reaction. I mean, he knew he was going to be captured behind enemy lines and he used Stoicism to give him solace during what had to be a terrifying experience.

For seven years he was able to provide leadership and support and direction to his fellow prisoners, even attempting to commit suicide at one point to send a message to the guards. And going into it all he reminded himself that Stoicism would help him through it.

Tyler: You talk a lot about discipline, and having a penchant for action. How important is it to optimize for action over contemplation? What role should contemplation play in your day-to-day life?

Ryan: In the book I talk about taking deliberate action. I don’t think there’s anything wrong with deliberating over choices you have and examining all your options. Reckless action is often just as bad as not taking action at all. But I think when you start contemplating you can bring on a lot of what Stoicism tries to prevent: anxiety, thinking about things you can’t control, paralysis by analysis, etc. So its important to recognize the difference here, because with contemplation I think we can get lost in our own heads.

Tyler: Every philosophy has faults - what’s the biggest problem with Stoicism?

Ryan: I think one of the problems with Stoicism is the way people interpret it. They read Seneca or Epictetus and see some of their habits as being a little to extreme and say, “Well, that’s crazy, I’m never going to do that.” 

Or they mistake being stoic, as being unemotional and negative. In my view Stoicism isn’t going to lead you astray. But if you take some of the actions or views the Stoics had too literally, I could see how people could be turned off or led astray.

Tyler: In the book, you present ancient ideas through modern examples. Why did you decide to write it this way?

Ryan: Well I recognized from the beginning that there aren’t many people looking for a book on practical philosophy. And there’s no way to improve upon the original writing of Marcus Aurelius, Epictetus, and Seneca, so I wasn’t going to try a fool’s errand. 

But from my training with Robert Greene and my research throughout the years I was able to recognize stories of great people from history who overcame tremendous adversity and were practicing these Stoic principles whether they knew it or not. Some of the chapters in the book aren’t based on any specific Stoic principle at all, but the stories and the people within them certainly embody the spirit of Stoicism. 

[Note from Tyler: I can’t praise the decision to use tangible examples from familiar people enough. This decision, more than any other, is what made this the most readable book on Stoicism I’ve encountered.]

Tyler: What is the most important idea in the book?

Ryan: I think the most important idea of the book is the Stoic maxim that the book is based on: 

“The impediment to action advances action. What stands in the way becomes the way.” 

The first section of the book is about the discipline of perception, which is essential to overcoming adversity. Instead of giving into panic, fear, and anxiety when we are faced with an obstacle, we can flip it on its head and instead look for an advantage or positive to pull from it. 

Marcus Aurelius has another great quote about this, “Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” It’s so important not to given into our basest emotions and instincts when we are hit in the mouth in life. People I write about in the book, like Thomas Edison and Amelia Earhart, were able to see things objectively, which is what allowed them to act and succeed in the face of tremendous adversity.

Tyler: What made you want to write a book this broad?

Ryan: I believe that you write the book that you have to write. And this is a book I’ve really wanted to write for a long time. Like I said before I first discover this Stoic exercise of turning obstacles upside down when I was 19 years old. Since then it’s been seared into my brain regardless of what I’ve done and I’ve always tried to think about my problems and opportunities in life through that frame.

In the years I’ve been using it, I started to notice patterns in reading and my experiences of other people doing this exact thing whether they explicitly acknowledged it or not. And I knew I had to write a book exclusively dedicated to this.

So honestly it was a topic that kind of came out of left field for me, and the book idea was beyond my skill level. But the only way to change that is to attempt something that feels impossible or out of reach, and I hope I’ve succeed with this book.

Tyler: You repeat something often in the book—that the lessons that stoicism teaches us are “simple, but not easy.” Why are they so hard? Have you found any tricks that help people with adherence to these principles?

Ryan: They’re hard because they go against a lot of our instinctual, biological reactions to stress. So part of it is kind of reprogramming your initial reactions when things go wrong. One trick that I’ve always used that has helped me a lot is printing out good advice and putting it where your work. For whatever reason, we humans need these daily reminders and it’s as simple as hanging a frame on your wall or putting a Post-It on your bathroom mirror. I’ve found that reminding myself and revisiting the principles has helped me immmensely in internalizing them.

Tyler: There seems to be a lot of increased interest in Stoicism, what is driving this rekindled popularity? 

Ryan: There seems to be a resurgence in Stoicism during uncertain or turbulent times. Often people look to it to get them through periods where there are large societal shifts that they can’t control. So I think that is part of it, with the recession, joblessness, and student loan debt that people are dealing with today. I don’t necessarily think that I’m driving the renewed interest in it, but I definitely think me being introduced to it during the recession was great timing for me.

Tyler: Are we too weak today? You quote great thinkers throughout the ages (Emerson, Churchill, etc.) who suggest that most people give up too easily. Do we suffer from that as well? Has technology made it worse or better?

Ryan: I think in some ways we have become entitled and expect certain things to go our way. Don’t get me wrong, technology has improved our lives in unimaginable ways and will continue to, but there is a dark side to it that I think we are a little reticent to talk about. 

A lot of kids of my generation expected to get a decent job coming out of college, but then the recession hit, and all of the narratives we had been told growing up weren’t the case anymore. Instead of getting angry or giving up, I think it’s important to remember that earlier generations faced much worse problems than us and had fewer safety nets at their disposal. And so we should instead double down and at least take a chance to prove ourselves instead of expecting things to return back to the way they were.

[Note from Tyler: Charlie Hoehn’s The Recession Proof Graduate is a fantastic book for new and recent grads facing this situation. If I had a younger brother or sister graduating high-school this year, I would buy them The Obstacle is the Way, The Recession Proof Graduate, a box of condoms, and write a note that said “prepare for the things you want in life, and you’ll be much more likely to get them.”]

Tyler: Some people say that Stoicism has too much emphasis on controlling your emotions — that it makes us more disciplined, but less human. What would you say to them?

Ryan: This is a common criticism of Stoicism, but I think it misses the point. Stoicism isn’t about being a negative or unfeeling person. If that’s what you get out of Stoicism I think you were probably predisposed to finding that before you studied it. It’s more of a meditative technique that transforms negative emotions into a sense of calm and perspective, instead of being paralyzed and engulfed by them.

Tyler: You say that academics have a robbed us of philosophy’s true purpose, which is helping us live better lives. Why hasn’t Stoicism hasn’t fallen into that trap?

Ryan: I don’t think Stoicism is immune from falling into that trap. I think any philosophy professor can turn the study of it into a theoretical exercise, but that isn’t want helps people in real life.

Academics have the advantage of teaching and speaking about philosophy in journals and the classroom, so they can get theoretical and the incentives of academia call for that. But for normal people living normal lives, a theoretical discussion of metaphysics or what a chair represents isn’t going to do a whole lot of good for the guy struggling to find a job. 

I think Stoicism is the most approachable and practical philosophy I’ve come across and that’s why its been so useful to me and others like Tim Ferriss who have become big proponents of it.

—- Footnotes —-


I don’t want you to think I’m discouraging yoga or meditation, in fact I practice both and have found value in both.

When you’re actually getting deep into any self-improvement method, they all require real work. If you work to apply stoic principles, you’re rewiring your brain just as much as you would to practice meditation.

The thing that I like about Stoicism is that you can get started easily, once you get going it’s just as much work as anything else that makes you better.

2: A word of warning…

My experience with reading stoic philosophers has often been similar to reading a collection of common sense.

The ideas contained inside are not complex or exceptionally novel, in fact, many of the same concepts have made it into other philosophies or religions. The Serenity prayer, for example, has always seemed to me like the perfect summation of Stoic beliefs:

Grant me the serenity to accept the things I cannot change,

The courage to change the things I can,

And wisdom to know the difference.

The challenge in Stoic philosophy isn’t in trying to understand the ideas behind the books; it’s in actually applying Stoic principles consistently to your daily life.

You won’t get there over night, I think of Stoicism as a practice—something that you improve in over time.


If you aren’t convinced that this can be helpful, and don’t want to take my word for it, or the words of historical leaders for it, here are some comments from the blog posts Ryan wrote and the Amazon reviews for his book:

I can say with personal experience that living this kind of life makes you a much, MUCH happier… healthier… wealthier and just better person all around.

I have used some of this through some really trying experiences. High anxiety situations. It worked most of the time, but needs practice like anything else.

I’ve seen it have some great impact on some of my friends. It’s empowering, realizing that you may not always have control over your surroundings or your circumstances, but you can always control yourself and how you act.

I’ve tried and been meaning to read into the stoicism books for some time, and even started a few times - but found it difficult to dig in as they weren’t very straightforward reads (not the easiest to pick up and get into for a 30 minute read).So Ryan’s book is really outstanding…

I learn important or difficult lessons best through stories and analogies. This book has great stories from history that taught me the tough lessons a lot of us need to learn about overcoming obstacles. Like Ryan says, it’s simple but it’s not easy. And that is probably the toughest lesson of them all. Also, Ulysses S. Grant was a certified badass.

The most succinct way I can put it: This book will make you better.

I’ve been extremely fortunate in my life to have many, many people who wanted to help me. They all gave great advice and a lot of that advice were in catchy little aphorisms that bothered the crap out of my stubborn self. What Ryan Holiday’s excellent work here is, is all of those spot-on aphorisms organized, researched, exemplified, and turned into actionable, practical tools.

This is not a book in a sense - this is a Swiss Army Knife for your attitude.

Devoured this book like a dragon on steroids. A self-help guide for those who hate self-help.

What can I say? It’s a super-practical book about stoicism and its many values.

4: Resources for further study



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