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The Obstacle Is the Way (Episode 45)
848 Plays1 year ago
Want to become more Stoic? Join us and other Stoics this October: Stoicism Applied by Caleb Ontiveros and Michael Tremblay on Maven
In this conversation, Michael and Caleb discuss Ryan Holiday’s book The Obstacle Is the Way. They cover the good, bad, and provocative.
Both argue that it’s practically inspiring even if philosophically shallow. Michael argues that in a real sense, it’s not a Stoic book. Caleb pushes back – a little.
(05:30) Protreptic Philosophy
(11:44) The Necessity of Popularization
(14:35) Stoicism as An Operating System
(19:00) Motivational Power
(22:01) Shallow Stoicism
(31:16) Holiday Didn't Understand Stoicism
(33:32) Muddling Through Stoic Theory
(41:38) The Cognitive Theory of Emotions
(47:03) The Spiritual Aspect of Stoicism
(48:54) 3 Disciplines
(53:43) Meditations 5 20
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Transcript
Initial Objections to 'The Obstacle is the Way'
00:00:00
Speaker
And so that's my biggest objection to it. And I think that's mostly an objection within the context of who Ryan Holiday is now, who's someone who's established himself as kind of the, the leading authority, at least in the public sphere on stoicism. And so if you know that about Ryan and you go and you read this book and you might think, well, okay, God, I've just read this book about stoicism. And I don't, I don't think you actually have is what, is what I would argue. I think you've read a book about turning obstacles into advantages.
Introduction to 'Stowe Conversations'
00:00:29
Speaker
Welcome to Stowe Conversations. In this podcast, Michael Trombley and I discuss the theory and practice of stoicism. Each week, we'll share two conversations. One between the two of us, and another will be an in-depth conversation with an expert.
Strengths and Weaknesses of the Book
00:00:46
Speaker
And in this conversation, Michael and I discuss Ryan Holiday's book, The Obstacle is the Way, the timeless art of turning trials into triumphs.
00:00:58
Speaker
This is likely the best-selling modern book on stoicism, so it demands attention. Michael and I go through what we think is good, bad, and provocative about it. In short, we both think that it is engaging and motivating, yet its stoic theory is modeled and incomplete in a way that matters for practice.
00:01:24
Speaker
We start by giving some background on the book, move into what we like about it, and then dive into our complaints and corrections. Here is our conversation.
00:01:43
Speaker
And today we're going to be talking about the book, The Obstacle is the Way, by Ryan Holiday.
Personal History with Stoicism
00:01:50
Speaker
So Ryan Holiday, probably the most popular proponent of stoicism, and The Obstacle is the Way is his first book on the philosophy.
00:02:03
Speaker
I was trying to think about when I first read it, probably 2016, 2017, sometime around there. I had heard about the Stoics before then. In undergrad, I had a class on ancient philosophy, read a little bit of Epictetus.
00:02:18
Speaker
It didn't really strike me at the time and that it wasn't later until around 2015 or so where I had read, um, Nauseam Till I'm fragile. And from there went into Marcus Aurelius Seneca and the value of the philosophy.
00:02:34
Speaker
was much more apparent to me at that time and started really diving into it and probably about a year later. So I read Ryan Holliday's book, The Obstacles Away. Before that, I read, I think he has an article online called, Stoicism 101 for Entrepreneurs, which I did like a lot of the time.
First Impressions and Book Structure
00:02:54
Speaker
That's my short history of the book. This is the second time
00:02:58
Speaker
Listening to it or reading it rather I read it the first time and the second time around I just still listen to it well while running Some motivation to keep going. This is gonna be a book review of sorts for each gonna mention what we Thought was good about the book what we thought was bad or didn't like as much and then sections points that were interesting provocative sparked thought With that all I had it off to you Michael
00:03:27
Speaker
Yeah, great. Thanks, Caleb. This is my first time reading it. I feel like I feel like you're supposed to have read some Ryan Holiday if you're into stoicism, but this is my first time ever reading a book by Ryan Holiday, you know, two weeks ago was the first time I read any of his any of his books in long form. I've read some of his blog before. This one's from 2014. So I do really think Ryan Holiday should be credited with this popularization of stoicism.
00:03:52
Speaker
There is William Irvine's A Guide to the Good Life and Sharon LaBelle's The Art of Living. And those are really the what they in the kind of the 2000s, the popular works on stoicism. And then Ryan Holiday came along with the obstacles the way and really kind of exploded it. So exploded popularity. So it's a really important piece of writing and it's many people's first introduction to stoicism. So I was really interested in digging into it.
00:04:18
Speaker
A little bit of background about the book itself for those that haven't read it, a bit of refresher for those that have read it a while ago. It's broken up into three categories. I think this is pretty similar to Ryan Holiday's other books as well. He does this. The Ego is the Enemy, another Stoicism-inspired book. And each category corresponds to one of
Inspirational Quality and Motivational Impact
00:04:35
Speaker
the three parts of Stoic.
00:04:38
Speaker
Teaching. So stoicism divides its philosophy into desire, action, and ascent. And Ryan Holiday divides the book up into these three parts that each correspond to those. So his wordings are perception, action, and will. And then each of those are broken down into sub chapters. Each of those kind of contain a lesson. Each subject chapter has a lesson and then a story made multiple stories that illustrate those points. And it's explicitly stoicism inspired, but perhaps not
00:05:08
Speaker
not hard stoicism. It's not really an explanation of the stoic philosophy so much as it is of an exploration of people or stories that have embodied that philosophy over time. Because of that, I want to focus on that part, this idea of really using stories, really focusing on anecdote to portray examples. The first thing I'm going to start with is an example of the thing that I think the book did really well, a really good part about that.
00:05:38
Speaker
One thing to explain what this book does well, I want to explain what Epictetus teaches about teaching. Epictetus was one of the big three Roman Stoics along with Marcus Aurelius and Seneca. He actually ran a school where he would teach young men about Stoicism and he taught that there's really three educational systems and these were the three that he used. One was didactic, which is where you're just teaching people things.
00:06:01
Speaker
Another was a lencic, which is this Socratic method of questioning. It's kind of like a sparring match. And people are learning by going back and forth with you. You say, well, if you believe A, then that must commit you to B. And they go, well, I don't believe B. OK, well, then you have to reject your original argument. And it's this kind of debate. And then the third style is protreptic. And the idea with protreptic, protreptic means in Greek to turn towards.
00:06:26
Speaker
And it meant to inspire people. So this third type of system is like, I'm not going to really necessarily teach you anything, but I'm going to get you fired up. I'm going to inspire you. And I think about this when Epictetus calls his students slaves or idiots.
00:06:42
Speaker
He's being pretreptic. He's like a motivational speaker. He's pumping them up to be better people. And so the first thing I want to say that Ryan Holiday, I think, does really well, or what I really liked about this book, I think it really succeeds as a pretreptic book. I think it's really inspiring. I think it's really motivating to go through and read a lot of different stories of people who have taken obstacles, taken challenges, and turned those into situations where they've been successful. Examples like that.
00:07:11
Speaker
So it pumps you up. And if you leave reading that book and you think, wow, I want to kind of take a different perspective. I want to not get so down when bad things happen. I want to turn myself, I feel now motivated in turning myself into the kind of person that can turn obstacles into opportunities. Then I think the book really succeeds in doing that. And I think that would be a total success.
00:07:35
Speaker
So that's the first thing that I really, really like about it. And I think part of probably the reason why Ryan writes using so many anecdotes rather than getting into the nitty gritty of ideas is that unless you're pretty far along your stoic journey, the nitty gritty of ideas.
00:07:51
Speaker
It's not that motivating. It's not the kick in the butt that you need to get going, but reading some inspiring examples of whether those are ancient generals or Benjamin Franklin or modern athletes, reading these stories of these people who have achieved great things, that is just motivational by proxy, and it's something that the book does really, really well.
00:08:15
Speaker
I agree with that. That's one of the items that I have on my list for good aspects of the book. There are a panoply of concrete stories of people weathering hardship. And it's always useful to have specific people you can emulate. So he tells a story about Edison's factory.
00:08:40
Speaker
our set of his factories. Catching a flame and Edison's response is, you know, forget all the kids out. This is the largest fire they'll probably ever see in their life. Or retell the story of Marcus Aurelius managing
Core Stoic Concepts: Opportunities in Obstacles
00:08:55
Speaker
the coup of Avidius Cassius with grace, with forgiveness, but strength as well.
00:09:05
Speaker
And having those stories as specific examples of people who weathered hardships is a useful existence proof, especially if you're just experienced an obstacle or if you want to improve your craft profession and are currently facing obstacles. Yeah. And so to build on that.
00:09:33
Speaker
Like, so the entire book is about, the entire book, I would say is kind of centered around this core stoic idea that there exists opportunities for improvement in things that seem difficult. Whether that improvement is, you know, like a business opportunity or whether that improvement is learning something about yourself, about your ability to withstand hardship, whether that opportunity is just observing a silver lining that we would otherwise forget.
00:10:02
Speaker
So it's a collection of probably at least 50 different stories of historical figures that have done that. And as you said, that's a useful kind of repository or repertoire to have in your back pocket to pull upon or to think about. And so going back to my three-part division between olynchic, protreptic, and didactic, and forgive these
00:10:22
Speaker
these obscure words, but basically, you know, educational kind of art, debating argumentative and then like inspirational. These stories are both educational and inspirational. So they're not, they're not educational and like, let me sit down and list out the arguments piece by piece, but it's educational in that, well, if this person did it, then I can do it. Or I get to observe a master or an expert kind of navigate that, that difficult situation well. And that that's educational in a way.
00:10:49
Speaker
So I guess I would say it's not just, I argued before that it was inspirational. It's not just inspirational, it's educational. And that's great. And one thing we talked a lot about on this channel, on this show is the contemplation of the sage exercise, which is a practice that the Stoics recommended, which is in a difficult situation or really in any situation where you want to know what to do, you consider what a great person would do in that situation. Somebody either you know, or somebody that you've heard about. And.
00:11:16
Speaker
In order to contemplate the sage, you need a lot of different sages and you need a lot of different situations that sages have been in. And just as a collection of those kinds of stories, maybe these people aren't sages, but they're, for the most part, great, excellent people to navigate extra, extraordinary situations really well. And I think that's a, that's a huge plus to have. That's, that's nothing but positive to have. Right.
Critiques on Stoic Depth and Moral Stance
00:11:41
Speaker
Right. Yep. Absolutely. Cool. What else do you have on the good side?
00:11:44
Speaker
I mean, the other thing I guess would be to respond to criticism. Sometimes people criticize Ryan Holiday.
00:11:50
Speaker
And I'm going to criticize Ryan Holland a couple of minutes from now about getting things wrong, about not understanding stoicism, about simplifying stoicism. And I think he does that. I do think he doesn't understand some things, at least, you know, this is 2014. If you, if you look at the things that I wrote in 2014, I didn't understand a lot of things that I know a lot better now, at least back then he didn't, you know, there was there, he was certainly at the beginning of his, of his learning journey or maybe at the middle of that journey.
00:12:19
Speaker
Not at the end of it, certainly. And then there's other people that I think kind of turn up their nose, which I would say is actually just this kind of elitism of like, oh, unless it is the most hard, difficult, obscure form of engaging with this topic, there's no point in engaging with it. You know, there's no value to something that's well written, easily written, enjoyable.
00:12:40
Speaker
And I think the other thing I'm pushing back against is that's wrong. We need in any hobby, in any interest, in any passion, you need popularizers. You need people who are able to take difficult topics and turn them into writing that is compelling and interesting to people.
00:12:58
Speaker
And I think Ryan Holiday is a really good popularizer. I think this book is good popularization. And that has a consequentialist benefit of getting more people into stoicism, more people interested in then going down that, that journey to learn more about it. But even if people don't learn more about it, I guess I just want to clarify that, you know, not everybody's going to be a 10 out of 10 super interested in something. If, if somebody.
00:13:24
Speaker
hasn't read a philosophy book in years and picks up this book, I think this book is going to net positive for them. I think they're going to learn a couple interesting tidbits of stories and gain a couple perspectives that they're going to want to apply
00:13:37
Speaker
Um, about these basic stoic arguments about, you know, I, it's better for me if I, if I manage my emotions well, I should consider what's up to me in these kinds of situations. I should understand that there's always something, some way for me to turn the situation to my benefit. I should be able to.
00:13:57
Speaker
follow a process I've set out for myself and not be discouraged if things don't go my way. I should not attach myself to certain outcomes and then be too disappointed if those outcomes don't come about. That might, it might teeter on the edge between a kind of
00:14:13
Speaker
general self-help versus stoicism, but general self-help is still helpful. These are still good, helpful points. And I think for the most part, if it gets people into stoicism, which it obviously has, then I'm super, super happy about it. I think that's a major net positive. Any book that's able to do that?
00:14:35
Speaker
Yeah, in my view, it's written for progressors who are interested in stoicism as a tool or at the level of an operating system. So in our discussion on the Silicon Valley stoicism, we distinguish between three different levels of using the philosophy. One, you have the tool belt.
Stoicism as a Life Philosophy
00:15:00
Speaker
life hack approach which just takes specific tactics, precepts, whatever from the philosophy and applies that to... You can just grab those off the shelf, apply them to your life, move on to the next thing. Maybe you do this to hundreds of other philosophies.
00:15:22
Speaker
The other approach is a step above from that where you take this philosophy on as a proper operating system in a way you think. I'm a stoic and it's given me the tools to navigate handling hardship, to manage my negative emotions.
00:15:44
Speaker
And you've ingrained the worldview more deeply than you would have if it was just a set of life hacks. And then the next level up is now you've taken it on as a life philosophy. Not only does stoicism have all these practical aspects to it, but it provides a direction to your life and an account of what it is to live the good life.
00:16:07
Speaker
And for the most part, I would say this book is hovering around the first and second levels. So it's not.
00:16:17
Speaker
merely a book of life hacks, though it does have that, but it's principally, I think, an extended example of people who take on a stoic attitude in a limited way for handling obstacles. So you have these three sections that you mentioned.
00:16:38
Speaker
Earlier in the book, there are these three sections that you mentioned earlier, the perception, action, will, and the themes of this operating system are on the perception side when obstacles arise. Either they aren't truly obstacles at all, you can see them as they are, or you can summon the ability to see what's good in it. You can alter your perspective.
00:17:03
Speaker
On the action side, there's always a play. You have chapter titles like follow the process, do your job, do it right. And then last on the will side, you have the power.
00:17:18
Speaker
within yourself to overcome obstacles is one reading of what he's saying in the side of the will. You have the power to persevere. And all these three approaches to obstacles come together in a view, a style of approaching hardship, of approaching adversity.
00:17:41
Speaker
One thing you can expect from this book, I think is a better sense of what a practicing Stoics operating system is for many kinds of hardship. But, and I think as we'll talk about a little bit later, there's a question of, is it, does it give you enough to come with the life philosophy? Yeah, totally. So just add to that, to frame those three sections differently.
00:18:12
Speaker
You know, I like the way you frame that he's basically saying, you know, when an obstacle, when you encounter an obstacle, when you encounter something that's kind of stressful, difficult, hard for whatever reason, you can think about it differently. That's perception. You can do something differently. That's action. Or you can want something different that will. And so there's this kind of, this kind of three step process that I is very, I wouldn't, I'm about to argue for this in a bit, but I wouldn't say it's.
00:18:43
Speaker
It is what a stoic would do, but a stoic might do it for different reasons than I don't think Ryan gets into it. Well, he doesn't get into in this book, which I think is the difference between that, that maybe first or second or third level, as you talked about.
Action and Motivation Over Theory
00:18:56
Speaker
Anything else you wanted to say about the parts you really liked about the book?
00:19:00
Speaker
Yeah, the last aspect is it's always focused on action over trivial debates. That's one can go too far in that direction, but there is something to that approach. And there's a, I think a reason why so many people in a different fields, whether it's athletics, art, or business have found this an inspiring and motivational work. And it's because of that focus.
00:19:30
Speaker
on action, that real practical aspect to the work that comes out I think is a kind of energy that one gets to sense that.
00:19:42
Speaker
Ryan Holiday takes his craft really seriously. He works exceptionally hard and that comes out, I think, in the book. He works hard, he works fast, and cares about being a good writer along multiple dimensions. So there's focus on action, focus on craft, comes out of the work.
00:20:03
Speaker
Yeah, it's like Nike, just, just do it. You know, it's the, that, that focus, that focus absolutely. And I think you hit on something nice there too, about how there in, in the act of, in the act of, I always think about this with, with authors is they, they often write these books about self-transformation or self-discovery or self, but there's this sense that the self-transformation discovery or challenge they're encountering is writing that book.
00:20:32
Speaker
You know, so you have this person, right? Holiday engaged in this difficult process of writing books, becoming, you know, holding this craft. And then in that process, he's, he's writing about that craft, right? The same way the next book ego is the enemy.
00:20:46
Speaker
is about his ego as we're like that kind of second album, you know, where the band writes in response to success. The band's second album is about achieving success in the first album. The second book is about, well, now I have a popular book and now I have to work on my ego. It becomes the new part of the process. There is something autobiographical in that that I think is interesting and inspiring too. Yeah. With Holidays Korea in particular, you have this
00:21:13
Speaker
focus on doing really I think he I don't exactly remember when he wrote this he's probably around 25 or so so he's not that old he's he's working long hours moving quickly hasn't really hit his break yet
00:21:31
Speaker
And then later on, as you say, you go as the enemy after more success. Stillness is key. I haven't read either of those books, but you know, maybe he's too busy. And now his most recent series is of course on the virtues. So he's bringing, bringing back a sense of direction after the early man's game of facing obstacles and pulling all nighters and so on. Yeah, cool. All right. That's the good. What do we have on the bad?
00:22:01
Speaker
Yeah, so I'll start it off, jump into this, get all pumped up. I think you already hit on it though. So my first criticism of this book as somebody who is quite far along in their stoic journey, I'm not a stoic beginner coming from my perspective, which is a unique perspective. It's not the same thing as if someone in my family or friend of mine was reading it who hasn't read anything about stoicism.
00:22:21
Speaker
I think Ryan here is at his most shallow. I think he's much more shallow in his discussion of stoicism than he is in his blog, which I've, I've read a bit of and the daily stoic and.
00:22:33
Speaker
In that work, I think he gets into the nitty gritty of some of it. In this, it's at a very, very high level. The litmus test I use, you know, something like, could this advice apply to a serial killer or a bank robber? And if it could, then you're at that level of being a toolkit, right? You know, you.
00:22:52
Speaker
I could use a hammer to build my house and a serial killer could use a hammer to kill somebody. That's a tool, right? It has no innate morality to it. The hammer is just a tool. And so I look at these, I listed some chapter titles, right? And the lessons there are not any different than the chapter titles. Trust the process, persist, take action, look for opportunity and defeat. Know that you can always try, accept obstacles.
00:23:19
Speaker
Really motivating stuff, but all of this could apply to a bank robber who's getting discouraged before the big heist, right? And it's just, it is this, these are preptic motivational pieces of advice for somebody who's getting discouraged by difficult things. It doesn't connect to any of, I would say the core moral values of stoicism.
00:23:42
Speaker
For me, the core moral value of stoicism is that virtue is the only good. And I would even consider somebody a stoic if they were to say virtue is the greatest good and significantly more important than other things, but yeah, I still like having, you know.
00:23:58
Speaker
I still like having some other things and they're kind of good too but there there's no discussion in this book of character being the only thing that matters like look it doesn't matter if this happens to you it doesn't matter if your house burns down because you still have your character it doesn't matter if somebody makes fun of you because you still have your character it doesn't matter if you lose a bunch of money as long as you navigate that situation with good character with courage honesty kindness there's no discussion of things like that instead the chapters are
00:24:27
Speaker
You know, examples of, well, this person, you know, lost, lost their money and then ended up getting more money later or something like this. And that's an inspirational story to not be, to not make. And I think the stoic would agree that when you encounter a difficult situation, you don't want to add false judgments. You don't want to think, well, my life is over.
00:24:48
Speaker
things are ruined, there's nothing I can do now.
Stoicism vs. Common Sense Morality
00:24:51
Speaker
And so a stoic would agree with that half of it, but there's none of this connection to that core moral teaching about the importance of character above externals, as the stoics would call it. And so for me, it just keeps that thing, for me that puts it at the toolkit level.
00:25:05
Speaker
And in that sense, I can't call it a stoic book. I think this is a stoicism inspired book. I think this is a book that was inspired by stoicism and teaches people about some of the good things stoicism has to offer, but I don't think it really teaches people about stoicism proper.
00:25:22
Speaker
And, you know, I'd be interested if anybody's listening to this has gone through that journey of starting with holiday and moved on. If you then find stoicism to be this big shift, because it's, it's, it's arguing these different things or maybe it looks like different than you might have thought it was coming out of this book. And so that's my biggest objection to it. And I think that's most, more, mostly an objection within the context of who Ryan holiday is now, who's someone who's established himself as kind of the, the leading authority, at least in the public sphere on stoicism.
00:25:53
Speaker
And so if you know that about Ryan and you go and you read this book and you might think, well, okay, God, I've just read this book about stoicism. And I don't, I don't think you actually have is what, is what I would argue. I think you've read a book about turning obstacles into advantages of which of course the stoics have some good things to say about it. That's, that's number one. What do you think about that? Yeah. Yeah. So there's the arguments.
00:26:16
Speaker
There's sort of two levels of argument. There's one, can this advice apply to a serial killer or bank robber? Is it morally neutral? But there's also the point that supposing it's not morally neutral, is it, does it have a moral stance that's properly stoic? And so, and I think your case is that
00:26:41
Speaker
Well, since being a serial killer or a bank robber is not morally stoic, it's neither of those. But I would suggest that it's the, the second argument's probably better than the first. No, not only does he cite different lines from Marcus Aurelius, of course you have the three lines
00:27:04
Speaker
which is a definition of stoicism in some sense, right objective judgment at this very moment, unselfish action at this very moment, willing acceptance of all external events. That's all you need at that line.
00:27:19
Speaker
as well as praise for a number of virtues, whether it's being unselfish or forgiving, courageous throughout the book. So I would say that there's no sense in which this book would support being a serial killer. If anything, its morality is somewhat conventional.
00:27:41
Speaker
One could argue that the book would defend, say, a kind of morality that's at the edge of conventional morality, say being a business magnet, being exceptionally ruthless in your business dealings, breaking rules in order to accomplish whatever entrepreneurial goals you might have.
00:28:09
Speaker
And if someone who had those dispositions came to this book, they would probably leave with those dispositions intact, which is certainly not the stoic view and not the stoic result, if you will. So in that sense, I think the argument that I find more plausible is that Ryan just doesn't
00:28:33
Speaker
explicitly state the aesthetic view about the importance of virtue. You have all these heuristics for managing obstacles and hardship, but he's too liberal and he's too open as to why someone would want to
00:28:55
Speaker
do that at all, or what really grounds the ability to manage hardship in a way he stays at a conventional, almost common sense level in explaining these things. Does that make sense? Yeah. That's a really clear way of putting it. I mean, I wasn't certainly not trying to imply that right nowadays that the obstacle is the way is like endorsing serial murder or anything like that. But I think you pointed out that.
00:29:25
Speaker
It probably could, if not endorse, you know, somebody who's kind of a ruthless business person could leave and be like, yeah, that's a great book that kind of pumped me up to go do some more ruthless business in a way that like involves lying and cheating to kind of build my business. And we don't want that. Or I think the stoics wouldn't want that. Well, it depends on the rules, but yeah. Yeah, depends on which ones. And I think, I think, I think you said it best though, in terms of there's a kind of common sense morality here, but stoicism is very not common sense morality.
00:29:56
Speaker
And in that sense, if you're leaving a book feeling like this is very common sense instead of, wow, most people when they read an actual stoic say, wow, I've always felt this way. And I've always felt weird for feeling this way, or I've always felt like nobody's really put this into words until now. And this is amazing. Or someone says, that's really stupid. Stoics are terrible people who don't care about others. And you know, maybe that's uncharitable, whatever, but it evokes a strong reaction.
00:30:23
Speaker
because stoicism is paradoxical, it's counterintuitive, it's not common sense. It wasn't common sense in ancient Greece, and it's not common sense today. And so if you leave this book feeling unchallenged ethically, then you're probably not reading about stoicism. I think it's kind of is my thought. Yeah, I would say I'd say that's a
00:30:44
Speaker
I'm sympathetic to that. I could say this book gives you the ingredients to think about stoicism and whether or not you take them is going to depend on the reader to a large degree. In part, just because it doesn't take that strong stand on what's the telos of human life. What is the purpose to live it all, let alone to endure hardships?
00:31:15
Speaker
Totally. Yep. Yeah. I think that's, that's related to my complaint. Well, I don't know if this is my key criticism, but it doesn't have a systematic
00:31:33
Speaker
philosophy and in some ways I think it's organization mirrors that fact. It reads at times like a series of blog posts. That's good because you can jump in and out of these chapters and it does have a coherent style or message but not a clear logical progression
00:31:57
Speaker
or a deeper theoretical basis. And although it's true that Stoic philosophy is largely practice, it is theory as well. And you need that theory to justify practice or guide practice at times. So that's one complaint I have about this book. Yeah, I agree. I totally agree. And I don't think that's intentional. I think the underlying structure just isn't there.
00:32:25
Speaker
I don't think this is somebody who understands the underlying structure of stoicism, at least not 2014 Ryan Holiday, which is not the person he is today. It doesn't strike me as someone who understands the underlying structure of stoicism and then is choosing to simplify. It strikes me as somebody who is misunderstanding the theoretical background or doesn't understand the theoretical background. And so there isn't a system in place because he doesn't have a system.
00:32:52
Speaker
The system that's provided is, is the three, the three part division between perception and action and will, but that's not a system so much as it is kind of a coloring of the conversation about, I guess the different ways that you could approach it, an obstacle through how you think about it, what you do and how you feel about it.
Meditation and Emotional Insights
00:33:11
Speaker
practice stoicism with stoa stoa combines the ancient philosophy of stoicism with meditation in a practical meditation app it includes hundreds of hours of exercises lessons and conversations to help you live a happier life find it available for a free download in the play store and app store do you want to jump into that some more
00:33:32
Speaker
Yeah, so this comes up to my theoretical, and I don't want to sit here and nitpick a book written 10 years ago, but at the same time, it's interesting for people that maybe have read this book to get a different perspective on it. I think Ride Holiday makes some theoretical mistakes that are important because of practice.
00:33:50
Speaker
It's not like, oh, you made a mistake and I caught you. But if you don't understand this, it impacts the way that you think about your practice. It impacts the way that you think about being a Stoic. And there's two ones that I think it makes. The first is this discussion of will.
00:34:06
Speaker
So the third section of the obstacles the way is about the will, but there's no notion of will in stoicism at all that doesn't exist in stoicism. So here's a quote here from Ryan Holiday and he says, what is will? Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do and we have some agency over our situation, the will is what we depend on when agency is all but disappeared.
00:34:34
Speaker
And I'm not sure what he's talking about here. I just don't know what he means by the will. Another quote he has is, if perception and action were the disciplines of the mind and the body, then will is the discipline of the heart and the soul. The will is the one thing we control completely always.
00:34:55
Speaker
And I get very confused when I hear that kind of language about what he means by the heart and the soul. Those are not metaphors that the Stoics would have used. Again, when you talked about earlier common sense morality, it almost seems like common sense folk psychology, like the will is where your heart is. And that, I don't, again, it just, it doesn't, it comes off as nonsensical to me. So he seems to be talking about the power of reason,
00:35:23
Speaker
So the will in stoicism would correspond to, in that three-part division, to Epictetus's idea of desire, which is to say what we want or don't want. And if someone has control over us, they shut us in a cage, we can navigate that situation successfully by not desiring our freedom, or our physical freedom, I should say. And Epictetus has all these wonderful lines where they'll say,
00:35:51
Speaker
I'm going to throw you in a cage. You have to throw my body in a cage, but you won't do anything to my mind. And that's an example of Epictetus, only desiring to be an excellent person, not desiring to, or teaching his students the only desire that, not to desire these kind of external physical things.
00:36:10
Speaker
Right Holiday seems here to get Will confused with the idea of reason and assent because it says it's the only thing we control completely always. And the Stoics talk about reasoning being up to us, but it's getting kind of confused and muddled. And I think it's confused and muddled because I think it is confused and muddled. I don't think he's thought very deeply about what he means by the Will at all.
00:36:33
Speaker
And so I just find that kind of thing, the kind of thing that might be inspiring on a first reading, but it's actually really unhelpful when you try to practice deeper. So I mentioned before that I think popularization is good. The caveat to that is that popularization is not good if you set people up not to be successful when they go deeper. And one of the ways you set people up not to not be successful
00:36:55
Speaker
is you inculcate or you teach ideas that are different from stoicism, such that there becomes this kind of clash or people end up into things with misconceptions. And I think that's one of those things that's going on here with the discussion of the will. But any thoughts that you have on on holiday's talk of will?
00:37:16
Speaker
The way will is defined is confusing. I think it's somewhat mysterious, ultimately. It's related to this conventional sense in which someone might talk about a soul, who you ultimately are. Perhaps you can even use the word spirit, and in the sense,
00:37:33
Speaker
Ryan's not exactly stoic. You know, there's the line that people often attribute to Victor Frankel, which is between stimulus and response, there is a space. And in that space lies our freedom.
00:37:53
Speaker
And I think what Holiday is saying is the will is what occupies that space. And it's always there, you know, it's there even when agency has almost disappeared is one of his lines. And I don't think he's exactly going to fill out what that is. Maybe you have some sense that there is something there and there is a reference to that term or not.
00:38:23
Speaker
all holiday I think is once his reader to agree with is that there is something there, whatever it is, whether it's a unified being, whether it has parts, those are more theoretical issues, trivial issues that he's not going to deal with. Yeah, I'm getting stressed, Caleb, just you talking about it, stressing me out. Because the thing in between impression and
00:38:49
Speaker
ascent or the thing in between situation and action, that is our perception. That is our faculty to reflect on things and our ability like the stoic who call a sense or reasoning and what he has put here as perception and he's just muddling those concepts. He's muddling those concepts because he's coming into the book with a common sense understanding of soul, a common sense understanding of free will and
00:39:14
Speaker
or essential cell that the stomachs just don't have. And it just, yeah, he's just confused. He's just confused. And I would have been confused if I was writing in 2014, but I think it's just frustrating because it will probably confuse other people, even if it seems intuitive.
00:39:34
Speaker
Yeah, I think this is probably his, the weakest part of the book philosophically. The chapter headings are on building your own inner citadel, the art of acquiescence, perseverance, mortality, and they're less connected, less conceptually connected than the organization of the previous two sections. And I think that is just because this notion of the will is
00:40:04
Speaker
vague. And you could mount a defense of it being vague, perhaps. But, you know, I'm not going to do that here. You could, but I will not. No, fair enough. And I guess what's frustrating me about the vagueness is it's not like it's vague, like nobody's ever solved this. It's vague. And the stones have something to say about it. Like, and there's an ant like they've said things about they say many things about this.
00:40:33
Speaker
They're very clear about, if you read Epictetus once, he's very clear about this, about what the self is, what our essential self is. So that's the kind of thing that's frustrating to me, is not that it's like, I understand why some, why, you know, if you haven't studied stoicism yet, if you haven't studied philosophy yet, yeah, you know, you're in a first year stoicism or first year philosophy class, or you're getting into reading philosophy on your own for the first time, and you have this question of like, what is the will? That's a really interesting question. That's a great question to ask. I'm not saying it's off the table.
00:41:01
Speaker
I just still haven't answered that question. And I agree with it or disagree with it, they haven't answered that question. And the fact that Ryan's not bringing that up at all, it's frustrating to me because as you said, the other two sections I think are stronger and I think it's actively harmful in terms of perhaps confusing people. But I'm happy to jump on my next one. I'm not sure if you have one you want to go into.
00:41:26
Speaker
No, I, that was in fact, one of my bullets was just that the use of will obscures more than it illuminates. So yeah, let's see one more each you can take to your, to your next one. Cool. Yours was better. Yours was better written than mine. That was, I think well, well framed obscures more than it illuminates.
00:41:44
Speaker
So my other one is that Ryan Holiday, so people get into stoicism often because they care about their emotions, right? They want to feel a certain way or they want to help control in their emotions or they aspire to be stoic when they take themselves to be quite not stoic in an emotional sense.
00:42:00
Speaker
When you read this book, Holiday either doesn't understand or believe the cognitive theory of emotions. So the cognitive theory of emotions is one of the main stoic points. I would say if the Stoics had a key psychological or descriptive insight, their key descriptive insight is that our emotions are the results of our judgments, our value judgments in particular. And their key moral insight, I would say, is that virtue is the only good.
00:42:26
Speaker
Or at least they would say the only good. And there's no discussion of emotions being the results of our judgments, essentially. There's this idea that we can perhaps control our emotions. There's this idea that we can control our perceptions. But I don't see this idea in this book, which is the key insight that the Stoics have, that our emotions are the results of our judgments only.
00:42:55
Speaker
I have a quote here says, it's much easier to control our perceptions and emotions that it is give up our desire to control other people and events. It's easier, easier to think and act than it is to practice wisdom. And again, it's like, I feel like all the stoic ideas have been thrown in a blender.
00:43:13
Speaker
and smushed around a bit. What do you mean it's easier to control our emotions than it is to give up our desire to control other people and events? Our emotions come from our desires, which come from our judgments. We, we feel frustrated because the thing we, we can't get the thing we want. We feel sad because we've been the thing we didn't want to happen happens. So.
00:43:37
Speaker
Again, when you said common sensuality, something clicked in for me. It is common sense talking of emotions going on here. But again, when you do that, not only do I think you confuse or obscure some of the important parts about stoicism, but you miss some of the important parts about stoicism. And I think that's a shame because I think that idea of emotions is totally on brand for a book about navigating obstacles.
00:44:01
Speaker
Yeah, well, I think he's probably just not entirely clear about this. I think someone can certainly come away with the main kernel of the cognitive theory of emotions, which is that our judgments shape our experience of the world, how it feels to exist, what we want, and at times he will
00:44:25
Speaker
give stories that show this or we'll mention, give a quote, say that from Viktor Frankl or something of this sort that suggests we are radically free and we're radically free in virtue of our ability to decide what happens and we're not limited by externals or even by parts of the internal world.
00:44:55
Speaker
And the language, it's not going to be entirely precise. It's not going to be a cognitive model of emotions in the way that Epictetus may have portrayed it or in the way that contemporary philosophers would put it. And it's going to result in people perhaps.
00:45:16
Speaker
losing track of what they do or do not have control over perhaps muddling through ideas of emotions desires and so on but there's a you know he could have done this better but i would be too too hard on him on this on this point that's certainly not as bad as the discussion on the will he has a very charitable that's fair i mean speaking of the the previous point i think we're on the same page here about
00:45:42
Speaker
I don't think he goes against it. I guess just to clarify, I don't think he goes against it. I don't think he argues the opposite. And unlike the will, I don't think he introduces a concept that doesn't need to be there. That just makes things more confusing than it should be if it wasn't there.
Practical Examples vs. Theoretical Exposition
00:45:55
Speaker
But he's missing a really good shot. I guess this is like a missed opportunity more than something that is being introduced. That's actively confusing like the will. Maybe I'll back down to that.
00:46:09
Speaker
God, I got it. Yeah, I see that. I'm not sure if I push back on that so much, but his whole approach is just more in terms of, there's this term, ostension, just showing particular examples rather than so much giving the theory for why so and so is the case. I said he'll give a story, provide some motivational
00:46:39
Speaker
quotes, lines, and he might argue that's more useful than giving someone a workable theory of emotion. Maybe that's not what people need to verbalize. That might be a different way of framing what he's up to that provides some amount of defense.
00:47:03
Speaker
Anyway, we're actually, yeah, we're starting to run a little bit low on time. So, I'll note one other criticism, a quick criticism. There's very little religious or spiritual sense to the project.
00:47:17
Speaker
He has a line that denigrates religion, which I have to read out, which is a few years ago in the middle of the financial crisis, the artist and musician Henry Rollins managed to express this deeply human obligation better than millennia of religious doctrine ever have.
00:47:36
Speaker
where the deeply human obligation refers to a sense of altruism, and then it finishes to give a rather pedestrian statement from Henry Rollins, which is crazy. It's the same thing to say.
00:47:54
Speaker
He does gesture at ideas of fate, but I think at least one should as part of expressing what the Stoics are up to. Since it's obviously present, especially in Marcus Aurelius, there's these ideas about nature, ideas about deeper purpose that at least deserve gesturing at. Which to my extent may continue to be a blind spot in the way he is portraying Stoicism.
00:48:25
Speaker
But I haven't read stillness's key. Perhaps he gets into these kinds of ideas more in that book. Cool. Want to shout out anything that is interesting and then call it? Yeah. Sorry, my page with my notes has frozen now. So I'm trying to, I'm unable to access my notes.
Order of Stoic Disciplines and Teaching Challenges
00:48:43
Speaker
Well, you have the three stoic disciplines are that's one header, the obstacles, the way strikes needs ultimate toolkit book.
00:48:51
Speaker
Okay, here we go. Back in, back in. They're mostly just more criticisms. They're mostly, they're mostly just more criticisms. Yes. So. I mean, so, so, so the, I mean, this wasn't this one, this is something that I thought was interesting because.
00:49:06
Speaker
You know, you can't, so Ryan Holliday has become probably the most successful contemporary teacher of stoicism, at least in terms of number of people. And you can, you know, I think he generally does a pretty good job here, as you said, of representing well, kind of a level one or a level two, either toolkit or an operating system level of stoicism kind of fluctuating between those two. But one thing that he's really good at, he's really good at getting people engaged in these ideas, finding these interesting
00:49:36
Speaker
And one thing I think is interesting is that the Stoics talk about the three disciplines as being desire, action, and ascent. And Epictetus is really explicit that those need to be practiced in that order. So first you need to work on what you desire.
00:49:54
Speaker
making sure you only desire what is good. Then you need to act correctly about navigating externals and indifference. And then you need to get your ascent right. And if you start with ascent, you get all mixed up. If you start with action, you get all mixed up. You got to follow this order and you got to master one before you can master the other. You can do all three, but you have to master one before you master the other.
00:50:16
Speaker
It's interesting for me that Ryan Holiday actually flips these three. So his book starts with perception. His book starts with this discussion of ascent, how you view things, how you look at situations. Then action is in the middle. And then will, what you desire, what you aim towards is the last thing. So he switches the order. And I think stoicism is stoicism, but I don't think the ancient stoics necessarily need to be right about the best way to teach stoicism.
00:50:46
Speaker
The non-critical way to look at that would be, well, why has that been switched? Is there something to learn there? Is there something interesting about focusing on perception first?
00:50:59
Speaker
And I think maybe one of them, it happened for you to jump in on this Caleb. Maybe one of the reasons you start with perception is that's the easiest way to get people in. Desire in a way is the hardest thing to change. What people want, what they think is good is the hardest thing to change. But perception, pointing out to people, look,
00:51:17
Speaker
you know, if you viewed the situation differently, you're going to feel different. That is maybe the easiest introduction. I guess I'm interested in his playing around with the order of these disciplines, which are ones that, you know, we take seriously here, use in the STOA app to help teach people as well. Right, right. So Pierre Hadeau, the French philosopher, who was one of the key figures of reviving stoicism as a philosophy of life,
00:51:43
Speaker
He orders the discipline by assent desire and action in his book on Marcus Aurelius.
00:51:59
Speaker
There's a whole, there's a whole other can of worms, I suppose, here about how you, how you organize that. But I followed in the past in several of our courses, Hadoas, ordering, because there's that initial focus on apprehending reality accurately, pursuing knowledge.
00:52:24
Speaker
And then moving to will, desire, aligning your desires with nature. And then finally there's action, acting in the world, managing indifference. So I think that's it. That's how I thought about it before being less sort of influenced by hepatitis's original formulation.
00:52:52
Speaker
Yeah, that's an interesting way of putting it. I mean, I think Epictetus's concern is that if you start with perception, it's this kind of a level one, level two concern is that if you start with perception,
00:53:02
Speaker
tricks about changing our perception that dichotomy of control you can almost frame as a perception tool the view from above the contemplation of the sage a lot of these things you can do is well just kind of look at things obstacles the way kind of look at things differently that can be co-opted to many to common sense morality it can also be co-opted by
00:53:23
Speaker
you know, anti-ethical systems. So I think that's kind of, that's Epictetus's concern, but I'm not, I'm not necessarily, I think that's what Epictetus thought, but I don't necessarily think it's the right way to do it. And I think the fact that Hadeau portrays it differently than Holiday, it's kind of funny. He's got many, many different ways to attack it.
Conclusion and Final Thoughts
00:53:43
Speaker
Yeah, yeah, that's right. The one aspect that I thought was interesting is that the title of the book, one of Marcus Aurelius' lines, of course, from Meditations. And I think we can end just by me reading that line out at Meditations 5.20 because there is a whole section there and I think
00:54:12
Speaker
It's provocative and totally underrated what Marcus, the context in which Marcus Aurelius is saying this.
00:54:21
Speaker
He says, in a sense, people are our proper occupation. Our job is to do them good and put up with them. But when they obstruct our proper tasks, they become irrelevant to us, like sun, wind, animals. Our actions may be impeded by them, but there can be no impending our intentions or our dispositions. Because we can accommodate and adapt, the mind adapts and converts to its own purposes the obstacle to our acting.
00:54:50
Speaker
The impediment to action advances action what stands in the way becomes the way And perhaps we'll just leave you with that so it's another good conversation Thanks for chatting Michael. Thanks everyone. Thanks kelp
00:55:08
Speaker
Thanks for listening to Start Conversations. If you found this conversation useful, please give us a rating on Apple, Spotify, or whatever podcast platform you use, and share it with a friend. We are just starting this podcast, so every bit of help goes a long way.
00:55:24
Speaker
And I'd like to thank Michael Levy for graciously letting us use his music. Do check out his work at ancientliar.com and please get in touch with us at stoameditation.com if you ever have any feedback or questions. Until next time.