I know I’m a little late to the game, but I recently read Ryan Holiday’s 2014 book, The Obstacle is the Way, and I felt it merited some attention. This is in part because it has to do with Stoic philosophy, and Stoicism has seen a surge of renewed interest in recent years, especially among young men. There are good reasons for this interest. Stoicism is an important school of philosophy from the ancient world that does have a degree of power to address problems that face young men today, though, in my opinion, it falls short in critical places. Perhaps I’ll write about this topic on another occasion. For today, I just wanted to give voice to some of my thoughts about Holiday’s book.
Book Overview
The Obstacle is the Way is all about learning from Stoicism how to deal with obstacles in every area of our lives in a positive and empowering way. The book launches from two unconnected quotations from Marcus Aurelius’ Meditations:
Our actions may be impeded … but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting … The impediment to action advances action. What stands in the way becomes the way.
Meditations, 5.20
Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance – now at this very moment – of all external events. That is all you need.
Meditations, 9.6
Both of these themes are repeated in various forms and contexts throughout the Meditations. The former quotation provides the title and a loose theme for Holiday’s book. The latter provides the three-part structure – in name, at least, if not in meaning (I’m not sure how much the “Action” part of the book reflects what Marcus Aurelius means by “Unselfish action”, but whatever). Overcoming obstacles, or turning obstacles into the way, Holiday tells us, is accomplished in three parts: 1) altering our perception of ourselves, the world, and our obstacle; 2) taking intentional and persistent action; 3) not letting our willpower be overcome by adversity, setbacks, or surprises (i.e., perseverance).
An Introduction to Stoicism?
The Obstacle is the Way sets itself up as a sort of introduction to Stoicism. It both is and is not. It is a basic introduction to practical modern Stoicism. It is not an academic introduction to historical Stoicism. That’s not to say that it doesn’t have its uses as an initial guide into ancient Stoicism, but you need to know what this book is at its core going into it. I did not, and it delayed my ability to appreciate it and learn from it.
It doesn’t help that I found Holiday’s manner of expression off-putting. As a theologian, a reader of ancient texts, and teacher of children in a classical school, I think big picture questions about metaphysics and epistemology are not only important but foundational – you cannot have a coherent ethical system without them. Holiday comes across as disdainful of any philosophical questions or lines of inquiry that are less concrete than ethics or praxis. He is a pragmatist. And this is probably why Stoicism appeals to him. Stoicism as a philosophy (particularly in its modern incarnation) can often be light on the metaphysics, light on the epistemology, and heavy on the ethics. “Don’t bother me with silly questions and details. Just do it!” Occasionally, when you’re dealing with someone who is just making excuses for inaction and victimization, this kind of blunt force might be in order and might (might) be effectual. But really, this is the chief weakness of Stoicism. It often amounts to little more than moralism and pull-yourself-up-by-your-bootstraps-by-the-power-of-your-will, more emphasis on the what than on the why. This makes the book feel at times shallow if well intentioned.
Now, let me quickly say that a deeper, more generous reading of the book makes it clear to me that Holiday is not actually quite as uninterested in the big picture questions as he sounds at first. Rather, he adopts a rhetorical strategy aimed at unrepentant pragmatists in order to convince them that Stoicism is, actually, a philosophy that they might be able not only to stomach but to benefit from.
It Needs a Generous Reader
And this brings up a recurring theme for me and this book: I had to read it generously intentionally. At some point I had to decide to read it in the best possible light and not objectively based on its own merits. I can thank a friend of mine for helping me to make this decision, and I also want to agree with my friend that Holiday is actually much better in video and blog format (“The Daily Stoic”). The book is plagued by inconsistency that, when read ungenerously, borders on incoherence. It isn’t necessary to read the book as incoherent, but it opens itself up to that criticism through carelessness. Some of the grammar or word usage errors (that no editor caught?) work against the book’s credibility (again, when reading it utterly without generosity). Example: the quotation of the KJV’s translation of Proverbs 24:10 that begins one chapter goes like this: “If thy faint in the day of adversity, thy strength is small.” It’s a typo, but it’s one that looks less like a typo and more like ignorance of the English language. Unfortunately, most Americans would laugh and roll their eyes were I to point out to them that it should be “If thou faint…” not “If thy faint…”, mockingly muttering “What’s the difference?” Well, only the difference between saying, “If you faint…” and “If your faint…”. The point is, we are not that far removed from the point in history when knowledge of how properly to use “thou/thee/thy” would have been common, but we are very far removed from that knowledge being common, because we live in a barbarous age whose barbarism is growing rapidly and aggressively. If you are claiming to be talking on a higher, philosophical level, your language and your attention to linguistic details need to back that up.
The book does get better in the latter two thirds, but the first half of the book had me wondering what all the fuss was about. I do actually think there is good in the first part, but I think it is concealed by carelessness in terminology that has the effect of self-contradiction on a surface reading (the chapter entitled “Practice Objectivity” is particularly affected by this). At other times, the book feels aimless, and it is not always easy to understand what the point of a given chapter is. The book isn’t that long, and it is definitely longer than it needs to be. This book really could have done with some ruthless editing. I do want to say, however, that one of the very best chapters in the book is in part one (“Is it up to you?”). I wish the whole book had been like this chapter: grounded in essential classical Stoic thought and very well applied to modern life. This is what the book promised and so often failed to deliver.
As I said before, this book is a book that needs to be read generously and always with its intended target audience in mind. This is not a book written for philosophers. It’s written for the average American who not only has never thought about philosophy, but who is probably prejudiced against philosophy as mere pointless sophistry that has no relevance to daily life. This assessment of philosophy is both wrong and right, since while at its core philosophy is precisely about dealing with real life and understanding real life as richly and accurately as possible, much of what has passed for philosophy is pretty vulnerable to the average joe’s critique. Holiday has endeavored to help the average joe take the first steps in philosophical thinking along Stoic lines. As a layman’s introduction to Stoicism, therefore, the book actually can work, even if it could have been better.
This is not a book that wins me over in spite of myself by the power and elegance of its rhetoric or the strength and originality of its ideas. This is a book with rough edges that I had to win myself over to (i.e., I intentionally had to read it generously). It really could use some ruthless editing to address the apparent incoherence of parts of it and the very unfortunate technical mistakes.
But, that being said, if it is read with generosity (as if Holiday were your friend whose good heart you trust and whose good purpose you know), the book improves dramatically and actually becomes something worth digesting and pondering by anyone, not just its intended audience.
Does Holiday Need the Label “Stoic”?
Here’s where I think I’ll write more in the future, but let me just express a few thoughts and/or questions:
- Do we need to label ourselves “Stoics” to benefit from whatever wisdom we may glean from Marcus Aurelius or Epictetus or Seneca? Quite a lot of what Holiday says in this book one can find in any number of other sources, including Eastern sources (Buddhism, for example). Quite a lot of what he says is consistent with things we find in the Bible.
- Holiday doesn’t really wrestle with the gloomy side of Stoicism. Stoicism doesn’t actually solve the problem of existential angst. It functionally tells you to ignore it. Why, Marcus Aurelius, should we trust that everything works out for the best in Nature? This is assumed, not argued.
- I would argue that, point for point, Christianity offers a better, more complete, more satisfying perspective for dealing with obstacles than Stoicism does. Whatever strengths Stoicism has, it shares with Christianity, though a Christian might not see these strengths without engaging with Stoicism.
- Stoicism is popular among young men for a good reason. Young men today are trying to recover something, anything that helps them understand what it means to be a man (what is expected of them as men) that hasn’t been thoroughly vilified by somebody. Stoicism seems to offer something like that. I think there are better options out there, but maybe we need to work our way through some ancient Stoic writings and see what the Bible has to say.
Bite-Sized Exegesis 