The Obstacle Is the Way

The book that started a Stoicism revivalist movement, The Obstacle Is the Way is Ryan Holiday’s way of figuring ancient philosophical ideas in the modern world.

The idea is that the reader can take away Stoic ideals without having to take a deep dive into the likes of Epictetus or Seneca. Less to do with ancient logic and metaphysics, and more the question of, “What is the good life?” Which is probably best for a book aimed at the general public. The book’s thesis is taken directly from Marcus Aurelius — what blocks your path can become your path. Holiday organises the book into three fundamental principles — perception, action, and will. Of course, how that framework lands depends entirely on the person and where they are in life.

The Obstacle Is the Way arguably seems geared towards a young person finding their feet. Probably creative and entrepreneurial types primarily, but you don’t necessarily have to be those things to enjoy it. For someone in early adulthood, there is no shortage of obstacles. Career uncertainty, financial pressure, social pressure, academic performance if you’re a student, anxiety about “falling behind,” or just generally not being where you thought you’d be. There’s a lot going on. This book — and Stoicism 2.0 in general — is great for reframing your mindset and picking yourself up off the ground when you’re down.

There is a tendency for younger people to frame obstacles as personal, and a text like The Obstacle Is the Way can help one see that they are more situational than anything. And if that’s what you’re into, then I suggest following Obstacle with Ego Is the Enemy, and Stillness Is the Key. All three texts are part of Holiday’s trilogy on Stoicism for modern times. I have the box set, and it’s always good to have on the shelf.

You can say that it’s better to learn from experience. I tend to agree, but sometimes it’s hard to know where to start. I know how that feels, and it sucks. A book might not have (m)any concrete answers, but it can give you that little nudge out of the door. That’s where the value lies.

For myself and probably many others, The Obstacle Is the Way is more of a handy reference than a how-to guide. I read it when I was finishing my undergraduate degree, and I already knew teaching was what I wanted to do. I was already familiar with Stoicism. Meditations by Marcus Aurelius, Letters from a Stoic by Seneca, The Discourses by Epictetus, Man’s Search for Meaning by Viktor Frankl, and The Inner Citadel by Pierre Hadot had been staples in my library for some time. I’d recommend those texts to just about anyone; they’re fairly easy to get into and nowhere near as tough as Hegel or some analytic philosophy.

Now, I’m on the downhill of my thirties. I’ve been teaching for a decade. I’m on the career path I’ve chosen, and I like to think my values are more or less settled. I know what I like, what I believe, what is bullshit, what resonates, who says it, how I want to live my life. I don’t have it all figured out, but I like to think I have a good sense of who I am and where I’m going. I am a humble classroom teacher, something I am perfectly content with. I’m not out there hustling my grind, thinking about my Lambo.

That, and I originally bought it because I liked Ryan Holiday. Trust Me, I’m Lying was already one of my favourite books, and I’d enjoyed his blog since the Rudius Media days. He used to post on the forum under the username iron_maiden, and his frequent quoting of Marcus Aurelius endeared him to the site’s owner and his inner circle. I took a lot of his reading recommendations at the time, and still do.

So with that said, The Obstacle Is the Way is a very accessible, concise introduction to Stoic philosophy (or aspects of it). Holiday’s blend of storytelling and historical example — John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, among many others — is style and substance all in one, and I think that really helps bring the reader in. And then, perhaps one can go deeper, exploring some of the Stoic authors mentioned throughout the text. That’s a rule I follow — if I like a book, then I have to check out at least one text in the bibliography. Takes me places, it does.

Some might argue that Holiday is cherrypicking Stoicism to reinforce productivity hacks, rather than exploring the full range of Stoic ethics and metaphysics. You would certainly be correct in making such criticism, but that’s also kind of the point. Holiday has never claimed to be a philosopher. In fact, I remember watching one interview where the host called him one, and he started to look really uncomfortable, cutting the interview short.

For those looking for stable ground in a world that is becoming increasingly polarised and uncertain, The Obstacle Is the Way is a great primer on what it means to centre yourself. And for the collectors out there, a tenth anniversary edition was published in 2024, with a new introduction and new chapters. Also, there is a leatherbound premium edition available if you can justify spending the money. It doesn’t offer much in the way of new content, but it does feature new illustrations and a letter from Holiday. The genuine leather cover, custom box, and Munken cream paper are nice touches as well. That is if collectibles are your thing.

At the end of the day, it’s still for reading. But do what you like.

Whether it’s his books, courses, podcast, or videos, Ryan Holiday has a wealth of great content worth checking out. He’s a far more worthy influencer for young men than Andrew Tate and manosphere douchebros currently glutting the market, and it gives me hope to see more and more young people getting into his stuff. Happy reading.