The Obstacle is the Way - Final Review

We've made it through, how are we feeling?

May 09, 2025

The biggest critique I've heard about Ryan Holiday's book is that his tone can be off-putting, giving a "I know better than you" vibe.
But is the book still worth reading?

Welcome back to Book Club!

It's been a week since we finished Ryan Holiday’s The Obstacle Is the Way. How are you feeling – different, the same, or somewhere in between?

As promised, this is my final review to wrap up our weekly series!
While the other Book Club videos are exclusive for members, this review is on YouTube, so please don’t hesitate to share it with anyone who might enjoy the book or our club.

[Especially if they're stubborn! Sometimes it's easier for our friends to join in when someone else is suggesting it to them.]

Why Our Book Club?

We created this book club because self-help books need to be experienced over time. Not just read but interacted with and integrated. Because there is so much you can get from this genre of book but if you’re not going through it with the right strategies, you’re not going to get nearly as much as you could.

Our guided videos offer perspectives and exercises to help you work through the book. But in true SELF development style, there are no meetings - so you can show up when you’re able and move along on your timeline.
Need to walk away for a week? Don’t worry, the videos will always be here waiting for you.

Why This Book?

Honestly, because I (Ariel) needed it.

Before this all began, I had just started a tough class and expected it to be easy – I was wrong. The first session left me feeling defeated and unsure how I'd manage the next six weeks. I was deflated, to say the least.
Then, I found this book on my dining room table. Someone else was reading it, but I immediately felt, "I need this."

And it helped!
As we progressed over the weeks, things turned around, and the book helped me get back on track. So for me, it was a valuable read.

I'm still curious to hear your experiences (even if you didn't connect with it.)

The Book All Wrapped Up

Ryan Holiday presents a three-part formula:

Perception: How do you view the obstacle? What's your mental framework? Is your mindset helpful?
Action: This section compiles actions Holiday suggests taking. He calls it "correct" action - by golly, do I hate the word correct. How even do you define "correct"?
I would say that Ryan gives you some guidelines to work with. In a way defining “correct” as thoughtful, strategic action and not just reacting randomly. Developing a plan before moving forward..
Will: "If perception is the realm of the mind and action is the realm of the body, Will is the realm of the soul." From where I sit, Perception and Will are two sides of the same coin. Perception is your mindset going in; Will is your mindset while you're in it. And at the end of the day, your mindset controls your dedication and ultimately, your follow-through.

What Kind of Book Is It?

First of all, you need to be open to Ryan Holiday's direct, sometimes assertive or even aggressive, tone. At times, it feels like he's telling you what to do and then looking you in the eyes while saying “And I know you’re not doing it.”

If you can handle that energy and appreciate a no-nonsense approach paired with historical examples of “great men doing great things”, this book could be useful. If that's not your style, you might struggle with it.

Fortunately, it's a short and easy read. The audiobook is under five hours, and the text is clear and simple.

Honestly, I'd recommend owning this book for the action section alone.
When facing an obstacle, you can revisit those chapters for recommended actions or use his three-part system to assess your situation: Does your Perspective need to change? Or is it your Actions that need focus?

Overall, The Obstacle Is the Way provides a good basic framework for moving forward when challenges arise.

What to Read Next?

I'm definitely curious about other Ryan Holiday books, like Ego Is the Enemy, or perhaps one of the ones on Stoicism. But I'm most drawn to his first book, Trust Me, I'm Lying, because it seems so different than the others..
It has a cocky vibe. As if Holiday knows something we don't and is laughing at us the whole time. I just can't resist that implied challenge.

Next in our book club, though, is Essentialism by Greg McKeown, which explores doing less for greater impact. And like I said earlier, I can’t wait to explore it with you all.

Final Thoughts

The Obstacle Is the Way is a good resource (as long as you are chill with Ryan's tone.) And it's an easy and relatively concise read.
While the action section could be more focused, his core premise of Perception, Action, Will is clear. Once you grasp that, you grasp the book.

Please leave in the comments what you walked away from the book with!