What The Obstacle Is The Way book taught me about hurdles.

I am not an avid reader, but I enjoy reading self-help or philosophy books to improve my life. This book is more philosophy than self-help. The author Ryan Holiday talks about stoics' writing by giving examples from wars and politics.

Why I read this book:

I read this book because I was fascinated by stoics' writing and how they lived lives free of worry and stress that we in modern days are overwhelmed by. I could have read the original texts by Marcus Aurelius, Seneca, and Epictetus, but for beginners, I recommend not jumping right to the originals at the beginning because they can be difficult to understand, especially Meditations, a book by Marcus. So, another reason I read it completely is because I wanted to handle setbacks in career and life better. This book also had excellent reviews and was a bestseller. But I am ashamed to say this book was on the shelf for 3 years after purchasing 🙃.

What it teaches:

1. The core of the book talks about turning obstacles upside down to your advantage.
   

2. The book is divided into three parts: Perception, Action, and Will. Let's dig into each:
   

3. The perception chapter talks about how we should change our perception of any difficulty we face in life. For example, when I lose a tennis match or get rejected from a job, my first reaction may be frustration. But perception gives me a choice. I can see the situation as proof that I am not sufficiently competent enough, or I can see it as useful feedback. A subpar tennis match can show me that my footwork needs work. A job rejection can show me that my resume, portfolio, or interview skills need improvement. The event itself is not fully in my control, but the meaning I ascribe to it is. That is where my power is.
   

4. Part 2 Action: Part two discusses taking action to overcome obstacles instead of only thinking about them. Ryan Holiday explains that persistence is not just blindly trying the same thing again and again; it means improving, adapting, and finding a smarter way forward. He says we should learn to use obstacles against themselves. In this section, he also discusses the idea of a “flank attack,” which means looking at the problem from a different angle instead of attacking it directly. Even when things fail, we should expect setbacks and keep moving forward.

   
   

   The best example I can provide is from learning tennis. If I keep losing points because my opponent has a stronger forehand, hitting directly to that side again and again would be foolish. Instead, I can use a flank attack by changing the direction, hitting to their backhand, using drop shots, or making them move forward and backward. The obstacle is still there, but I am no longer fighting it in the most obvious way. I am adapting my action until I discover a way to win the point.

   Furthermore, to use an obstacle against itself means that instead of fighting the problem directly, we use the energy, pressure, or limitation created by the obstacle to move forward. For example, if someone keeps criticizing my work, I can treat that criticism as free feedback instead of an insult. The obstacle is the criticism, but I use it to improve my writing, fix weak points, and become harder to ignore. In this way, the obstacle becomes the tool that helps me grow.
   

5. Part 3: Will. Will is the discipline of staying steady when the obstacle cannot be immediately changed. Perception helps you see clearly. Action helps you move. But Will is what keeps you from breaking when things are slow, unfair, painful, or outside your control. Abraham Lincoln is a strong example of perseverance because his life was full of repeated failures, losses, and setbacks, but he kept going.

   
   

   He lost elections, failed in business, faced deep personal grief, and still continued to work toward his purpose. Even during the Civil War, when the country was divided and people criticized him heavily, he stayed committed to preserving the Union and ending slavery.

   
   

   Lincoln shows that perseverance is not about never failing. It is about refusing to quit when failure, pressure, and doubt keep showing up. Moreover, the author also talks about building your own citadel, which is a stoic principle. To build your inner citadel is to develop a private strength within yourself: a place of reason, discipline, and self-respect that remains steady no matter what happens outside. It is not about becoming emotionless but about not becoming a slave to emotion. The world may shake your circumstances, but it should not easily shake your character. This part also talks about accepting your fate and anticipating everything that can go wrong with our plan.
   

Where I disagree:

The book wraps stoic philosophy as self-help, which feels like a wrong interpretation of the stoic texts. Furthermore, it is slightly repetitive because of how some chapters are related to each other. It can also be improved by giving examples of stoicism-practicing people in the modern age.

How I’m applying it:

I am applying it in my life by changing my perception of things to neutral meaning, taking action to fight obstacles, and learning perseverance. This book can be applied to all parts of our lives, be it sports, jobs, or relationships. I am trying to use this stoic knowledge every day.

Who should read this book:

If you are having a tough time or are at rock bottom, then this book might help you persevere or even flip your hardship and problem to success if applied daily. I also recommend this self-help book to people who are curious about stoic philosophy.