Book Reflections: Obstacle Is the Way

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Just some Random Book Notes from Obstacle is the Way

I just finished listening to the audio book “The Obstacle is the Way” by Ryan Holiday. I enjoyed the fact that I finished it over the past few days in Prague. Just helps me solidify what I learned. Taking long walks in new places and beautiful parks has been epic.

Another great way to learn about a book is to write up notes that you learned while going through it. So today I’ll write up some of my takeaways on the book, hope it helps you out.

Living a Life Of Stoicism

Ryan Holiday and Tim Ferriss are big believers of Stoicism, and through the podcasts and other books, they have convinced me to give it a try. The main idea of stoicism is to accept life for what it is. To live in the present. To accept the things that you cannot change and to enjoy and do the best with the opportunities you have.

That is how Ryan themes this entire book, The Obstacle in the Way. He mentions how great leaders throughout history have using stoicism readings to deal with massive amounts of stress and pressure.

The top 3 stoic writers he mentions are

Marcus Aurelius (his journal that became a book, Mediations of Marcus Aurelius)

I’ve actually gone through both of the first 2, in audio book form. They’re quite cool to listen to, as they have a narrator who speaks as if it was the Roman times again.

Finding obstacles means going right direction

If we don’t find obstacles, then we are living a life that is quite boring and standard. In order to make great changes on the world, we need to go where others have not gone. To face unknowns. To go down paths that are not yet blazed.

That means it will be hard. But we need to think positive. We need to expect these obstacles and realize that they are signals of growth and expansion.

Success means more obstacles

This is one that I always kind of have issues with. I used to always think “once I finish this hard task, things will get easier”. Or “I’m almost done”.


You are never done. And it will not get easier.

If you are successful, it only means more obstacles and challenges. That is the nature of the game. So don’t expect things to smooth out and get easy later. That is what I used to do, and it would set me up for failure. Or it would set me up to always get frustrated when there was another challenge (obstacle) on the next “level” of life.

So for me, now I just accept the fact that if I am going to make a difference in this world, I will face challenges.

I have to say, this is what happened with my China experience. When I first came, I thought I could “change it”. Then I got frustrated (like many foreigners) and took some time away. But coming back in 2011 (after some time back and forth between Philippines, China, and Hong Kong) I had no excuses. I knew what I was getting myself into.

Had a great sales campaign? Great, that means you will have to face a lot of order fulfillment and manufacturing headaches. It will not get easier until you are laying in your deathbed. Or if you give up and settle for a life that is not one you are meant for.

We should all have obstacles, and that shows we are growing and pursuing greatness.

Don’t Like Obstacles?

Not sure who does like obstacles. But we should try to flip it upside down and look at an obstacle as an opportunity. There is that saying I often say over and over in my head:

If it was easy, everyone would do it.

Because there is this obstacle, it makes getting past it that much more rewarding. If we always got whatever we wanted, without any obstacles, we wouldn’t appreciate it.

Ryan even goes to say that this is almost like hell, to get whatever we want without a challenge. He even hints towards that with his early success as an author. Now “what is next” for him. What is his next obstacle – as he achieved his lifelong goal so early in life.

He is seeking out obstacles. That is what we should do. This is how we are able to find opportunities and do things others have not yet done.

Today’s Generation Feels Entitled

Another one that was reflected a lot in the book is the sense of entitlement our current generation has. We all need a college education. And after college, we all should immediately get a job.

If we don’t get a job after college, it isn’t our fault – its our college’s fault. Or it is society’s fault. Never our own fault.

Especially with government, we always blame the government for not allowing us to do something. Blame our parents. Blame our friends. Blame the fact we were born in the family we were born in. That others have a better opportunity because they had money, or they have a different color skin than us. Always blaming others for their own situation.

We need to get past this, accept that life is what it is, we are born the way that we are – and that it is solely our responsibility to deal with it and get on with our lives.

Give The Obstacle in the Way a Try

This book has been recommended to me quite a few times. And they were all right. It is a mindset book, one that anyone trying to do anything “special” in their life should read.

It is mindset, it is attitude. It is accepting that if we want to do something meaningful – we need to accept the fact there will be obstacles – LOTS of them. And that if we are going in the right direction, even more obstacles after that.

So keep pushing forward – and you will achieve success. Just don’t accept there to be a smooth ride without a lot of speed bumps.

Read this book and motivate yourself – and join the others who face obstacles with a positive attitude.

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