I’ve never done a book review outside of school before. I’m 100% winging this and hoping that some structure will rise from the chaos of my ramblings. For some background I typically read some sort of self development book for 30 minutes to an hour each night before bed. These range from philosophy to business/entrepreneurship to psychology and more. I want to make it a practice of synthesizing what I read and distilling down the major points I take from each book.
I finished Ryan Holiday’s “The Obstacle is the Way” recently. It acts a general overview of the philosophy of Stoicism and conveys the teaching of Stoicism through real-world examples of people applying the principles of the practice in magnificent ways.
Overview
Holiday begins the book by explaining the overview of Stoicism as a 3 part philosophy:
- Perception
- Action
- Will
He then proceeds to break the book into these 3 sections and goes through each one.
Each chapter starts with a story of a historical figure accomplishing some task or overcoming some obstacle. It details their method and the attributes the person possessed that are in line with Stoicism. From Washington, to Edison, to Amelia Earhart, Holiday provides numerous examples of the ideas and teachings of Stoicism in action.
After the example is detailed and explained he then quickly breaks down the lesson to be learned and gives a simple overview of what you can do with the lesson in your life. Each individual example comprises a “chapter” and is typically 3-10 pages long.
Perception
In this section Holiday discusses how to alter and control your perception of events in order to be more objective and practical about the problems you are facing. He talks about embracing the power of being able to CHOOSE how you view your circumstances rather than be a victim to them. He discusses how to view problems as opportunities rather than obstacles (The Obstacle is the Way.) The first premise of Stoicism, as I understand it from this book, is that the way we choose to view the problems in our lives determines our response to those problems.
By viewing circumstances as opportunities and considering the problems in different contexts we gain control of our reactions to those problems. Holiday discusses how Stoics controlled their emotions and reactions by embracing rational, objective views of reality. Instead of reacting to circumstance automatically they would take time to analyze the problems in front of them, allowing them to be less rattled.
Action
This section is similarly comprised of major themes that run throughout. First, that persistence is key. Rather than giving up and walking away you face problems squarely and either crack them under the pressure of your persistent focus or use your perception to find a creative way around the obstacle.
The importance of “getting moving” is also discussed. Stoicism argues that moving in the right direction even in a way that is not ideal may be better than the alternative of letting yourself get stopped because you aren’t willing to compromise.
Ultimately the lessons from this section break down into persistence, creativity, and focus. Be persistent in trying to find solutions to problems. If your sheer unending assault on a problem does not solve it then direct that relentlessness in a creative new direction by trying different and unique solutions. Most importantly, staying focused on the goal and not getting caught up by the obstacles in the way. By letting the obstacle dominate our focus we lose sight of what we are trying to accomplish.
Will
This section discusses that the Will is the power we use to apply the lessons from Perception and Action. It reviewed concepts like perseverance, acquiescence, working towards goals greater than ourselves, and human mortality. The section conveyed the different sources and applications of the Will. For example, humans can derive Willpower from contemplating mortality, as consideration of death puts all of life and its troubles and problems into perspective.
The section also considers having a cause that is greater than ourselves in service to others. By taking ourselves out of the equation we are able to tolerate and resist a significantly larger amount of discomfort and obstacles. It’s no longer “I have to get through this” but “we have to get through this.”
My Thoughts
The book does a good job of providing examples of the application of Stoic philosophy. Each example is inspiring and powerful, and demonstrates the concept Holiday is trying to explain well. The heightened nature of each story allows the concept to be displayed very simply. Big events create big reactions, and the size of the events in each story allow the application of Stoicism to stand out dramatically.
This is a good thing for the sake of explaining the concepts. It makes them plain and obvious. Holiday uses each example to break down how Stoicism was applied in the scenario. The book does a good job of giving the reader an overview of Stoic thinking and shows how it can be used in the real world.
I had two major issues with the book however. First, the pacing. Each story and explanation is around 2-5 pages long. While the stories themselves were interesting and entertaining I found that the explanations behind them were conceptual more than practical. The length of each section being so short should be a blessing but reading the book felt disjointed to me. Perhaps I went into it expecting something different than it was.
My second issue with the book ties into the first. I think the pacing felt slow and disjointed because each explanation of the stories felt surface-level to me. It said “X person did this in the face of adversity, you can also do that.” This does not impact the quality of the book, but I think my frustration came from expecting something other than what I got.
Each chapter feels like the introduction to a book of its own. It explains the concept that will be discussed and shows some basic applications of the concept in order to hook you on the idea so it can be explained in detail. I read each chapter expecting the book to begin explaining the process of applying the information in a meaningful way. Each chapter would end with some general advice and then the next chapter would start. While the themes of each of the major 3 sections stayed consistent each chapter was self-contained and did not really build on the previous ones.
This made the book hard for me to read. I finished Tim Ferris’ “4 Hour Work Week” in about a week, it took me 9 days to finish the “Obstacle is the Way” because I would read one chapter, be disappointed that it did not discuss the concept more in depth, and then force myself to read another chapter or two for the sake of progress. Again, each chapter is only 2-5 pages typically, so I would make maybe 10 pages of progress a night. With 4HWW I finished the first two SECTIONS, each of which are larger than the totality of “The Obstacle is the Way,” in 2 days.
Again, I do not believe this is the fault of the author, the book is well-written and clearly thought out. I believe my lack of engagement came from not being experienced in reading philosophy and expecting something more like “Atomic Habits” by James Clear, step-by-step applications of the concepts being discussed.
(Upon editing this review I realized that I did end up taking a lot from the book. While I found it frustrating to read, I did enjoy the content. It gave me a new perspective on some things, adjusted my view on others, and generated interest in the topic of Stoicism)
I read a lot of self development books. I appreciate books that lay out a formula for change clearly and with step-by-step guidance. My background is in psychology, I enjoy material that is more practical than conceptual. It’s hard to quantify what exactly makes a book grab and keep my attention. I could understand all of the concepts discussed in Holiday’s book, and found that I had picked up some Stoicism along my own journey of self-mastery prior to ever reading anything about it. But while I could understand the concepts, it was difficult for me to truly grasp it in the sense that I understood how to apply each lesson into my own life.
Lessons
That being said, I did take some lessons from the book that I hope to begin incorporating into my own life:
First, I think the Perception section of the book was most relevant to me. When I am working towards something I feel is important I am pretty much unstoppable. Provided sufficient reason for doing something I don’t struggle with falling off the wagon so to speak. Perception however is something that I have fallen victim to for a long time.
The story that stood out to me the most in this section and maybe the whole book, was about George Clooney. The story details the beginning of Clooney’s acting career and the struggles he went through. Specifically, Clooney went into auditions hoping to meet the standard of the panel there to decide who got the part. His perception was trying to be good enough for THEM. After years of failures Clooney realized that just as much as he WANTED the parts, the people looking for actors NEEDED the actors. They HAD to fill those roles. Clooney changed his perception from one of trying to impress the judges to one in which he knew he was what they were looking for and presented it to them. Suddenly he begins getting roles that lead him to his fame and success.
This stuck out to me because I have struggled with the same things in different arenas of life. Despite all evidence to the contrary I would perceive that I was not good with people or didn’t fit in, and it would eventually become that way. I created self-fulfilling prophecies for myself. Practicing changing my perception of events and my view of myself is something that I will begin after reading this book.
The second lesson I took was in the Action section. I can’t point to one specific section because it was the theme throughout. The idea is that by manipulating our Perception of events we can come up with unique and creative solutions to problems. Rather than just trying one way, Holiday points out that the Stoics would consider many different solutions and be able to adjust to them. Rather than considering the obstacle as something impassible it was just creating a new path to follow. When you take up this belief that all setbacks, hardships, obstacles, and problems are just leading you in a new direction you begin to consider more creative solutions to problems.
Sometimes you need to let the problem solve itself, sometimes you try something completely different, sometimes you adjust slightly. Whatever the case may be, the important thing is to not consider the journey over simply because you were stopped momentarily. This idea is something I will discuss more in the next section.
The last lesson I took was at the very end of the book. Holiday discusses how every bad thing that happens in life is an opportunity to advance ourselves. This is the major theme of the entire book, but restating it right at the end really did tie together the message well. If I take one thing permanently from reading this book, it would be this final lesson of always viewing hardship as advantageous. It’s something I plan on practicing more of.
Takeaways
The purpose of this blog is to openly document my process of building my own philosophy/lifestyle/way of thinking so that eventually I can review this material and see the themes and patterns. I want to understand the “meta” of my thinking, the overarching strategy behind what I do, that way I can teach it to others. I put out these articles and reviews onto the internet so that others can one day see those patterns and hopefully learn how to learn better alongside me.
To that end, I think it is important to be up front about what I read and how I plan to use it. I did not enjoy reading The Obstacle is the Way. If you are looking for a user’s manual on how to use Stoicism in your own life this is not it. The Obstacle is the Way is a philosophy book. It gives you an overview of the concepts of Stoicism. It is an introduction.
I always keep a mental list of books and resources I would recommend to people if they were to ask me how to learn about specific topics or just get better at life in some way. If someone wanted to learn more about Stoicism and didn’t know where to start I would point them to this book. If someone wanted practical life advice I would point them elsewhere first.
I’ve detailed above some of the major takeaways that I will be practicing in my own life. I think it is important to note that while I was not engaged while reading through the Obstacle is the Way I did find myself interested in the topic of Stoicism. So much so that I found a compilation of Marcus Aurelius’ “Meditations,” Seneca’s “On The Happy Life,” and Epictetus’ “Enchiridion” and have purchased it to continue learning about Stoicism. If Holiday’s goal was to generate interest in Stoicism he succeeded wonderfully. My interest is piqued.
Lastly, I have written about this on Twitter briefly, but I have noticed as I continue to explore self mastery and read these different philosophies, religions, and ways of life, more and more trends emerge. I call it the Universal Truth, the idea that each philosopher or teacher who explores what it is to be human and how to live the best life possible are all working towards the same general ideas. I have no illusions that if a Universal Truth about humans exists I will not understand it in its entirety in my lifetime, and that’s not my goal.
My goal is to chip away as much as I can. My goal is to take in as many different concepts and build the best framework I can to create fulfillment and contentment within my life. My thinking on this is that the more I read and learn the more I see overlap. Those overlaps are hints at the Universal Truth.
For example, Stoicism speaks on accepting what is rather than getting upset and fighting against it. It teaches that we must accept our circumstances and not allow them to overwhelm us. This is a very similar concept to Taoist teachings. Taoists suggest that we must be like water, flowing effortlessly through life. A central tenant to Taoism is being able to accept what is and not concern ourselves with it. The Stoic idea of allowing the obstacles to show us the path is practically identical to the Taoist concept of Wu Wei, effortless action. Wu Wei teaches that we should wait until the universe (or Tao) opens the way for us and then be ready to take action when it is time. It’s a state of being content to relax and float along until the time is right to do something.
The point is, as I continue to explore these concepts I see more and more overlap. Psychology, Taoism, Stoicism, modern Self Development teachings, Buddhism, and so on. I am excited to continue reading about Stoicism and add it to the growing collection of things I have grafted onto my Frankenstein’s Monster of a life philosophy. IT’S ALIIIIIVE!!!!
You can purchase “The Obstacle is the Way” here.