My 7 Takeaways from The Obstacle is the Way by Ryan Holiday

What Stands in the Way Becomes the Way

I love non-fiction books that hit you with one powerful concept. Good examples are Extreme Ownership by Jocko Willink, Deep Work (my takeaways here) and Digital Minimalism by Cal Newport, Atomic Habits by James Clear, and Essentialism by Greg McKeown (my takeaways here). The structure typically involves the explanation of a specific challenge in our lives, clarification of the central concept of the book which is intended to help us deal with the said challenge, and then (if it is a good book) a framework for the application of the concept in practice, preferably with examples.

Ryan Holiday’s The Obstacle is the Way is one such book. In fact, the central idea of the book might just be one of the most powerful concepts I have ever come across. It can be truly life-changing. It is the basis of the philosophy of stoicism, but beyond that, it is an excellent framework on which to base your life, decisions, and choices, especially when dealing with adversity.

The impediment to action advances action. What stands in the way becomes the way. Marcus Aurelius

Not intuitive, right? At least not immediately. What stands in the way, becomes the way. This is not just a simple — if I see a wall, I’ll beat my head against it until I break through it — kind of a thing. It is not about stubbornly pushing through no matter what. It is not about ignoring all signs and evidence that a change in approach is needed.

Rather, it is about embracing challenges. It is about looking at what is to be gained from a challenge, rather than being depressed at the first sight of trouble or maintaining course no matter what. It is perhaps the most powerful example of REFRAMING, which is not only the key tool in terms of self-help and personal growth but also a powerful element of cognitive and mental health therapy.

Before diving into my takeaways from the book, briefly about who is Ryan Holiday. Author of several books about stoicism, Holiday is partially responsible for the growing interest in this ancient brand of philosophy. Holiday has hit the nerve with his books — there is clearly a demand for a way to help us navigate today’s stressful environment, at our jobs, businesses, and personal lives. Stoicism offers a useful framework for that. John Stuart Mill called Stoicism “the highest ethical product of the ancient mind”. Tim Ferris called it “a no-nonsense system designed to produce dramatic real-world effects. Think of it as an ideal operating system for thriving in high-stress environments.” High praise indeed.

Life is a trial. Or rather series of trials. We can choose to go through our lives drifting, or we can choose a method to help us deal with whatever life throws at us. Stoicism is one such method.

Ryan Holiday’s books The Obstacle is the Way, Ego is the Enemy, Stillness is the Key, Courage is Calling and the latest, Discipline is Destiny each takes a stoic concept and break it down with excellent examples to illustrate different aspects of this belief system. His Daily Stoic offers a daily one-page topic for reflection and meditation. His Stoic Diary is a journal with daily prompts, I have been using the Spanish version of it for almost a year — and I am planning to continue using it for reflection, meditation as well as for language learning. Finally, in his Lives of the Stoics, Holiday explores a different angle of educating us on stoicism, through the examination of the lives of prominent stoics, including Zeno, Epictetus, Seneca, and Marcus Aurelius.

Here are my 7 takeaways from The Obstacle is the Way by Ryan Holiday:

1. Grace. Poise. Composure. When facing an obstacle, the ability to steady your nerves, to maintain composure, is the first defense mechanism of stoics. As opposed to primal human reactions of fear, panic, anger, frustration, and so on. With grace, pose and composure, we allow ourselves mental space to start applying the skills to handle the situation we are facing. Holiday explains: “Don’t think for a second that grace and poise and serenity are the soft attributes of some aristocrat. Ultimately, nerve is a matter of defiance and control”. As Nassim Nicholas Taleb puts it, real strength is about the domestication of one’s emotions, not pretending they don’t exist. In my last jiu-jitsu tournament, I faced an opponent who came at me as a hurricane, I was surprised and overwhelmed, but focused on maintaining my composure. I practiced for this — I told myself. Only with composure, you can fight back. Stoics have a concept of an “Inner Citadel”, which means strengthening ourselves physically and mentally during good times so we are ready for the bad times. And when the bad times hit us, think as Lincoln did: “This too shall pass”.
2. Change your Perspective. I loved the story Holiday shares about the Athenian general Pericles. During a naval mission, a solar eclipse takes place and his men panic. Pericles takes a cloak off of one of his men and holds it up around his head. He then asks the man if he is scared of the darkness caused by his cloak. No, the man responds. Then does it matter what causes the darkness? Perspective is the key. As Marcus Aurelius put it: “Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been”. See the situation as it is, without panic, without the monsters that you think are lurking around. Stay objective. Miyamoto Musashi, a 17th-century Japanese swordsman, and philosopher highlighted the difference between observing and perceiving. The perceiving eye is weak, he writes; the observing eye is strong. The perceiving eye sees more than what is there. So after composure, comes perception. Only with the right perception, you can take the necessary action. Perception precedes action.
3. Changing our relationship with failures. I like this quote by Holiday: “Failure shows us the way — by showing us what isn’t the way.” Think Tomas Edison who in response to a question about his mistakes said, “I have not failed 10,000 times — I’ve successfully found 10,000 ways that will not work”. If improvement and moving forward is what we are after, failure (or most likely many failures) will be necessary. Failure is an asset if you are trying to get better or learn. As we try things, we will fail. Our level of comfort with failure is a big factor in how fast we are going to move forward. Think as start-ups think — fail and improve, fail and improve. Learning is never free — as Holiday puts it, the tuition is the discomfort of failure and having to try again. Think of failure as feedback.
4. Build resilience, or better yet, be Anti-Fragile. That which does not kill me makes me stronger. This is what is referred to as adversarial or post-traumatic growth. I will not elaborate on the concept of Anti-Fragility here, refer to Nassim Nicolas Taleb’s book on the subject. Essentially, the question is, what story do you tell yourself? The one of victimhood or empowerment? To help us approach adversity in such a way that moves us towards the latter, rather than the former, Holiday’s Obstacle is the way does not only describe the necessary perspective, attitudes, and actions but is also a depository of practical exercises. Instead of catastrophizing (read here), try imagining that what happened to you has happened to someone else. What would you advise that person to do? Or try the practice of pre-mortems — brainstorming about what can go wrong in your project and then plan what you would do in each one of these scenarios, however unlikely. This way you can anticipate failures and prepare for them. In life, things will go wrong. Or as per Murphy’s Law, “Anything that can go wrong will go wrong.” Or another version of this that goes “Anything that can go wrong will go wrong and at the worst possible time”.
5. Embrace the challenge. Amor fati — another Stoic concept that means love of fate. Welcome the challenge. Be glad to pay the cost. Find the opportunity in the obstacle. Embrace, because these obstacles are actually opportunities to test ourselves and try new things. Stop looking into the future of multiple possibilities. Focus on right now. Focus on what is in front of you. As Master Oogway from Kung-fu Panda says: “Quit, don’t quit. Noodles, don’t noodles… You are too concerned with what was and what will be. There’s a saying: Yesterday is history, tomorrow is a mystery, but today is a gift. That is why it is called the present.” Find what works best for you, whatever it is — hard exercise, meditation, time spent in nature, or music. A personal example — in my assignment in Sudan, my boss happened to be someone I had trouble connecting with. I was becoming more and more frustrated, but then I decided to treat this as a challenge — and over time, was able to figure out a way to build a constructive relationship. And that is how you can treat every challenge. Did you lose a document you worked on? Write it again, this time better. Your project did not get funding? You can improve your pitch. You lost a match? Analyze, identify the shortcomings in your game and be ready for the next match.
6. Action, Action, Action. As the German general Rommel put it: “Stay moving, always” or the modern version of it: Hustle! Thinking, planning, and discussing will not be enough. Action is the only way forward. As Holiday says: “Action is commonplace, right action is not”. So not just any action should do, but only deliberate, directed action. One step at a time, with incremental improvements, you make progress against your objectives and you overcome the obstacles you face. Act with courage and persistence. If you cannot influence something, if something is completely outside your control, fine. Live to fight another day. But if there is a chance, however slim, put 100% of the effort into it. As it is in jiu-jitsu, being pinned is just a position, not a fate. Something I like to tell my kids is — effort and developing skills do not guarantee success, but lack of effort and skill pretty much guarantees failure. Establish a process, routines, and trust in the work you put in. Track your progress. Finally, approach things as a craftsman, aiming to get better and better in whatever it is that you are trying to do — that is how you minimize your challenges and prepare yourself for them.
7. Handling pain and trauma. On this, perhaps the best thing you can do is to read Victor Frankl’s Man’s Search for Meaning (my takeaways here). Holiday touches upon how stoics handle the idea of death as the ultimate and insurmountable challenge. Memento mori. Meditate on your mortality. Anything less than death can be dealt with. Let me repeat the quote from Marcus Aurelius: “Choose not to be harmed — and you won’t feel harmed. As you go through life, it gets easier to do this. Think of life as a marathon, not a sprint. Think about all the people who came before us, who stood where we stand and experienced what we experience. Our pain and suffering are not unique. People have gone through this and have prospered. Not all, but some definitely have. And this thought should help you deal with the pain and suffering you are going through, however hard.

Here you go. To summarize:

“Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty”. — Ryan Holiday

So deal with your obstacle, welcome it, embrace it, learn and grow from it. And once you conquer your objective, as a Haitian proverb puts it: Behind mountains, there are more mountains. Or as Ariana Grande puts it (different context, but still works), “thank you, next”.