6 Life Lessons from The Obstacle Is The Way – by Ryan Holiday

the obstacle is the way

Ryan Holiday’s The Obstable Is The Way is the very first book that I read on the topic of stocism, an ancient Greek philosophy that emphasizes on the importance of not reacting emotionally to bad things that happen to you. Since reading this book, I have watched a lot of videos and listened to a lot of podcasts on the topic of stocism. Tim Ferriss says it best. He said that stocism is a great framework to think and I can’t agree with that more after learning more and more about stoicism. I usually don’t repeat reading a book right after I have finished it, but this one is the rare exception. Indeed, I have listened to the audiobook version of this book for at list ten times within the first three months of first reading this book. I simply love how it makes me think, calm down and learn while I take my long walk, listening to the book. There are so many important life changing lessons from the book. I will freely jog down the ones that stick to my mind and write down some of my reflections on them.

Keep Your Emotion at the Middle

In the book, Holiday called it “steady your nerve”. He mentioned that when something bad happens, if you keep your emotion steady, it may not even make you feel bad. Before you can get to the level of thinking that can turn obstacles into ways or lessons for learning, the first thing that you must learn is to not get emotional about bad things that happen. That also reminds me of the core concept of meditation or mindfulness practice that suggests us to let our thoughts flow by like clouds. Mingyur Rinpoche who is a meditation master put that as saying hi to your thoughts in your monkey mind when you meditate. Don’t judge the thoughts or the feelings. Let them fly by.

Know What You Can Control and What You Can’t

To keep your emotional at the middle, you have to understand what you can control and what you can’t. What you can control are basically our own actions, you have no control on what other people do or think. You also have no way to alter how the nature or the world works. If you understand something bad is outside our control, just tell yourself, “why bother feeling bad if there is nothing you can do about it”. So, the next time you get mistreated or misunderstood by a coworker, instead of getting mad, you can explain to him or her the situation so that you can be treated fairly. That’s the part that you can control. If he or she chooses to continue to mistreat you, don’t get emotional about it as that is outside your control. You have already done your parts.

Create Other Angles to Look at the Same Thing

The most important concept of book is of course how to turn an obstacle into a way. When I think about this concept more and more, it is so amazing to me how Marcus Aurelius, the stoic philosopher who was born in 121 AD already have written about the growth mindset concept, something the modern psychologist Carol Dweck has talked about in her bestselling book, Mindset. Whether you call it the growth mindset or using impediment to action to advance action as Aurelius put it, it basically means to find a perspective to turn something bad that happens to you into a lesson, a plan B, or simply a chance to practice virtues.

Here is an example of how I use this concept to stay calm during a recent event that was supposed to make me slightly angry and disappointed. I was talking to a potential client a few months ago. He was asking a lot of interview questions without really allowing me to fully explain my answers. He didn’t even give me a good chance to understand what his project is like, so he was basically just investigating whether I was good or not instead of making that meeting an opportunity to find out whether I was a good fit for the job or not. He was also speaking in a very cold and arrogant way. Eventually, I didn’t get the job. I was initially feeling angry and disappointed because I feel I was supposed to get a little more respect. I knew that from my past experience that it may take me hours to get rid of the useless thoughts. So I created two new perspectives in my mind to try to free myself from the bad thoughts. One, it is great that I didn’t get this job or I would possibly be working with pain due to how bad the client and I were able to communicate. Two, if this guy just happens to be an idiot who was just born rich, why would it matter to me whether he respected me or not. So, in a few minutes, I got rid of my bad feelings. And the very important lesson I learnt is that not getting a mismatch jog can save me a lot of time and suffering.

There is a Split Second Between Seeing and Reacting

Understanding that there is a split second to control and change how to react to anything is very helpful to me. The more I am aware of this, the better I learn to control my emotions. Sometimes, your life is filled with silly small things that can get you angry. For example, how would you feel if you waited fifteen minutes for your coffee and they end up giving you the wrong flavor? Even worse, they added cream to it when you are on diet. I don’t know about you but I used to get angry about silly things like this all the time. Once I get angry, I will not become productive again until may be a few hours later. After learning from this book, I can usually get rid of my angry thoughts within minutes, if not seconds. I almost feel like this is a new superpower taught to me.

Don’t Get Too High Either

Getting too excited about things can be as harmful as getting depressed. For example, I can also stop being productive when I get too excited. After practicing stocism more and more, I found that I have confused excitement with happiness my whole life. I now feel that happiness is that warm and poise feeling that comes from keeping my emotion at the middle and being able to see things with very clear eyes without filters.

Focus on the Process: One Clean Move After Another One is The Best Way to Execute

One of the emotions that can really stop you from reaching your goal is your fear towards the future, which is something that is unavoidably uncertain. It is a good thing to know your ultimate goal and then figure out the steps to reach it, but it is the worst thing to feel feared and stuck due to focusing on the difficult-to-reach goal all the time. Just like playing basketball, you should focus on one possession at a time and that will give you your best chance to win the game. Guarantee doesn’t exist. Best odd is what you are looking for.

This book has really opened a new door for me and it certainly is one of the most impactful books that I have read in my whole life. I really want to thank Ryan Holiday for writing such a great book that presents the stoic philosophy in such a beautiful and easy-to-understand way.