Book Report: Stillness is the Key

Full disclosure, I was already a fan of Ryan Holiday and his books on Stoicism, so it isn’t surprising that I enjoyed this one.

The bad news is that I am kind of mad about it.

Stoicism has become a recent focus for me. (Real Stoicism, not the bro version that is increasingly popular right now. Looking at you Jordan Peterson.) And the whole time I have been diving into it, there has been an odd thing I have noticed.

Parts of it felt familiar.

Not in the “This is a blatant rip off” kind of way, but just familiar.

Reading this book helped me figure out why.

It is somewhat difficult to train in martial arts for a long time and not become a bit of a philosopher. That grind of working on one technique or move over and over, the incessant need to refine them, it’s something that you eventually fall in love with.

You have to, otherwise, you quit. I have seen this happen time and time again.

My Kung Fu teacher is a bit of a scholar, and his teaching brought in a lot of Eastern philosophical ideas that he used to illustrate concepts and to help us understand the goal of any martial arts master: “love the process and not the results.”

He would sneak in little nuggets so that after, a couple of years, you are steeped in Eastern philosophy and not even aware of it. 

Poker is full of the same thoughts, they’re just applied differently. You can’t play the current hand well if you are still emotionally tilted (angry) about the last hand. 

Let. It. Go.

Also in poker—and in sales and every other aspect of life—you can do everything correctly in a hand and still lose.

Then, when I started to work with sales coaches and focus on improving my selling and communication skills, there was even more philosophy in there. I just couldn’t see it when I started. But a lot of the ideas that I learned and talk about so much comes from Eastern philosophy:

  • Focus only on what you can control.
  • Don’t build your value on getting a yes from someone else.
  • Focus on the inputs and processes that lead to the results.

Memories of getting a no from a client and then not feeling like I could walk into another office and face another one still haunt me. So much time wasted on fearing the worst and putting more energy into results that I couldn’t control. But that stopped when I started to look at sales differently.

It went even further when I started getting into Stoicism. It all really hit home when I realized that there was a lot of overlap between all of the things I’m passionate about. I was already getting excited about the idea that the same ideas are present in these different realms…..then Holiday comes along and does a better job than I could have hoped to tie these ideas together.

Normally, his books focus on just Stoicism, but in this book, he expands his view and talks about how all philosophies share a lot of the same ideas and take you to roughly the same place mentally. This book feels like it comes from a more mature, experienced point of view. I really enjoy Ego is the Enemy, and The Obstacle is the Way was huge for me, but I would recommend Stillness is the Key even more than any of the others.

The reason for that is that this book gives you everything you need to do to cultivate a mindset that serves you instead of being at the whim of every attention-seeking thing in your life.

So not only does the book do a better job of explaining a concept I was only beginning to understand, it shows you exactly how to start and what to do. Good game, Holiday.

The book is broken up into three main categories: Mind, Spirit, Body. I was going to focus on my favorite subsections, but honestly, I can’t. There is a lot of great information in each section of the book. And if you do what this book advocates, you will change (in my opinion) for the better.

Holiday’s usual approach of taking past and present figures from history and examining how philosophical ideas helped them navigate tricky situations is still in play here, but I found the people he chose to highlight in this one particularly interesting. 

He talks about Kennedy and the Bay of Pigs situation, Tiger Woods, Johnny Cash, Michael Jordan, and others. People who have had some very well known situations where their character was in question. People who have had situations that would have led to them being “canceled.” It feels intentional, and I am not at all mad about it.

Their moments of greatness don’t grant them a get-out-of-jail-free card. Go watch “The Last Dance” if you think it was all sunshine and rainbows being on the same team as Michael Jordan, let alone one of his competitors who he would do ANYTHING to have an edge over.

Being at the top of any game requires sacrifice. The examples in the book are names we all know and are familiar with and probably have some opinions about. They are not perfect, but that, to me, is the whole idea. That balance.

I have spent a lot of time doing things to try and improve various areas of my life since realizing that personal development was not all bullshit.  Many of the things that I have seen the most improvement from are the things Holiday suggests in this book. As someone who has made mountains of mistakes, still occasionally loses the ability to not sweat things that are outside of my control, who strives not to focus on the results or care what other people think, I found these examples to be comforting in their imperfection. 

Living a life focused on improving and learning, there are plenty of days where it feels like nothing has changed and I am still the same person I was at 20. I put a lot of self-imposed pressure to improve myself, and when I fall into an old mental trap, it can be hard to swallow. 

The examples in this book allowed me to take it slightly easier on myself.

Still is the Key will be especially great for people who are just entering into philosophy/personal improvement. Since there are a lot of different schools of thought referenced in this book, you can get a feel for different ideas and approaches so that you can find the path that suits you best.

If you find that path, supplement that reading with what this book talks about. You will have no choice but to end up in the same space as others in history who have walked a path towards that same destination.

My goal is to continue working on these ideas so that when you get there, we can hang out together and have the kinds of conversations that are only available when you put in the work of honing your mind.