Ryan Holiday is a marketing guru, student of the stoics, rancher, and from all the podcasts, content, and books I’ve read of his, a pretty grounded family man. I just finished his latest book, Stillness Is The Key, this past week and wanted to highlight some of the learnings… it’s not a business book per se, more along the lines of self-improvement. Still, it is applicable to entrepreneurs and high-level athletes.
“All profound things, and emotion of things are preceded and attended by silence… Silence is the general consecration of the universe.”
– Herman Melville
A good friend and fellow entrepreneur gifted Holiday’s latest book. We’ve known each other for decades, and he knows I’m a checklist kind of entrepreneur who measures my days based on what was completed that day. As he’s reminded me over the years, and I don’t disagree, my need to complete checklists is a blessing and a curse. It’s a blessing because I tend to get shit done on schedule. It’s a curse because my checklists are lengthy every day. Until everything on that list is complete, my mind is occupied. That sometimes leads to rushing through daily tasks so to get to the next one, and missing opportunities… it can take the joy out of the process. And, inevitably, when joy is removed from the process, the quality of work will fade. Holiday addresses this very issue throughout his latest book.
Stillness Is The Key really sets the tone on how to perform at a high-level over the long-term while keeping a ‘life focus’… by that, I mean, it reminds us to get out of our own heads and stop over analyzing so we can live fuller, more present lives as leaders, parents, and friends. The book also focuses on the importance of routinely making time for solitude so to better understand ourselves, and maximize the prize of tranquility — something most people never discover.
The book will resonate with a wide audience because Holiday takes examples of what to do and not to do, from histories top performers. There are chapters dedicated to John F. Kennedy, Michael Jordan, Winston Churchill, Shawn Green, Tiger Woods, Seneca, and more.
Holiday highlights what these leaders were great at, of course, but he balances it with the other end of the spectrum. He explains how their mindsets, in some instances, drove them to anger, selfishness, and other less desirable traits.
Holiday explains to readers the dangers of making it to the top so to help recalibrate their mind and not fall into certain success traps. He doesn’t do this to bash success. Not at all. Rather, Holiday uses these examples of great success, so we learn to enjoy our time at the pinnacle.
And further to that point, he also reminds us of the power of forgetting! A strange but incredible concept as he urges everyone to “drop the old story.”
I’m going to highlight two of the lessons in the book. Hopefully, they encourage you to pick up a copy. There are nuggets of gold for every entrepreneur in Stillness Is The Key.
I’ll be honest… I’ve always bought into the philosophy that working harder than everyone else, every day, is a key to success. It was engrained in me from a young age, particularly as I became more competitive with sports.
I’ve clung to this mantra throughout my roughly 15 years as an entrepreneur. It worked well in my twenties. I had no other advantages over the competition other than the fact I was willing to work all day and night, sleep for a few hours, and do it all again the next day. It served me well, at least I think it did, for that period.
However, that pace is unsustainable and not optimal, particularly as I approach forty with two children and a wife… nor is it a desirable life to live over the long-term.
That pace can crush one’s ability to win under pressure when they need to be at their best. Being tired and robotic (consequences of going all out every day), won’t help when you’re in a stressful situation that demands peak performance.
Holiday uses the example of a world-renowned distance runner. He never practiced at full output, opting instead to train at roughly 80% effort. The world-famous distance runner trained like this so to avoid injury, increase longevity, and ensure he had a full tank of gas when it mattered most: during competition.
Shawn Green was a very successful professional baseball player. I remember watching him on TV when he played for the Toronto Blue Jays. He was the kind of baseball player who could field, run, and hit — and he could hit for power.
What I didn’t realize was Green went through a period that crushed his confidence — a hitting slump of epic proportions, which took a significant toll on his psyche/confidence.
As the slump lengthened, Green started overthinking all the little details of hitting. He would replay what he did wrong, and their potential consequences, in his head over and over (there are many aspects to hitting a baseball travelling at 90mph. It’s one of the hardest things to do in all of sport).
As the slump persisted, Green started worrying about his contract, his future as a professional, and his purpose. His overthinking and anxiety grew by the day, steepening the slump and threatening much of what he worked his entire life for. There was a genuine possibility he was headed for the minor leagues… or worse.
Thankfully, Green eventually made a breakthrough, and it had little to do with the mechanics of swinging a bat at a ball. In fact, it wasn’t even really about baseball. Green practiced Buddhism.
Holiday wrote, “It seems crazy, but it isn’t. “Man is a thinking reed,” D.T. Suzuki, one of the early popularizers of Buddhism in the West, once said, “but his great works are done when he is not calculating and thinking. ‘Childlikeness’ has to be restored with long years of training in the art of self-forgetfulness. When this is attained, man thinks yet he does not think.”
Holiday explained that the way out of the hitting slump for Green was to not think about much at all. Holiday wrote, “Instead, he repeated an old Zen proverb to himself: Chop wood, carry water. Chop wood, carry water. Chop wood, carry water.
Don’t overanalyze. Do the work. Don’t think. Hit.”
Green went back to the basics when practicing in the batting cage. He’d clear his mind completely. Plant his feet. Step into the pitch, let ‘er rip. Plant feet. Step into the pitch, let ‘er rip.
The slump ended with Green hitting homers, doubles, and singles galore. “No pressure. Just presence. Just happy to be there,” Holiday explained of Green’s new mindset.
These are just two of the valuable stories in Ryan Holiday’s Stillness Is The Key. The book reminds us how our mind and soul benefit from both success and failure while encouraging us not to overthink any single event or result. Every one of our experiences in life and business is educational, but none define who we are, unless our mind lets them. Furthermore, this book drives home, better than any, just how important it is to not rush on to the next thing — whether you’re winning or losing.
Subscribe to my newsletter for entrepreneurs and investors below. Only my best content will land in your inbox.