Lessons from Stillness is the Key by Ryan Holiday

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Stillness is the Key by Ryan Holiday is a book about inner peace and how this “stillness” is the key to “unlocking all that we are capable of in this life.” Holiday references ancient philosophers, religions, historical figures, and other successful people throughout the book to lay out his framework for achieving stillness: mastering the mind, spirit, and body.

I’ve been a long-time subscriber to Holiday’s monthly newsletter where he recommends books he’s read. It’s been a very helpful guide for the books I’ve chosen to read over the years and therefore, many of the people mentioned in this book felt very familiar: Ulysses S. Grant, Abraham Lincoln, Seneca, Tiger Woods, Winston Churchill, etc.

The following are some of themes from the book that resonated most with me the most.

Slow Down, Think Deeply

We have to get better at thinking, deliberately and intentionally, about the big questions. On the complicated things. On understanding what’s really going on with a person, or a situation, or with life itself.

We have to do the kind of thinking that 99 percent of the population is just not doing, and we have to stop doing the destructive thinking that they spend 99 percent of their time doing.

How much of our lives do we live on auto-pilot? I often catch myself scrolling my endless Twitter feed, reading random blog posts, refreshing my email inbox, and following conversations on various Slack channels.

The few moments when I’ve slowed down enough to contemplate big questions like “what do I really want out of life?” or “what are my values?” have always been fruitful, and yet, I tend to shy away from such deliberate thinking most of the time.

Start Journaling

How you journal is much less important than why you are doing it: To get something off your chest. To have quiet time with your thoughts. To clarify those thoughts. To separate the harmful from the insightful. There’s no right way or wrong way. The point is just to do it.

I’ve been journaling consistently since December 2016 (almost 3 years) and while most of my entries have been reflections on various things that happened the day prior, there are various themes and topics that I’ve been able to explore over the years.

Journaling has been one effective outlet for slowing down and thinking deeply although my sessions typically last anywhere from 5 to 20 minutes at most. However, I’m fairly happy that I’ve not been precious about the endeavor and kept it up, even as I’ve written some really repetitive and banal entries.

Find Confidence, Avoid Ego

Confident people know what matters. They know when to ignore other people’s opinions. They don’t boast or lie to get ahead (and then struggle to deliver). Confidence is the freedom to set your own standards and unshackle yourself from the need to prove yourself. A confident person doesn’t fear disagreement and doesn’t see change—swapping an incorrect opinion for a correct one—as an admission of inferiority.

Ego, on the other hand, is unsettled by doubts, afflicted by hubris, exposed by its own boasting and posturing. And yet it will not probe itself—or allow itself to be probed—because it knows what might be found.

I’ve often felt like I straddle a fine line between confidence and doubt. There are moments when I feel like no matter how hard I try, the results are lackluster and I just don’t know the answers. In these moments, my confidence wilts and I wonder if I should just give up.

But there’s another part of me that tells me that persistence is one of my key features and that steadily coming back with a different approach (while taking inputs from lessons learned or from people who know better) will eventually lead to a breakthrough. It’s from this that I often draw my confidence and go at it again. In the short-term, it feels like the act of digging a huge tunnel with a small chisel, but do it for long enough and the hole will emerge.

There are going to be setbacks in life. Even a master or a genius will experience a period of inadequacy when they attempt to learn new skills or explore new domains. Confidence is what determines whether this will be a source of anguish or an enjoyable challenge. If you’re miserable every time things are not going your way, if you cannot enjoy it when things are going your way because you undermine it with doubts and insecurity, life will be hell.

In running my own business, the entire enterprise has, at times, felt like an endless series of setbacks. Every day, new problems arise and I’m made aware acutely of the various inadequacies of our firm. Luckily, we’ve done a decent job of turning this circumstance into a culture of continual growth and learning–there are new lessons imparted on us every day and new opportunities to turn setbacks into valuable data points for subsequent actions.

Let Go

Mastering our mental domain—as paradoxical as it might seem—requires us to step back from the rigidity of the word “mastery.” We’ll get the stillness we need if we focus on the individual steps, if we embrace the process, and give up chasing. We’ll think better if we aren’t thinking so hard.

Holiday writes that being too outcome-focused get in the way of performance. It brings tension and stress in situations when a clear mind would be more helpful.

I sometimes find myself caught in this trap when I have a new business meeting with a prospect or when I’m interviewing new candidates. The wishful thinking of a good outcome often causes anxiety and it takes me a while to loosen up.

Exercise has been really helpful for cultivating the art of letting go. For example, if I think too hard about completing a tough lifting workout or a 6-mile run, I know it’ll cause a feeling of dread. However, if I focus on the individual steps (e.g. one rep at a time when lifting or literally one step in front of the other when running) and dive right into it, I’m a lot looser and able to get through without much worry.

Choose Virtue

If the concept of “virtue” seems a bit stuffy to you, consider the evidence that a virtuous life is worthwhile for its own sake. No one has less serenity than the person who does not know what is right or wrong. No one is more exhausted than the person who, because they lack a moral code, must belabor every decision and consider every temptation. No one feels worse about themselves than the cheater or the liar, even if—often especially if—they are showered with rewards for their cheating and lying. Life is meaningless to the person who decides their choices have no meaning.

Each of us must cultivate a moral code, a higher standard that we love almost more than life itself. Each of us must sit down and ask: What’s important to me? What would I rather die for than betray? How am I going to live and why?

This goes hand in hand with the ability to slow down and think deeply. I don’t think I’ve given enough thought to virtue in my life. I’ve assumed that being nice to people, taking care of my family, obeying the law, and living a normal life would be enough, but is it?


There is no stillness for the person who cannot appreciate things as they are, particularly when that person has objectively done so much. The creep of more, more, more is like a hydra. Satisfy one—lop it off the bucket list—and two more grow in its place.

You will never feel okay by way of external accomplishments. Enough comes from the inside. It comes from stepping off the train. From seeing what you already have, what you’ve always had. If a person can do that, they are richer than any billionaire, more powerful than any sovereign.

What do we want more of in life? That’s the question. It’s not accomplishments. It’s not popularity. It’s moments when we feel like we are enough. More presence. More clarity. More insight. More truth. More stillness.

This section of the book probably resonated the most for me. A big part of why I started and continue to run Barrel is a driving ambition to build something significant. Something that will impress others, something that will make me proud, and something that can be deemed a “success”. But to what end? When will it be enough?

I’ve been contemplating various aspects of this theme in the past year. Sure, there are financial and social rewards to reap with greater business success, but are they all that important?

Gratitude is a big component in appreciating that I have enough. While there are many more things I’d like to accomplish, I’m at the same time incredibly grateful for all that I’ve been able to do, experience, and enjoy in this life. That and the fact that I don’t need external validation to feel worthy or important. What matters is (as Warren Buffett talks about) my Inner Scorecard and knowing that I’ve tried my best in accordance with my value system.

Enter Relationships

Life without relationships, focused solely on accomplishment, is empty and meaningless (in addition to being precarious and fragile). A life solely about work and doing is terribly out of balance; indeed, it requires constant motion and busyness to keep from falling apart.

The writer Philip Roth spoke proudly late in life about living alone and being responsible or committed to nothing but his own needs. He once told an interviewer that his lifestyle meant he could be always on call for his work, never having to wait for or on anyone but himself. “I’m like a doctor and it’s an emergency room,” he said. “And I’m the emergency.”

That may be just about the saddest thing a person has ever said without realizing it.

This has become truer than ever for me as a parent. No amount of accomplishment can outweigh my duty first and foremost as a caring parent. The same goes for my roles as husband, son, brother, relative, friend, and work colleague. Relationships are what we remember years after the glory of our accomplishments. They require effort and care, but great relationships bring out the best in us.

Conquer Your Anger

If history is any indication, leaders, artists, generals, and athletes who are driven primarily by anger not only tend to fail over a long enough timeline, but they tend to be miserable even if they don’t.

Seneca’s argument was that anger ultimately blocks us from whatever goal we are trying to achieve. While it might temporarily help us achieve success in our chosen field, in the long run it is destructive. How excellent is excellence if it doesn’t make us feel content, happy, fulfilled?

Anger is counterproductive. The flash of rage here, an outburst at the incompetence around us there—this may generate a moment of raw motivation or even a feeling of relief, but we rarely tally up the frustration they cause down the road. Even if we apologize or the good we do outweighs the harm, damage remains—and consequences follow. The person we yelled at is now an enemy. The drawer we broke in a fit is now a constant annoyance. The high blood pressure, the overworked heart, inching us closer to the attack that will put us in the hospital or the grave.

Anger has no upside. I was foolishly angry about many things in my teens and twenties. I’ve mellowed out some in my thirties, and I hope to continue developing a hold over my emotions, especially in tense and delicate moments.

All is One

No one is alone, in suffering or in joy. Down the street, across the ocean, in another language, someone else is experiencing nearly the exact same thing. It has always been and always will be thus.

We are all strands in a long rope that stretches back countless generations and ties together every person in every country on every continent. We are all thinking and feeling the same things, we are all made of and motivated by the same things. We are all stardust. And no one needs this understanding more than the ambitious or the creative, since they live so much in their own heads and in their own bubble.

Finding the universal in the personal, and the personal in the universal, is not only the secret to art and leadership and even entrepreneurship, it is the secret to centering oneself. It both turns down the volume of noise in the world and tunes one in to the quiet wavelength of wisdom that sages and philosophers have long been on.

I interpreted this section as being about perspective. If we pull back far enough, we are but a speck in the universe. If we zoom in enough, we are the same particles. And when you look at it through the lens of time, we are here but for a blink of an eye.

There are so many forces in today’s modern world working to divide, segment, and sensationalize how we experience the world and relate to each other. When we pause to realize that, as people, we’re not all that different, it’s an opportunity to develop empathy and fight back the forces that splinter us.

At a personal level, this means challenging myself to relate with people with different beliefs, different views of the world, and different life experiences. It’s been too easy to nestle in the cocoon of sameness.

Act Bravely

What is better? To live as a coward or to die a hero? To fall woefully short of what you know to be right or to fall in the line of duty? And which is more natural? To refuse a call from your fellow humans or to dive in bravely and help them when they need you? Stillness is not an excuse to withdraw from the affairs of the world. Quite the opposite—it’s a tool to let you do more good for more people.

A person who does good regularly will feel good. A person who contributes to their community will feel like they are a part of one. A person who puts their body to good use—volunteering, protecting, serving, standing up for—will not need to treat it like an amusement park to get some thrills.

Marcus Aurelius spoke of moving from one unselfish action to another—“only there,” he said, can we find “delight and stillness.”

A good place to practice “doing good” is on the subway. Am I helping the old ladies at the Chinatown stop haul up their carts up the stairs? Am I giving up my seat mom with a young kid? Am I taking off my backpack and setting it on the floor to make room for others?

I’ve lived a mostly sheltered and safe life where the call for bravery has been non-existent. However, this doesn’t mean I can’t act bravely in my daily life. When I’m heads down on my phone and thinking only about where I have to go, I know I’m likely to be cowardly if anything will inconvenience me. This is why all the themes in this book connect with each other and allow for virtuous behavior – when you’re living in the present, when you have stillness in your life, you’re more likely to be in the right mind to act bravely, doing what’s right and good in service of others.

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