Stillness is the Key – Book Notes and Summary

Stillness is the Key by Ryan Holiday

One-sentence summary: In Stillness is the Key, Ryan Holiday shares the secrets to cultivating the calm and inner fortitude necessary for any sustainably successful life.

Rating: 10/10

Author: Ryan Holiday

Date Completed: October 2019

Tags: Stoicism, Self-Knowledge, Psychology, Decision-Making, Life Strategy, View Quake, Anger, Ego, Bravery, Hobbies, FIRE, Relationships, Health, Happiness, Going to Clovis

Hot take: For my money, Stillness is the Key is the best book Ryan Holiday has ever written or will ever write. Everyone’s over the moon (or, if you’re a Stoic purist, deeply upset) about The Obstacle is the Way, and Ego is the Enemy, but this is the one that makes the trilogy worth it for the ambitious and achievement-obsessed among us.

Big Ideas

All the ancient schools of thought – Buddhists, Christians, Stoics, Epicureans, etc. – all spoke of stillness as one of their primary goals.

  • What is stillness? It’s a flow state where you’re at peace with yourself and present in the moment. Not worried about where you need to go next, but comfortable here and now.
  • It doesn’t necessarily mean being physically still. You could be walking down a quiet street at night or running through the park as the sun rises.
  • “You may be sure that you are at peace with yourself when no noise reaches you, when no word shakes you out of yourself, whether it be flattery or a threat, or merely an empty sound buzzing about you with unmeaning sin.” -Seneca
  • There are only a few areas of consensus in ancient wisdom, but, as Holiday writes, “When basically all the wisdom of the ancient world agrees on something, only a fool would decline to listen.”

Presence makes stillness possible.

  • You can’t feel stillness while scrolling on your phone or honking your car horn at another driver who’s in your way. Likewise, you can’t be present if you’re ruminating on the past or obsessing about the future. So if you hope to attain stillness, your first job is to find a way to be in the present moment. 
  • “Remember, there’s no greatness in the future. Or clarity. Or insight. Or happiness. Or peace. There is only this moment.”
  • “Who is so talented that they can afford to bring only part of themselves to bear on a problem or opportunity? Whose relationships are so strong that they can get away with not showing up? Who is so certain that they’ll get another moment that they can confidently skip over this one?”
  • “Don’t reject a difficult or boring moment because it is not exactly what you want. Don’t waste a beautiful moment because you are insecure or shy. Make what you can of what you have been given. Live what can be lived. That’s what excellence is. That’s what makes presence possible.”

Learning to have “enough” is the currency of a good life.

True story, Word of Honor:
Joseph Heller, an important and funny writer
now dead,
and I were at a party given by a billionaire
on Shelter Island.
I said, “Joe, how does it make you feel
to know that our host only yesterday
may have made more money
than your novel ‘Catch-22’
has earned in its entire history?”
And Joe said, “I’ve got something he can never have.”
And I said, “What on earth could that be, Joe?”
And Joe said, “The knowledge that I’ve got enough.”

-Kurt Vonnegut
  • Having enough money means you can let go of the pursuit of more, stop optimizing every decision for what will save you or make you the most money. Enough recognition will make you less of an attention hog at work, giving your team credit for their work to make you look successful. Enough pleasure means you won’t chase alcohol, drugs, sex, or food to provide another hit of dopamine.
  • Those who don’t learn that “enough” is the bedrock of happiness are doomed to suffer. One such example is Tiger Woods. His father pushed him to and beyond the human psyche’s limits in training him to be a world-class golfer. Their safe word beyond which Earl Woods would stop berating his son? “Enough.”
    • “Not only was it never uttered, but the two of them came to refer to it almost as an expletive: the ‘e-word.’ The e-word was something quitters said, that only losers believed in.”
    • This behavior drove Tiger to the top of the game – and then to the bottom as he crashed out his life on over-training, sex, and drugs.
    • “As he worked to crowd out the distractions – anything that would get in the way of his concentration addressing each shot – he was also crowding out so many other essential elements of life: An open heart. Meaningful relationships. Selflessness. Moderation. A sense of right and wrong.”
    • “Eventually one has to say the e-word, enough. Or the world says it for you.”
  • You’ll never feel better by achieving more external things if your inner world is in tatters. “Nothing is enough for the man to whom enough is too little.” -Epicurus
  • Or, as Holiday puts it: “If you believe there is ever some point where you will feel like you’ve ‘made it,’ when you’ll finally be good, you are in for an unpleasant surprise. Or worse, a sort of Sisyphean torture where just as that feeling appears to be within reach, the goal is moved just a little bit farther up the mountain and out of reach. 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.”
  • You might be thinking that, of course, a rich, successful author can preach about stillness and “enough” when he already has plenty, but what about the rest of us who are still climbing and don’t want to lose our edge? We need to stay hungry, and enough impedes that. Holiday has an answer: “No one does their best work driven by anxiety, and no one should be breeding insecurity in themselves so that they might keep making things. That is not industry, that is slavery.”
  • If you reach enough but love what you do, you won’t stop making things. But the things you do make will be more truthful. “No creeping, painful hope that this would finally be the thing that would make them feel whole, that would give them what they had always been lacking.”

Virtue is a path to stillness.

  • I’m not talking about sitting in the woods and meditating five hours a day or never hurting a cockroach, even if it’s sitting on your dinner plate. But knowing what your values are, who you are, and what you will and won’t do – is vital to achieving stillness.
  • Virtue can mean a lot of different things to different people. I think it means two things:
    • Taleb’s Silver Rule – don’t do anything to anyone that you wouldn’t want them to do to you.
    • Summum bonum – the Stoics used this term for the highest good for the greatest number. What’s good for the hive is good for the bee, etc.
  • “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.”
  • The gentleman is self-possessed and relaxed, while the petty man is perpetually full of worry.” -Confucius
  • That doesn’t mean that people who aren’t virtuous can’t take advantage of those who are and make their way to the top of their fields – for a little while. You can pursue this strategy, but it takes its toll on your self-image and your security at the top as well. Think Sammy Glick from What Makes Sammy Run?

Go outside. Remain.

  • “Beauty remains, even in misfortune. If you look for it, you discover more and more happiness and regain your balance.” -Laura Ingalls Wilder
  • That doesn’t mean you have to be in an objectively beautiful place – there’s plenty of beauty in ordinary things, even in things we didn’t want or don’t like.
  • Remember looking out your window on an early morning? What about steam rising from a sewer grate? These are all sources of beauty and stillness.
  • The Japanese have a practice – often medically prescribed – called shinrin yoku (“forest bathing”). It’s going outside into the woods and standing among the trees. My version is walking along the river in New York, watching the boats pass and the waves lap up against the concrete. Yours could be anything – taking the dog for a walk, running on a path near your house, etc.
  • The next time you’re feeling stressed or overprogrammed, stop. Go outside. “Marvel at the fact that any of this exists – that you exist.”
  • One of the best ways to do this is to take a walk, a practice that Holiday – and plenty of historical philosophers – undertook. Kierkegaard wrote, “Every day I walk myself into a state of well-being and walk away from every illness; I have walked myself into my best thoughts, and I know of no thought so burdensome that one cannot walk away from it.”

Relationships are a source of stillness in the storm.

  • The productivity porn cultists (including me, as a recovering productivity addict) believe that relationships slow you down. A partner is the death knell of creativity. According to Holiday (and reaffirmed by my practical experience), this couldn’t be further from the truth.
  • Instead of withdrawing, make yourself vulnerable to another person. Allow someone to know you. Make sure there are no secrets between the two of you. This isn’t a weakness – it’s strength.
  • “Relationships are not a productivity hack, though understanding that love and family is not incompatible with any career is a breakthrough.”
  • “It is also true that the single best decision you can make in life, professionally and personally, is to find a partner who complements and supports you and makes you better and for whom you do the same. Conversely, choosing partners and friends who do the opposite endangers both career and happiness.”
  • “The world hurls at us so many hurricanes. Those who have decided to go through existence as an island are the most exposed and the most ravaged by the storms and whirlwinds.”
  • Freud said that love is the great educator. We learn in the process of both giving and receiving love.
  • “To go through our days looking out for no one but ourselves? To think that we can or must do this all alone? To accrue mastery or genius, wealth or power, solely for our own benefit? What is the point? By ourselves, we are a fraction of what we can be. By ourselves, something is missing, and worse, we feel that in our bones. Which is why stillness requires other people; indeed, it is for other people.”

Embrace perspective to recognize how closely connected we all are. 

  • Think about something you love: a favorite team, a band, your family members, your most prized possession. Now try remembering that everyone in the world – and probably just about everyone who’s ever lived – feels that way about something. Even, as Holiday writes, the guy who just pushed you in the supermarket.
  • This reminds me of David Foster Wallace’s “This Is Water” speech. You could see ordinary moments as banal or frustrating – or you could see them as beautiful, meaningful, and “on fire with the same force that lit the stars.”
  • The moon is an example Holiday gives: the moon you stare at tonight is the same one you saw when you were a child, looking up in wonder at something you didn’t understand. It’s the same moon that all the significant figures of history have stared at in one moment or another. It’s the same one you’ll look up at when you’re old and grey. There’s a comforting oneness in all that. It centers you, both within yourself and in your place in the universe.
  • “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.”‘
  • This recognition almost definitionally has to bring us peace. The things we fight for and against are nearly the same, with shades of grey. “Peace is when we realize that victory and defeat are almost identical spots on one long spectrum.”

Get a hobby.

  • “The cultivation of a hobby and new forms of interest is therefore a policy of first importance to a public man. To be really happy and really safe, one ought to have at least two or three hobbies, and they must all be real.” -Winston Churchill
  • I tend to think of leisure as sitting on a lounge chair doing not much at all. That’s not the truest implementation of the historical practice, though, where leisure was the freedom from needing to work and spent doing interesting things for their own sake – usually intellectual pursuits.
  • “It’s a physical state – a physical action – that somehow replenishes and strengthens the soul. Leisure is not the absence of activity, it is activity. What is absent is any external justification – you can’t do leisure for pay, you can’t do it to impress people. You have to do it for you.”
  • That’s not to say leisure can have no practical benefits in your life, but that can’t be the point of it. If you’re doing a leisure activity to get better at your job, that isn’t leisure anymore.
  • Leisure also gives you a ready-made way to suck at something. “It’s the humility of being bad at something because we are a beginner, but having the confidence to trust in the process.”
  • “Life is about balance, not about swinging from one pole to the other. Too many people alternate between working and bingeing, on television, on food, on video games, on lying around wondering why they are bored.”
  • “There is nourishment in pursuits that have no purpose – that is their purpose.”

Embrace solitude.

  • Holiday writes that solitude allows you to reflect while others react. To avoid being just as reactive, you should seek out intentional alone time.
  • “It is difficult to think clearly in rooms filled with other people. It’s difficult to understand yourself if you are never by yourself. It’s difficult to have much in the way of clarity and insight if your life is a constant party and your home is a construction site.”
  • Some leaders have understood the value of solitude – like Churchill suggesting that “every prophet must be forced into the wilderness” and Bill Gates taking bi-annual “think weeks” in which he goes to a cabin in the forest for seven days, by himself reading and writing.
  • “Breakthroughs seem to happen with stunning regularity in the shower or on a long hike. Where don’t they happen? Shouting to be heard in a bar. Three hours into a television binge. Nobody realizes just how much they love someone while they’re booking back-to-back-to-back meetings.”

Build a routine. 

  • You might think that doing the same thing every day is dull or that it limits your creativity. According to Holiday (who echoes a sentiment from Austin Kleon’s Steal Like an Artist here), a routine is an excellent source of stillness as well as a platform to do your best work. 
  • A day where nothing is routine is a day filled with exhausting decisions. You have to choose what to eat, what to wear, what to do, what to pay attention to, who to spend time with, what to watch, and when to go to sleep. A day with that many decisions is subject to “conflicting impulses, incentives, inclinations, and external interruptions.” It’s tough to imagine feeling calm and centered with so much up in the air each day.
  • “When we not only automate and routinize the trivial parts of life, but also make automatic good and virtuous decisions, we free up resources to do important and meaningful exploration. We buy room for peace and stillness, and thus make good work and good thoughts accessible and inevitable.”
  • “Done enough times, done with sincerity and feeling, routine becomes ritual. The regularity of it – the daily cadence – creates deep and meaningful experience.”

Bits and Pieces

  • Limit your inputs. “If you wish to improve, be content to appear clueless or stupid in extraneous matters.” -Epictetus
    • This probably means not watching the news and being very careful which inputs make it into your body.
    • It also means preserving your pre-work and pre-phone brain – when you have time to think before the pressures of your day get on top of you. That mental space – the clarity you have in the morning and before the day’s craziness – is precious.
    • “Before we can make deep changes in our lives, we have to look into our diet, our way of consuming. We have to live in such a way that we stop consuming the things that poison us and intoxicate us. Then we will have the strength to allow the best in us to arise, and we will no longer be victims of anger, of frustration.” Thich Nhat Hanh
  • Anger is an unstable fuel and unlikely to yield long-term, sustainable success. Think about the athlete driven by rage to prove the haters and doubters wrong. How long does that last? How unhappy does it make them even if they succeed?
    • “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.”
    • Hilariously, Richard Nixon, a noted paranoiac and bigot, had a wonderful quote about this. “Always remember, others may hate you, but those who hate you don’t win unless you hate them. And then you destroy yourself.”
  • “Work is what horses die of. Everybody should know that.” There’s a word for death from overwork in Japanese (karoshi) and Korean (gwarosa). That’s a bit scary.
    • “Is that what you want to be? A workhorse that draws its load until it collapses and dies, still shod and in the harness? Is that what you were put on this planet for?”
    • That’s not to say you should never work or that you should become lazy and indifferent. But pacing your work is essential. Work (and life) are more a marathon than a sprint, and knowing when to stop is the key difference between those who burn out quickly vs. those who have long and sustainable careers.
    • Remember the story of John Henry vs. the steam engine. Henry wins, but dies of exhaustion in doing so. “In real life, it is always the anvil that breaks the hammer.” -George Orwell
    • “Work will not set you free. It will kill you if you’re not careful.”
  • Get some sleep. Lack of sleep can cause all kinds of problems – an increase in negative thinking, loss of creativity, and impairment similar to drunkenness.
    • “People say, “I’ll sleep when I’m dead,” as they hasten that very death, both literally and figuratively. They trade their health for a few more working hours. They trade the long-term viability of their business or their career before the urgency of some temporal crisis.”
    • “Sleep is the interest we have to pay on the capital which is called in at death. The higher the interest rate and the more regularly it is paid, the further the date of redemption is postponed.” -Arthur Schopenhauer
  • Quash envy with three questions: 
    • What if the rival you’re jealous of were to be jealous of you?
    • What if you had to trade places with the person of whom you’re jealous? Not just the thing you want, but their whole life for your entire life. Would you still take the deal?
    • What will happen to me if I get what I want? How will I feel after?

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