Saturday, June 13, 2020

The Obstacle is the Way by Ryan Holiday

The Obstacle is the Way by Ryan Holiday is a solid book about stoicism and the writing of Marcus Aurelius (A.D. 121-180), Seneca, and others.

Holiday in the introduction notes that the book isn't a study of stoicism and the people who wrote about it, rather an attempt to "collect, understand, and publish their lessons and tricks." The hope is to show how to turn an obstacle into an advantage; overcoming obstacles is about perception (our attitude towards obstacles or problems), action (what we do about obstacles), and will (how we handle defeat or difficulty). There's good content from Holiday, with below each chapter in his book and what stood out from it:


The discipline of perspective - The goal is to see opportunity in difficulties. They're going to arise, so what becomes important is how we react.

Recognize your power - We can't always control what happens to us, but we can control how it affects our psyche and how it makes us feel. We're never completely powerless.

Steady your nerves - In situations that can overwhelm, grace, poise, and nerve are the most important characteristics someone can have as without them, other characteristics like talent can't be employed.

Control your emotions - Uncertainty and fear are relieved by training and logic. Through this, one can become in control of their emotions and not get rattled at the moments of greatest stress.

Practice objectivity - It's often better to observe obstacles, not also perceive them and  read into problems. Try to remove yourself from the equation in a situation, see it for what it is, not how you're impacted.

Alter your perspective - Look at problems from a new angle. Also, don't overstate the importance of problems, quoted is Richard Branson with "business opportunities are like buses; there's always another coming around."

Is it up to you? - Someone facing obstacles should be thinking of whether there's a chance at success. If there is, it may well be worth going after. Also, it's about focusing on things that can be changed, not what can't.

Live in the present moment - It's not worth the energy to spend thinking about whether things are fair or you're at a disadvantage. Remember also that a given time isn't your entire life, just a moment in it.

Think differently - Since our perceptions influence what can be done, it's often going to be best to simply be optimistic that something can be accomplished.

Finding the opportunity - When we control our emotions in looking at a problem, it enables the possibility of looking at the opportunity inside the obstacle, even if it's just seeing it as something to learn from.

Prepare to act - The worst thing to happen with a problem is to lose your head, then you have to deal with both the problem and your reaction to it.


The discipline of action - When you're dealt a bad hand or suffer a misfortune, should run towards it, looking to take action and improve your lot. What's important is what you do after something bad happens.

Get moving - Take an opening and press forward, or get the bat off your shoulder and take a swing. if you've done something, great, do more. Stay moving, always. If you want momentum, get started so it can create.

Practice persistence - Keep trying, if something doesn't work, try something different. The answer to how to do something may be entirely unexpected. It's supposed to be hard. First attempts aren't expected to succeed.

Iterate - There's nothing wrong with failing, it's how we know what doesn't work. Stories of great success are often preceded by stories of epic failure as improvement can come from it.

Follow the process - Think about the task at hand. Excellence is just a matter of steps repeated. Things at first are hard, and then they're not. Things don't happen all at once and small steps are better than no steps.

Do your job, do it right - Along the way to success, we're all going to have some jobs we don't want to do, do it with pride anyways, everything we do matters. A job is only degrading if we give less to it than we're capable.

What's right is what works - We get things done, by just that, by getting them done. Don't get too caught up in what you or someone else thinks is the correct way to do things. Do the best you can with what you've got.

In praise of the flank attack - Unexpected approaches are often the best kind. Be creative, find workarounds, and tactics others might not have thought of.

Use obstacles against themselves - Sometimes restraint is the best action to take, have patience and let things settle. Passive resistance can in fact be incredibly active.

Channel your energy - Adversity can harden you. Or it can loosen you up and make you better if you let it. It's seeking the right balance of physical looseness and mental tightness.

Seize the offensive - Use negative events as triggers to get things done, push forward. Life favors the bold at time of decision points.

Prepare for none of it to work - Nothing can prevent us from trying. Problems are a chance for us to do our best. Be the type of person who gets things done.


The discipline of the will - Will is taking on a onerous task without giving in to hopelessness, to be in great difficulty and tell oneself "this too shall pass." Strength in terrible times is when strength most needed.

Build your inner citadel - Nobody is born with a steel backbone, we have to forge it. We're going to be more successful toughening ourselves up than making the world easier. To be great at something takes practice.

Anticipation (thinking negatively) - Think in advance of what things can go wrong, that way you're not surprised by them, and you may even be prepared to deal with them. Know that things will go wrong.

The art of acquiescence - Be willing to accept, and not resent, a difficulty or shortcoming. You don't have to like something, but you can't let it control you. Things will do what they do sometimes, and we react from there.

Love everything that happens: amor fati - When bad things happen, they happen. We then should continue forward with unfailing cheer. We make the best of things.

Perseverance - It's not about what happens in the beginning, or the middle, it's continuing forward all the way through, to endure.

Something bigger than yourself - There's a bigger cause to life. It's not all about us. Whatever problem we're going through isn't really unfair, it just is what it is. Try to leave things a little better than before we started.

Meditate on your mortality - The things we think are so important, really aren't. If something is in our control, it's worth our energy. If something is out of our control, it's not worth our energy. Eventually we'll be gone.

Prepare to start again - Behind mountains are more mountains. There's always another challenge. Get used to it. Passing one obstacle means you're worthy of more.

The book has excellent wisdom to impart and in the preface, Holiday quotes what Aurelius wrote to himself...

"Our actions may be impeded... but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting. The impediment to action advances action. What stands in the way becomes the way."