Keep Buggering On – or – The Obstacle is the Way

I predict Ryan Holiday will break the world record for writing the most quotable texts.

His The Obstacle Is The Way is book about  stoicism. And has a lot in common with buddhism (just finished Buddhism for Dummies).

Marcus Aurelius is Holiday’s big example, and the name-giver for the book and the core idea of the book.

“And from what we know, he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.”

And he himself quotes non-obvious but remarkable people.

He quotes Henry Rollins. Yes, Henry Rollins from Black Flag – the last person I had expected in this book.

I searched and found where this quote came from. Here is the Henry Rollins quote on being. Or rather his definition being a hero.

“People are getting a little desperate. People might not show their best elements to you. You must never lower yourself to being   person you don’t like. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.”

Holiday quotes Montaigne.

I did not know that Montaigne had a near death experience that became a turning point in his life. I found interesting but not very consistent stories on this here in the Guardian, here on NPR and here.

The book maintains a strong compelling tone.

I made a shitload of notes, as Tim Ferriss would say. All of them make you think. Some make me feel like a lame and lazy sod.

“We’re dissatisfied with our jobs, our relationships, our place in the world. We’re trying to get somewhere, but something stands in the way. So we do nothing. “

I plead guilty.

Ryan Holiday is so inspired by Aurelius that he has divided this book in three parts directly from Aurelius summary of what is needed.

“It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.”

On perception.

The way a person handles his emotions and is aware of his emotions is a key in mastering all situations.

“Where one loses control of emotions, another can remain calm. Desperation, despair, fear, powerlessness – these reactions are functions of our perceptions. You must realize: Nothing makes us feel  this way; we choose to give in to such  feelings. Or, like Rockefeller, choose not to. And he provides clear guidance to how to go about keeping your nerves under control and stay calm.”

“To be objective, To control emotions and keep an even keel,  To choose to see the good in a situation, To steady our nerves, To ignore what disturbs or limits others, To place things in perspective, To revert to the present moment, To focus on what can be controlled. This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process — one that results from self-discipline and logic. “

And he warns us that when we aim high, unpleasant things will haunt us, and this is where self control is your only way to stay up.

“When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almost guaranteed. The risk of being overwhelmed is always there. In these situations, talent is not the most sought-after characteristic.”

According to Holiday, The First Duke of Marlborough attributed his success to:

“tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.”

But who is this guy John Churchill? His name is really John Churchill, son of Sir Winston Churchill, sic! But this Winston lived from 1620–1688. And yes, our 20th century Winston Churchill is a descendant.

I love these details.

“Remaining calm is one of the most important skills to be learned to manage fear. And it can be trained.”

“Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve.”

“The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions.”

“Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?”

Now clearly that all sounds great in theory, but there are tools that help you achieve this coolness.

“Perspective is everything. That is, when you can break apart something, or look at it from some new angle, it loses its power over you.”

“So what if you focused on what you can change? That’s where you can make a difference.”

Ryan Holiday quotes Laura Ingalls Wilder.


Another fascinating detail, to me. I found she is a 19th century writer. Most known by the Little House series of books on which the television series The Little House on the Prairie was based. She had really lived a LittleHouseOnThePrairie life, as a settler in Kansas.

But here is why Ryan Holiday quotes her:

“As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.””

Or some unattributed quote:

““That which doesn’t kill me makes me stronger” is not a cliché but fact.”

On Action

Waiting for things to happen will not move things in the direction you want. Making things happen is.

“If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.”

“And again, it is in the act and persistence , not so much in the talent you have.”

He elaborates on this point that talent is often overrated.

“Too many people think that great victories like Grant’s and Edison’s came from a flash of insight. That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile. Their genius was unity of purpose, deafness to doubt, and the desire to stay at it.”

And the destiny is not the goal, it is the process to that goal, and you should focus on the process if you want to move forward.

“Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize. “

“The process is about doing the right things, right now.”

And get your boots dirty:

“Only self-absorbed assholes think they are too good for whatever their current station requires.”


“Think progress, not perfection. Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist.”

On will

If your have the right mindset, you are taking actions. Now it is the time to get going.

“To be great at something takes practice. Obstacles and adversity are no different.”

Anticipate hardships.

“Always prepared for disruption, always working that disruption into our plans. Fitted, as they say, for defeat or victory. And let’s be honest, a pleasant surprise is a lot better than an unpleasant one.”

About persistence and perseverance.

“Persistence. Everything directed at one problem, until it breaks.”

“Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.”


“Determination, if you think about it, is invincible  Nothing other than death can prevent us from following Churchill’s old acronym: KBO. Keep Buggering On.”

And that finally comes from the Churchill we know, Sir Winston …

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