The Obstacle is the Way by Ryan Holiday

The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage by Ryan Holiday


The book is meant as an introduction to Stoicism and to an idea that stoicism in the West has been around throughout history behind the scenes as a tool for those who wanted to use it. The book comes formatted thus with some collected anecdotes about famous and successful people down the ages who have employed stoicism either consciously or unselfconsciously.

Some Observations

The anecdotes could have been a little longer or more detailed for me. As it was they come off a little like a laundry list, famous person overcomes obstacle’ then succeeds. The stories all too often fall down from lack of detail, context etc so they ended up feeling perfunctory. A good example was the story about Robin Hurricane Carter who went to prison unjustly and didn’t eat prison food’ how the hell did he do that and stay alive then?

The other problem is that the advice is repetitive, never nuanced and a little shallow;

But… No. No excuses. No exceptions. No way around it: It’s on you.’

That’s it, Really? I got a sinking feeling reading this book that its a kind of Stoicism’ for VCs in the Valley (see second quote below from my book notes) who think having lunch together is working. Just work harder’ or perhaps your employees harder and you will succeed, hey just check out Mark Zuckerberg’s new haircut, it must be true!


There are many good quotes in this book and it does make me want to delve into the Philosophy of Stoicism more you might get something out of it as a taster for some more stoic reading so in that sense the book works fine. But I felt that we never got above grazing the surface of a fascinating and enduring philosophy.

Book Highlights

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. And then he concluded with powerful words destined for maxim. The impediment to action advances action. What stands in the way becomes the way.

One can trace the thread from those days in the decline and fall of the Roman Empire to the creative outpouring of the Renaissance to the breakthroughs of the Enlightenment. It’s seen starkly in the pioneer spirit of the American West, the perseverance of the Union cause during the Civil War, and in the bustle of the Industrial Revolution. It appeared again in the bravery of the leaders of the civil rights movement and stood tall in the prison camps of Vietnam. And today it surges in the DNA of the entrepreneurs of Silicon Valley.

Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That’s all you need.

Marcus Aurelius

We can see disaster rationally. Or rather, like Rockefeller, we can see opportunity in every disaster, and transform that negative situation into an education, a skill set, or a fortune.

Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.


Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

Would you have a great empire? Rule over yourself.


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. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind. Don’t let the negativity in, don’t let those emotions even get started. Just say: No, thank you. I can’t afford to panic.

Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness? Nope. Then get back to work!

In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices.


A good person dyes events with his own color… and turns whatever happens to his own benefit.


But… No. No excuses. No exceptions. No way around it: It’s on you.

We must all either wear out or rust out, every one of us. My choice is to wear out.


What is defeat? Nothing but education; nothing but the first steps to something better.


Whatever is rightly done, however humble, is noble. (Quidvis recte factum quamvis humile praeclarum.)


The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know.


In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases.


See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.

January 6, 2020