Coffee House Reading #17:
The Obstacle Is The Way

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

-Marcus Aurelius, former Emperor of Rome

The Obstacle Is The Way by Ryan Holiday is a book I regret not having read the first time I heard about it. It’s an overview of stoic philosophy combined with stories of how people triumphed over adversity throughout history. There are a great number of books that follow this pattern of explaining ideas through short, seemingly anecdotal stories (see How to win friends and influence people). At times, the stories in these books are entertaining. At other times they seem distracting, as though they take away from the message of the book. Holiday’s book, however, is one of the few in which the main concept is constantly strengthened by its tales.

To show what I mean, take the basic concept: the obstacle is the way. Holiday took the phrase from Marcus Aurelius, one of the greatest stoic philosophers of all time and author of Meditations. Think about it, apply it to anything you have gone through, and guess what it might entail in any future situation. Ask yourself how an obstacle could be the way. Evaluate how much depth this idea has in your situation. Now, let’s see a few examples of people who have embodied this philosophy.

The following examples are taken from the three main sections of the book: perception, action, and will.


One person sees a crisis, another can see opportunity.

Our perception guides our actions and inactions. However, it can oftentimes fool us, giving us confidence when we should not have it, or keeping us small when we need to act. To be in command of one’s view of the world, to see reality for what it is, is one of the key concepts of stoicism.

John D. Rockefeller, one of the wealthiest Americans of all time, stands out in the book through his perception of struggles and crises. He describes the years of struggle he had as an apprentice as a blessing. Rockefeller did not only live throughout the American Civil War and several economic depressions, including the Great Depression of 1939; he managed to also accumulate a great deal of wealth and resources.

He achieved all of this precisely by seeing things for what they are, and not for what they appear to be. He once turned down the opportunity of investing half a million dollars in oil fields because it did not feel right. The money was offered to him by investors at the young age of 25, yet he did not give in to temptation, to any superficial desires of getting rich quickly. Decades later, he would control 90% of the oil market. What others saw as opportunities, he was able to dismiss as imprudent ventures, and where others saw danger, he prevailed with decisive action.


They start. Anywhere. Anyhow.

Amelia Earhart was the first female aviator to fly solo across the Atlantic. However, when she was first given the opportunity, the offer was that she would be paid nothing, would not be able to directly fly the plane, and would be accompanied by two men. Women could not be pilots at the time, so she was making her actual living as a social worker.

Her response to the apparently ludicrous offer? She accepted, knowing that once started, she could get momentum, she could find new opportunities to achieve her dream. She did not wait for a perfect opportunity, ignoring every chance she might get simply because they might fall under the guise of not good enough. 5 years later she achieved her dream of doing it solo.

Earhart had the following words written on her plane: “Always think with your stick forward“.  The stick she was referring to was the throttle of the plane, meaning that you cannot give up speed on your journey. You need deliberate and right action, but you cannot allow yourself the luxury of waiting for ideal circumstances. Always move forward.


Amor Fati.

The will is the final chapter of the book, describing that power inside ourselves to focus on what we can control and not on what is outside of our control. It is what we have left when all else fails, when a situation seems bleak. Even more so, it is what we can call upon in times of turmoil when we choose to laugh in the face of adversity.

Thomas Edison, the inventor of the lightbulb, once had his entire factory burn down to the ground. His response? With excitement, he told his son to bring his mother and her friends to see the spectacular blaze. He was cheerful and made the best out of a, truly, bad situation. For Edison, it was the only appropriate action. Nothing else he could do would change the circumstances. So he saw the good in the bad. Within months, he was able to rebuild everything.

And you?

So let’s get back to that phrase:

The obstacle is the way.

What is your obstacle and how real is it? Are you waiting, or are you moving forward? And how are you reacting to it? When challenged, remember some of these stories of people who’ve been in dire straits and think about how they overcame their circumstances. Your obstacle might also be your way of progressing, instead of stagnating.

These are three examples from a quite remarkable book. But they are only small parts of the whole, of a philosophy which requires a lot more nuance to understand. For now, you can supplement the book with a TED talk from Tim Ferris, bestselling author, podcaster, and serial investor. In it, he talks about how stoicism is his mental operating system and something which saved his life.

The best Viennese Coffee House to read this book in

The best place to read this book is Pickwick’s in Vienna. It’s a great café with good music and plenty of their own books on the shelves. More importantly, it’s on Marc-Aurel-Straße. Yes, that Marcus Aurelius. What better place to read a book on stoicism than on a street named after one of its creators?

Cover image by Namroud Gorguis on Unsplash.

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About Radu

Radu studied film & computing, works in EdTech as a content creator, and reads nonfiction books in his spare time.

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