What's Missing In The Obstacle Is the Way?

A review of the bestselling Stoic book

Welcome to The Stoa Letter, the newsletter on Stoic theory and practice.

Every week we share two emails to help you build resilience and virtue with ancient philosophy. Each email includes one meditation on Stoic theory, one action to do in order to become more Stoic, and links to the best resources we’ve found.

🏛️ Theory

Ryan Holiday’s The Obstacle Is the Way is one of the most widely read modern books on Stoicism. It is an inspiring book that serves as a fine introduction, but it’s a mistake to think that it captures the whole philosophy.

The book is tightly written and, for people who like its style, undeniably motivating. It grounds philosophy in action and real people. Stoicism is a life philosophy for doers – not a purely academic enterprise. I listened to it while running the other day and can attest to the book’s energetic force.

The main concern is that it doesn’t focus enough on the key reason why obstacles should be overcome. Nietzsche once said “a man who has any why can bear any how” – this book doesn’t offer a clear why. For the Stoics, our telos, or purpose, is to be excellent people and “live according to nature.”

Stoicism is a radical philosophy. The Stoics held that that virtue is the only good and vice the only evil. Everything else is indifferent. This is why any adversity can be overcome: we cannot be harmed.

The idea of character hovers in the background in The Obstacle Is the Way, but it can be missed.

This can sound like boring moralizing, but there is an essential philosophical point here. Adversity must be defeated for a sustainable and legitimate reason. When our life is driven by the pursuit of indifferents – wealth, pleasure, or status – it is not going well. Such things do not provide motivation worth having. Without determining the direction of one’s adventure, you may as well go anywhere:

When a man does not know what harbor he is making for, no wind is right.

Seneca, Moral Letters 71

This isn’t to say that the book hasn’t had a positive impact. It’s introduced many to Stoicism and continues to be widely read.

Perhaps the lesson of its popularity is that it’s better to introduce a single aspect of philosophy instead of the whole system. The risk of this strategy is that some may come away with a shallow picture of Stoicism. Without grasping the whole, one may not grasp anything.

🎯 Action

Bring to mind how you will embody excellent character today. Don’t let obstacles prevent you from making excellent judgments and choices.

🔗 Links

📚️ Ryan Holiday followed up The Obstacle Is the Way with many more books including Lives of the Ancient Stoics, The Daily Stoic, and his current series on the virtues. The Obstacle Is the Way does not exhaust his Stoic knowledge. In fact, you can read his output as an autobiographical journey. While young, unmarried, and hungry he writes The Obstacle Is the Way. As he grows in his studies and experience he turns his attention to the virtues.

My favorite book of his is Lives of the Ancient Stoics. It chronicles the lives of Stoics, both popular and unknown, such as Porcia Cato and Aristo of Chios. From each life, Ryan and his co-author, Stephen Hanselman, abstract simple and effective lessons.

🎧️ If you’d like to hear more of our thoughts on The Obstacle Is the Way, listen to our Stoa Conversation here. Michael Tremblay and I discuss what we like about the book, what we don’t, and what we find provocative. We go deep into Holiday’s use of the three disciplines of Stoicism.

📺️ We made a goofy AI video! That is, we made a short clip of the ancient Stoics depicted as fashion icons. It’s based off of this meme.

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