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The Obstacle is the Way

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Reads like a "devotional" book without religious overtones. I enjoyed it and it made a positive impact on me. Will likely read the other related books.


I grew up Evangelical Christian so “Stoic Philosophy” wasn’t in my vocabulary. Daily "Devotional" books however were common. “The Obstacle is the Way” is a devotional book without religion. That isn’t to demean or devalue the book, I enjoyed it for the most part. But that this book follows the same structure: a quote to begin, a few pages on a topic, and leaves you with a virtue to pursue. The structure is comfortable and not overwhelming. It is meant to convince or maybe encourage the reader to pursue the same virtues the Stoics held in high esteem.

For the most part I was convinced. I want to be more even keeled, thoughtful, resourceful, and see problems with clarity that solutions always lie on the other side. It’s hard in roughly 4 pages per chapter to cover all the nuances of the topic and my brain naturally looks for exceptions to disprove rules, but Holiday successfully uses venerated people as proof for the qualities a Stoic possesses.


My main takeaways are:

  1. “Conquer problems from a different angle”
  2. Use your mortality to motivate rather than debilitate.
  3. Be calm in adversity.

One quick example of how I've used the final takeaway with my kids. I have a five-year old who was recently going through a rough patch with her behavior. My natural tendency is to engage the situation and cut out the issue. Sometimes this leads to a quick escalation of a non-issue. Most often I end up feeling guilt with how I responded later. But recently I've started to take a different tact. I get on her level and as calmly as I can, ask questions to see what's actually wrong. I reassure her and make sure my child knows I can handle their "big feelings". I empathize with her about why she doesn't want to go to bed. It's made a big help. Simply by changing my demeanor.

Final Words

I won’t say the book is a "must read." But I will admit that I am convinced enough to pursue more Stoic philosophy. I’m looking forward to reading some biographies and collections of philosophies from those people Ryan Holliday admires. I'll probably catch his next book in the series at some point.

Rating / Links

⭐️⭐️⭐️ out of five.
Buy the Obstacle is the Way