The Obstacle is the Way by Ryan Holiday is all about how to approach any challenge in your life with a level head and how to turn each obstacle into an advantage.
Pairs With: a Kinder Bueno! The first time I tried one of these I was walking on a frozen lake in Minneapolis when it was 7℉ out. The obstacle was to finish the 2-mile loop and not go back to the warm car.
Overview
The Obstacle is the Way by Ryan Holiday is all about approaching challenges in your life with a sensible mindset and making obstacles work for you. As Holiday states, “This is not a book of gushing, hazy optimism… I want to show you the way to turn every obstacle into an advantage.” Holiday does that by breaking the book into 3 sections: Perception, Action, and Will.
This book is a quick read thanks to the easy-to-digest, nicely sized chapters (not too long or too short) and interesting historical short stories. Similar to Holiday’s other works, the lessons within each short story typically correlate to lessons from Stoic philosophy.
Part I Perception
Part I is Perception where Holiday explains how to view problems sensibly. This section is all about how important it is to keep your emotions in check and to change your perspective when looking at an obstacle. Is there something here that will benefit me? Or do I need to reframe this so it just bothers me less?
Holiday quotes Marcus Aurelius, “Choose not to be harmed – and you won’t feel harmed. Don’t feel harmed – and you haven’t been.”
Part II Action
Part II is about Action and what action to take when addressing obstacles. Holiday recommends not getting thrown off course or flustered by a challenge. Instead, he explains the importance of sticking to the process. When we panic, we ignore the procedures we had in place to succeed and we end up making the obstacle harder on ourselves. Often making unnecessary mistakes. Rather, stay the course, keep your head down and continue doing your job.
Part III Will
Part III is about Will and the internal power of our heart and soul. It’s about how you respond when the action doesn’t work and the situation is unchangeable. This section is about taking a step back and understanding no matter how ‘right’ we approach something, sometimes it is not within our control. (Or as my father so poetically likes to say, this is part where you “throw your hands up and say fuck it.”) This is when you realize you’ve tried your best and the outcome is going to be what it will be.
Conclusion
The Obstacle is the Way is a great book for anyone looking to change their approach to any obstacle they may be facing in their life. Some of the info in this book may be things you’ve heard before however, through historical examples, Holiday provides various reminders on how to turn an obstacle into an advantage.
Have you read this one or any of Holiday’s other works?
P.S. If you liked this one you may also like Holiday’s book Ego is the Enemy or Stillness is the Key.
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