Book Notes: The Obstacle is the Way

The Obstacle is the Way, by Ryan Holiday, helps put obstacles in perspective and explains how one can navigate hurdles as they come your way. It references a lot of Stoic philosophy, while also giving real-world examples and practical advice.

Often, when faced with obstacles, one’s instinct is to avoid them. This book argues that the obstacle is there to teach you something, and is a signal to lean into the thing blocking your path to learn.

Obstacles Are There to Teach Us Things

• Similar to principles described in The Dip, by Seth Godin and The Subtle Art of Not Giving a Fck, by Mark Manson, obstacles are there to teach us things. If we avoid them, we avoid valuable lessons. Instead, look to navigate through obstacles and learn valuable things along the way.
• An obstacle is an invitation for us to act. Don’t overthink, don’t over-prepare, or over-analyze. Just start working at it. The quicker you start working at something, the faster you start learning and know what approaches you need to tweak to be most effective.
• Obstacles can serve as fuel for ambition. Use them to propel you forward. If you see an obstacle in your way, know it is there to teach you something. Run to it, be comfortable being uncomfortable, and lean into that discomfort to learn something new.
• As I’ve described in Get Those Reps In, those who have mastered something know the exact forces to exert and the exact energy required to accomplish something. You become more efficient at something over time and exert less energy. You’ll know the critical moves necessary to get something done.
• Furthermore, you’ll start to appreciate the benefits of mastery after you’ve reached Critical Mass. Adopting the right practices and habits can help you get there.
  

Master Your Emotions When Facing Obstacles

• Obstacles tend to make us fearful, angry, frustrated, helpless, or confused. By being mindful of this, you’ll be better equipped to manage those emotions as they happen.
• Don’t suppress these negative emotions when an obstacle surfaces. Instead, if you embrace and manage them, you’ll learn to master these feelings. This mastery will make it easier to navigate the obstacles themselves.
• It is important to remain calm in the face of obstacles. Mastery over negative emotions that come with obstacles will help you remain calm and poised to make better decisions to overcome whatever stands in your way.
• Calmness in the face of adversity is a competitive edge against those who either look to use it against you or are reacting emotionally themselves.
• Use sub-optimal situations to your advantage. They’ll give you opportunities to do things that you normally wouldn’t do and bring you outside your comfort zone.
  

Overcoming Obstacles

• Opportunities are abundant. It’s not about executing an idea, it’s about executing the right idea.
• When facing an obstacle, be willing to experiment, observe the results, then tweak your approach. Think of it as the scientific method. Remove emotion from your approach, and instead, hypothesize, experiment, observe, then repeat.
• Stay persistent on your vision, but be very flexible in your approach to get there. The more agile you are in your tactics, but the firmer you are in your vision, the more likely you are to hit your goal.
• There is always a new, creative way to do something, and you aren’t required to meet an obstacle head-on with the same force the obstacle is exerting on you.
• Anything worth doing will have an obstacle.
• It’s not cheating to find shortcuts around obstacles. It’s part of the learning process to discover those shortcuts. It’s strategy. It’s creativity.
• Choosing not to act can be an action, as long as it is done purposefully, mindfully, and not for avoidance. Not acting can buy you time to gather more information and make a more informed decision.
• Be strategic in how you tackle obstacles and how much energy you spend on each. Life is a marathon, not a sprint. If you expend all of your energy on each obstacle, you’ll never retain enough energy to make it anywhere.