The Obstacle Is the Way – Notes and Thoughts

By Ryan Holiday


This was an easy but worthwhile read. It didn’t have the usual complex writing like many of the classic stoic philosophical texts often do. Instead, The Obstacle Is the Way is an easily digestible book that merges many stoic principles into a modern context. This is a book that I know I’ll return to at various points in my life. The type of book that I will interpret differently after more life has passed. I like that type of book. It’s like a gift that keeps on giving.

It’s also why I like to take notes on what I read. I have so much fun rereading a book and seeing how the book impacted me at the time and how I interpret it at a later date. Seeing how my mentality has changed over time is fascinating.

My Notes & Thoughts

Mentality is important to success. How you approach problems, face defeat, adversity, and interact with others is more important now than ever. Life in the Information Age is a mixed bag of signals that impacts how we approach problems.

On the one hand, we have become accustomed to the instant gratification of the on-demand economy. Consumerism boosted by constant mobile internet access. On the other hand, we are faced with the reality that if you want to build anything of value, it takes time, patience and a mentality of perseverance. These mixed signals make it hard to determine what the appropriate path forward is.

The Obstacle Is the Way by Ryan Holiday is a great book on stoic mentality. An operating system for approaching the challenges of life. A way to think and approach timeless challenges.

The book is important because it addresses how we can approach individual and shared realities. Reality is how we perceive the facts of our lives. Shared realities are the community perceptions of these same facts. Holiday’s book provides actionable wisdom for how to interpret the facts of life to better exist in our communal reality.

Below are some of the highlights from my first read through.


We cannot control the facts of life but we can control how we interpret and allow them to influence our mindset. Although mindset is incredibly important, at the end of the day it won’t’ move an obstacle. Only through action can we change our individual circumstances.

Don’t be afraid to think and act differently. The community you live in may have judgements of your thoughts and actions but your ability to think differently makes you a value to the community.

Your individual reality is not the same as the judgements made by your community’s shared reality. You are an individual in a community, your truth is not always going to be the same as the community’s truth. You must face these facts of your life. Build a personal plan of action and execute for your personal benefit. Regardless of community judgement.

Your starting circumstances become irrelevant in a shared reality. What matters is your ability to take your situation, adapt to its circumstances and take action to improve your life.

Building positive momentum towards action is important to maintaining a strong mindset.

Persistence is an important attribute for generating momentum.

“Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.”

 “In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up—a start-up of one.”

This is an essential mindset for the Information Age. As our lives become increasingly digital, our future business prospects will become increasingly individualized. By viewing yourself as a unique startup, you are forced to take personal responsibility and accountability for building your own future. An end to the reliance on the standardized processes of the past and a shift towards personal resilience. An end to fatalistic mindsets.

When you work for yourself and are personally responsible for your own future, you must become accustomed to iteration and the failure that comes with it. The sovereign individual is a one person company and an MVP that must get comfortable with the iterative failure of creating

Personal responsibility for your future is a process. The iterative nature of failure and success along the way will take a lot of time and tinkering to fully develop into success. By breaking down a goal into tasks and focusing on what needs to be accomplished in the present, goals become more manageable.

As you work through your process to achieving your goals its important to be realistic. To be flexible. Not everything always goes according to plan. You will fail a lot along the way. By being flexible, you adapt to the circumstances as they are presented in the present, in order to take the best actions to achieve your goal.

Progress doesn’t have to be linear. It doesn’t have to be perfect. And it certainly doesn’t have to be sexy. Whatever path forward gets you to achieve your goals is the best path forward. Sometimes that means avoiding obstacles and sometimes that means attacking them head on. It’s important to do whatever works.

“You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.”

Take the opportunity that is presented to you, whether it’s ideal or a crisis. Opportunity is a mindset, like the saying – one man’s trash is another man’s treasure. 

Holiday calls this internal mindset the Inner Citadel, the ability to take any obstacle or adversity and convert it into an opportunity. Your Inner Citadel is like a structure, it must be built and actively maintained or it will wear down in time.

Although it’s important to cultivate a mindset that adversity can be overcome, it’s also important to face reality. You aren’t meant to be successful in all things. If you possess a weakness, it’s ok to acknowledge that weakness and build an alternative path forward. You must be real with yourself.

You also cannot expect everything to go right regardless of how much preparation you have done. Simple probabilities of outcome prove that you won’t always be perfect. That’s ok. You cannot be in control of all aspects of your life. Having expectations that all your plans will be perfectly executed sets you up for disappointment and harms the integrity of your Inner Citadel.

You cannot control everything but you can control your mindest. When things don’t go according to plan you can control how you react to the outcome. You can choose to happily move forward or you can wallow in defeat.

When building a resilient mindset remember that if it were easy everyone would be doing it.

Persistence is to short term problem solving as perseverance is to longer term problem solving.

“Emerson wrote in 1841, If our young men miscarry in their first enterprises, they lose all heart. If the young merchant fails, men say he is ruined. If the finest genius studies at one of our colleges, and is not installed in an office within one year afterwards in the cities or suburbs of Boston or New York, it seems to his friends and to himself that he is right in being disheartened, and in complaining the rest of his life.”

Achieving your goals takes as long as it takes. Don’t lose sight of the personal process your journey requires by comparing yourself to others.

When building a long-term mindset, it can sometimes be helpful to focus on helping others. I.e.: you are less likely to let your community down than you would yourself. It can sometimes be easier to fight on behalf of others than it can be to fight for ourselves.

There will always be obstacles. Once you overcome one challenge, there will absolutely be others down the road. Don’t expect otherwise. There is no point in being intimidated or frustrated with this reality. Instead, you control the mindset for which you approach all future challenges.

Learn to embrace the process. If you can conquer the mindset required for this process, the obstacles become the way.

Closing Thoughts

In general, this was a quick, easy and rewarding read. If anything, this book has peaked my interest in exploring some of the Stoic classics.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s