Book Notes: The Obstacle is the Way, by Ryan Holiday
APRIL 23, 2016
Below are the notes I took while listening to the audiobook, The Obstacle is the Way, written and narrated by Ryan Holiday. Many of these notes were initially written from my phone, sometimes while running. So, please excuse the brevity and any typos I overlooked. The book is an excellent introduction to stoicism and has valuable lessons for anyone. In particular, I have and will continue to put this at the top of recommended reading for entrepreneurs. The notes in no way do justice to the book. They are intended to serve as a supplement to your reading or serve as a refresher if you've already read it. If this is of value, please feel free to check out other book notes with the tag below. Thank you!
Obstacles are an opportunity to practice some virtue.
Turning obstacles into opportunities is the commonality of successful warriors, businessmen, entrepreneurs, and people.
Andy Grove: "Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them."
This book is about pragmatism. To show you how to get unstuck, unfucked, and unleashed. How to turn negative into positive.
This is not about turning things into, "This isn't so bad." But instead, how can I make this good?
Steal good fortune from misfortune.
All great victories - political, business, art, or seduction - involved solving vexing problems with a potent cocktail of creativity, focus, and daring.
Overcoming obstacles is a discipline of 3 critical steps:
Begins with how we look at our specific problem, our attitude or approach
Then the energy with which we actively break them down and turn them into opportunities
Cultivation of an inner will that allows us to handle defeat and difficulty
Obstacles should be not just accepted but embraced.
Limit passions and the control they have over our lives.
Self-discipline guided Rockefeller; the greater the chaos the calmer he became.
Warren Buffett: Be fearful when others are greedy; be greedy when others are fearful.
What matters is not what obstacles are, but how we see them, how we react to them, and whether we keep our composure.
Reacting emotionally can turn bad things into really bad things.
Seen properly, every catastrophe is an opportunity to move forward.
Choose not to be harmed, and you won’t feel harmed. Don’t feel harmed, and you haven’t been.
We are never completely powerless.
There is nothing good or bad; our thinking makes it so.
Steady your nerves: "What such a man needs is not courage, but steady nerve control and cool headedness. This, he can only get from practice." - Teddy Roosevelt
When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard… the risk of being overwhelmed is always there.
If your nerve holds: Nothing really did happen.
In the space race, astronauts were trained especially in handling crises and not panicking.
When you worry or react emotionally, you are not solving problems and you are not thinking constructively; you are misallocating energy.
If an emotion can’t change the condition or situation you are dealing with, it is likely an unhelpful emotion.
Real strength lies in control of one’s emotions, not in pretending they don’t exist. Feel it, just don’t lie to yourself by conflating bemoaning a problem with dealing with it. They are not the same thing.
You are not going to die from the problems you are encountering.
The phrase, "This happened and it is bad" is really two observations.
Think-perceive-act in milliseconds can be influenced, but it takes training.
Be objective: Think about how easy it is to solve other people's problems.
You decide whether or not to put an "I" in front of something (e.g., I screwed up) and to become obsessed about a small issue.
Richard Branson: "Business opportunities are like busses, they come around quite often."
Separate issues into things you can control and things you can’t. If you can’t control it, there is no use investing emotional energy towards it. If you can control it, even if only in a minor way, invest your energies towards that. Focusing on the former is self-indulgent and self-destructive.
Live in the moment, which is harder than it sounds. It's not enough to just say, "I'm going to live in the moment." It takes work. Remember that this moment is not your life, it is just a moment in your life
There is good in everything if you only look. Everything.
In life, it doesn't matter what happens or where you came from. What matters is what you DO with what you were given.
Action overcomes obstacles. Not words or thoughts. Articulating a problem is not the same thing as solving it.
Don't feel sorry for yourself. Get moving. And always be moving. Always.
It's ok to be discouraged. It's not ok to quit. Persist and resist. Stop looking for angels; start looking for angles.
Use the MVP startup model of "fail and iterate" on yourself. See yourself as a startup. Breakdowns happen when people interpret failure the wrong way. Great success is often preceded by great failure.
Failure shows us the way by showing us what isn't the way.
Being trapped is a position, not a fate.
You are so busy focusing on the future that you don't take any pride in task that you're given now.
Only a self-absorbed asshole thinks he's better than his current station in life (better than this job, etc.).
Do the job in front of you and do it well.
Solve the problem in front of you. Monumental breakthroughs were works in progress.
Only 6 in 286 battles studied were fought head on.
Head-on is the most difficult approach oftentimes.
Restraint may be the best action you can take. Sometimes the problem needs less of you.
Action isn't just moving forward. It can be standing still or even backward. Progress comes in many directions.
Mentally tight, physically loose
It is not enough to capitalize on opportunities that present themselves. You have to create opportunities and turn crises into opportunities.
The crisis is not just turned upside down but used as a catapult.
"Cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune's habit of behaving just as she pleases." - Seneca
Infinitely elastic formula: that which blocks our path always presents a new path with a new part of us.
The will is the third discipline. Will is not how bad we want something. True will is quiet humility, resilience, and flexibility. The other will is weakness disguised by blustering ambition.
Prepare for the hard road. Nobody is born with a steel backbone. We have to craft it ourselves.
You chose this for yourself, a life of doing things. Now you need to be prepared for what that entails.
The only thing assured is that things will go wrong. And the only thing we can do is anticipate bad things happening... Think, "What if..."
Unexpected failure is most discouraging.
Constraints on us are a good thing.
If we took traffic signals personally, we'd go insane. We accept detours and closures but don't let them prevent us from reaching our destination. Apply the same principles to other obstacles.
Perseverance and persistence are different. The former is the long game. The latter is an action and the former is a matter of will. One is energy the other endurance.
Meditate on your mortality. Life is a gift.
There is no such thing as overcoming an obstacle and not having any more obstacles. It's the opposite. The more you do, the more obstacles stand in your way. Passing one obstacle just proves you are ready for more.
"A stoic transforms fear into prudence, pain into transformation, mistakes into initiation, and desire into undertaking." - Taleb Nassim Taleb
We gather strength as we go.
The essence of philosophy is action.
Afterword, with Tim Ferriss:
The problem isn't having wealth. It's when wealth has you.
Asking people for favors has, based on studies, shown that they become indebted to you.
Best books: How to Live; The Fish that Ate the Whale; Titan; Edison: A biography.
Read: "Maker's Schedule, Manager's Schedule," essay by Paul Graham.
Email may be faster but it's usually less distracting.
The best writers live interesting lives.
Pick up a copy of The Obstacle is the Way here: