The Obstacle is the Way


With short but sweet advice and pointed historical examples, Ryan Holiday envelops you in a Stoic world where people not only can conquer any obstacle, but take advantage of it, enjoy it and become better and stronger people because of it. Holiday is a very interesting guy who has worked closely with critically acclaimed author Robert Greene since dropping out of college at age 19 and I would highly recommend his podcasts with Tim Ferriss.

The Rabbit Hole is written by Blas Moros. To support, sign up for the newsletter, become a patron, and/or join The Latticework. Original Design by Thilo Konzok.

Key Takeaways
  1. The most successful people have a method and a framework for understanding, appreciating, and acting upon obstacles life throws at us. Great individuals and great companies find a way to turn weakness into strengths. The greater the obstacle, the greater their/its strength becomes (pair with Taleb's amazing Antifragile)
  2. Every obstacle is unique to each of us but the responses they elicit are the same - fear, frustration, confusion, helplessness, depression, anger
  3. With the advice in this book you will be able to attack any obstacle by seeing clearly, acting correctly and enduring and accepting the world as it is
  4. Our perception can be a source of strength or our greatest weakness
  5. See things as they really are, without their legend or ornamentation
  6. Live in the present, day by day. Do not always try to figure out what things mean - why they are the way they are.
  7. Don't waste time on false constructs
  8. Of course you want to avoid negative situations if you can but what if you were able to remember in the moment the second act, that opportunity to improve even the slightest, that comes with unfortunate situations
  9. Action is commonplace. Proper action is not
  10. Genius often really is just persistence in disguise
  11. Stop looking for angels and start looking for angles
  12. What is defeat? Nothing but education; nothing but the first steps to something better
  13. We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work
  14. Will is our internal power which can never be affected by the outside world. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised as bluster and ambition
  15. Love everything that happens - Amor Fati
  16. Death gives life meaning. Having that finite timeline pushes you and inspires you
What I got out of it
  1. As we all know, simple often does not mean easy. The themes in this book not only cover how to face and conquer obstacles, but how to live a happy and successful life. Much of the advice may not be novel, in fact much of it is Stoic and dates back thousands of years, but it is nevertheless invaluable. People are capable of anything as long as they don't confuse perception with observation, can learn from their mistakes and can embrace the problems everybody undoubtedly will face with a clear mind, acting correctly and accepting the world as it is.
  • Marcus Aurelius believed in turning obstacles upside down. To act with a "reverse clause," so that there is always a way out or another route to get where you need to go. Setbacks or problems are always expected and never permanent. Make certain that what impedes us actually can empower us
  • Aim of the book is to turn every obstacle into an advantage
  • All great victories, be they in politics, business, art or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus and daring
  • "The things which hurt, instruct" - Benjamin Franklin
  • Great times are great softeners. Abundance can be its own obstacle
  • Overcoming obstacles has three critical steps:
    1. How we look at our specific problems, our attitude or approach
    2. The energy and creativity with which we actively break them down and turn them into opportunities
    3. The cultivation and maintenance of an inner will that allows us to handle defeat and difficulty (perception, action and the will)
Part 1 - Perception
  • Our perception can be a source of strength or our greatest weakness
  • We must eliminate overly emotional reactions and see things as they truly are - neither good nor bad
  • John D. Rockefeller
    • Always had sangfroid and noticed what others did wrong and learned from it and used it to his advantage
    • Only the rational and disciplined mind would be able to thrive in our unpredictable world
    • Could resist impulse in favor of cold, hard common sense
    • Nothing makes us feel this way (panicked, frightened); we choose to give in to such feelings (or choose not to)
  • Rubin "Hurricane" Carter
    • Convicted of a triple homicide he didn't commit and instead of giving up while in prison he embraced his only real freedoms - his attitude, his beliefs and his choices. He focused all of his energy and every waking moment to reading law and anything else that would help him get out. He left prison a better man
    • This can't harm me - I might not have wanted it to happen, but I decide how it will affect me. No one else has the right
    • Turn mistakes into training
  • Laura Ingalls Wilder
    • Author of the Series Little House and looked at every obstacle as an adventure and an opportunity
  • Ulysses S. Grant
    • Had nerves of steel - a man who steadied himself properly; a man who has a job to do and would bear anything to get it done
    • Nerve is a matter of defiance and control
    • Grace and poise above talent
    • Astronauts were trained to remove panic. They'd practice everything so no variable was new on the actual day of the launch. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity
    • Must be able to avoid falling trap to these emotions so you can spend your energy solving problems rather than reacting to them
  • Miyamoto Musashi
    • The perceiving eye is weak, the observing eye is strong
    • Our animal brains try to compress the time from perceiving to acting - we can question and disregard this
  • Pericles
    • Perspective is everything. Fear is debilitating, tiring and often irrational. By taking something apart or look at it from a new angle, it loses its power over you
    • Take what scares you, break it apart and understand it from a new angle
    • Use context and framing to help see situations in a different light
    • Right action follows the right perspective
  • Tommy John
    • A pitcher who played for 26 seasons and would not give up unless there was literally nothing else that was in his control that he could do
    • Stoic phrase - ta eph'hemin, ta ouk eph'hemin - What is up to us, what is not up to us. 
    • Clearly, and realistically, know and understand the difference between what is up to you and what is not up to you
    • Was about to get dropped by the Yankees but convinced them to give him a chance as if he was a rookie at spring training and if he deserved to be on the team, they would pick him up. Sure enough, he made the team beating out people more than 20 years younger than him
  • Unplug - meditation, exercise, walking, getting a dog...
  • Steve Jobs
    • Learned early on that what people perceived to be impossible was often way off and pushed people harder than pretty much anyone in order for them to see the true possibilities
    • Although our doubts and self-doubts feel real, they have very little bearing on what is and isn't possible
    • Jobs didn't tolerate people who didn't believe in their own abilities to succeed. Even if his demands were unfair, uncomfortable or ambitious
  • Proper observation and not flawed perception allows for a clear head but then that clear head must act
Part II - Action
  • Action is commonplace. Proper action is not
  • Action requires courage, not brashness - creative application and not brute force
  • Right action is the solution and the cure to our predicaments
  • Demosthenes
    • Perhaps the best orator of all time who had to overcome a speech impediment and sickness but devised his own strange exercises to help him power his voice
    • He shaved half his head so he'd be too embarrassed to go outside and focus solely on his exercises and reading
    • He was strong and successful precisely because of what he'd gone through and how he reacted to it
    • It feels better to ignore or pretend but you have to act
  • Amelia Earhart
    • First woman to fly transatlantic in a time where women were thought of as too frail to do most things. But that's what people who become great do - they start. anywhere. Anyhow. They don't care if the conditions are perfect or if they're being slighted
  • When you're messing around, traveling, sleeping, etc. you're going soft. You're not aggressive enough. You're not pressing ahead.
  • Stay moving, always
  • Just because the conditions aren't exactly to your liking, or you don't feel ready yet, doesn't mean you get a pass. If you want momentum, you'll have to create it yourself, right now, by getting up and getting started.
  • Thomas Edison - persistence is the absolute key. Edison did not once fail, he found 10,000 ways not to make a light bulb
  • Never in a hurry; never worried; never desperate; never stopping short
  • In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start up - where we can learn and improve with every bit of feedback (millions of iterations)
  • Great entrepreneurs are never wedded to a position; never afraid to lose a little of their investment; never bitter or embarrassed; never out of the game for long
  • Lessons come hard only if you're deaf to them
  • Failure shows us the way by showing us what is not the way
  • Nick Saban
    • The Process - Don't think about the future whatsoever. Focus on the smallest task at hand. And do it the best. The rest will follow
    • Excelling is a matter of steps. Do not get distracted by anything that is not the task at hand. When it comes to our actions, disorder and distraction are death
    • The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture
  • Whatever is rightly done, however humble, is noble. - Sir Henry Royce
  • Everything we do matters. Take pride in everything you do and always do your best
  • In every situation, life is asking us a question and our actions are the answer. Our job is simply to answer well
  • How you do anything is how you can do everything
  • What's right is what works - do whatever you have to do to figure out your issue
  • Pragmatism is not so much realism as flexibility
  • Only 2% of campaigns were as a result of a direct attack on the enemy's main army. If not from pitched battles, where do we find victory? From everywhere else. From the unexpected
  • What separates many masters is that they choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics
  • Use obstacles against themselves - sometimes you overcome obstacles not by attacking them but by letting them attack you. You can use the actions of others against themselves instead of acting yourself
  • Nonaction can often be action. Find a means of making obstacles defeat themselves
  • Every negative, when examined and probed long and hard enough, can be turned into a positive
  • You must press forward precisely when everyone around you sees disaster
  • You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term are now immediate and must be dealt with. A crisis provides the opportunity for us to do things that you could not do before - Rahm Emanuel
  • Take advantage of every crisis - Obama did an amazing job of this during the race scandal with Reverend Jeremiah Wright and delivered what became known as the "A More Perfect Union" speech
Part III - Will
  • Will is our internal power which can never be affected by the outside world. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised as bluster and ambition
  • Abraham Lincoln
    • Had an incredible will and was able to resign himself to an onerous task without giving in to hopelessness, he was able to rise above the din and see politics philosophically
  • The will is the discipline of the heart and soul and is the one thing we control completely, always
  • It's much easier to control our perceptions and emotions than it is to give up our desire to control other people and events
  • Build your inner citadel - Theodore Roosevelt literally worked the weakness and asthma out of his body. Make sure you are ready emotionally, psychologically and spiritually for tough times no matter what they hold
  • Use premortems to your advantage - anticipation (thinking negatively) before an event happens in order to bring up any concerns before its too late (pair with Seneca's Letters from a Stoic).
  • Nothing happens to a wise man against his expectations...nor do all things turn out for him as he wished or as he reckoned - and above all he reckoned that something could block his plans - Seneca
  • It is important to be realistic - to be aware and accept, rather than resent, the fact that we have certain strengths and certain weaknesses. Develop your weaknesses instead of resenting and ignoring them
    • Accepting is far different, and far tougher than giving up
    • It's time to be humble and flexible enough to acknowledge that we are not in control of most things and accept and embrace that
  • Love everything that happens - Amor Fati
    • Don't waste a second looking back at your expectations. Face forward, and face it with a smug little grin
  • Persistence - everything directed at one's problem until it breaks
    • There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events
    • The good thing about true perseverance is that it can't be stopped by anything besides death
  • James Stockdale
    • Knew as he was approaching the ground from his parachute that he would be captured and tortured but did not contemplate further. He (and John McCain who was there at the same time) cared about his cause and his men's well-being above his own
    • In every situation, no matter how dire it may seem, try to find the bigger picture and how your actions might be able to help others, loved ones
    • Pride can be broken. Toughness has its limits. But a desire to help? No
  • Michel de Montaigne
    • Nearly died falling off a horse but when he recovered he was a changed man and became one of the most prolific writers of his time
    • He became unequivocally aware of his mortality and decided to make the most of what he had. He was no longer afraid of death - looking into the eyes of death had been a relief, even inspiring
  • Death gives life meaning. Having that finite timeline pushes you and inspires you
  • Memento Mori - remember you are mortal
  • Knowing that life is a marathon and not a sprint is important. There will always be more obstacles but that is what makes life interesting. Behind the mountains are more mountains
  • When Marcus Aurelius was sick, Cassius rebelled and tried to become Caesar and instead of getting angry with him, he wanted to fight back and win but not kill Cassius or any of the conspirators in order to set an example of forgiveness for his troops and for Rome
  • Vires acquirit eundo - we gather strength as we go

In the Latticework, we've distilled, curated, and interconnected the 750+book summaries from The Rabbit Hole. If you're looking to make the ideas from these books actionable in your day-to-day life and join a global tribe of lifelong learners, you'll love The Latticework. Join us today.