Book Notes: The Obstacle Is The Way

The Obstacle Is The Way

Ryan Holiday

Published: 2014


Why I write book reviews, outlines, and reflections (link to bottom of page)


I read Ryan’s latest book Ego is The Enemy last year and loved it. I would describe it as philosophy in modern language, with great examples to illustrate the concepts, and written in a way that feels very practical to apply. I ordered The Obstacle Is The Way before finishing the other book, and pre ordered his latest upcoming release I was so impressed by it.


The Obstacle Is The Way is a modern version of Stoic Philosophy. I did not know of Stoicism before picking up this book – though I’ve taken a college level philosophy class I’ll admit it didn’t even ring a bell seeing the word on the page. Stoic philosophy I found out was practiced by philosophers as early as 300 BC and is. to paraphrase it, is separating logical reasoning from emotion. The biggest difference is that it’s advices are very practically applied as opposed to most philosophy being observations and understandings and not necessarily a usable guide to everyday life. As I learned in the book Marcus Aurelius, one of the most famous Emperors of Rome (who I’ll admit I only know because of the movie Gladiator), was one of the most notable Stoics in history and his writing is studied heavily on the subject.


Obstacle is the Way is basically broken up into three parts: Perception, Action and Will. Which is the steps one takes to both view, and turn obstacles into advantages. Ryan sets up the book explaining the concept we will be exploring, which is that obstacles are inevitable and that’s if we can suppress our basic emotions and reactions to these obstacles we would see that obstacles are advantageous to us, and that we should be thankful for the opportunities and lessons they create. In today’s world, our obstacles are more internal than external. In history obstacles like plagues, wars, and common disease set between us and our goals. Today the obstacles are more internal, things like stress, frustration, and debt. There are less threats that will kill us but plenty of obstacles nonetheless. Though the obstacles have changed the way great people react to them has not. Great people find a way to turn weakness into strength and to turn obstacles into advantages.


“The things which hurt…..instruct” Benjamin Franklin


Part 1: Perception

Ryan defines Perception as how we see and understand what occurs around us – and what we decide those events will mean. He then breaks it down into several brief chapters of advice to gain perspective on perception, and how to embrace it’s power in relation to obstacles.

  1. The Discipline of Perception
    1. Practicing healthy perception require exercise. If we are to keep our primal emotions and responses in check, we can stay calm in the face of adversity, and see the good in situation then we must practice doing so.
  2. Recognize Your Power
    1. No matter what situations arise, or how unfair things can be, we are never completely powerless. We control our mind and how we see obstacles.
  3. Steady Your Nerves
    1. Pressure and stress come with ambitious goals. As pressure mounts, grace and poise are more important than any other attribute because they are required if you hope to use any other skills.
  4. Control Your Emotions
    1. It’s ok to feel, but you need to separate emotional feelings from objective happenings (stoicism in a nutshell). Ryan calls is the “domestication” of emotions.
  5. Practice Objectivity
    1. Objectivity takes practice. Pull yourself out of the situation and work to see what’s really happening and see things for what they really are. This is an exercise which means it requires repetitions.
  6. Alter Your Perspective
    1. Ryan gives perspective two definitions
  7. Context – a sense of the larger picture of the world, not just what is immediately in front of us
    1. if you blow a meeting, realize it’s one meeting in a lifetime of meetings. As Richard Branson says “business opportunities are like buses; there’s always another coming around
  8. Framing
    1. an individual’s unique way of looking at the world, a way that interprets its events
  9. Is it up to you?
    1. We have to realize a distinction between what is up to us, and what is not. Focusing exclusively on what is up to us enhances our power. While chasing things that are not ours to change is destructive behavior.
  10. Live in the Present Moment
    1. Don’t overthink things. Practice living in the moment, working hard. 50% of businesses start in terrible environments without realizing it because they were busy living in the moment, and don’t realize their disadvantage until it’s in hindsight.
  11. Think Differently
    1. Our perceptions decide what we’re capable of. Stretch your perception of what is possible.
  12. Finding Opportunity
    1. See the good in everything. Start to view obstacles, rivals, setbacks for what they are: gifts. They make force you evolve, improve, realize what you don’t want, etc. Turn negatives into positives.
  13. Prepare to Act.
    1. Once you’ve managed your perceptions properly – you are ready to act with a cool head and steady hands.


Part 2: Action

Taking action isn’t special, taking the right action is what counts. When obstacles arise you can’t evade them, rely on others to solve your problems, or contemplate them to death – you must take directed action that supports your big picture goals and missions.

  1. The Discipline of Action
    1. Our instincts can cause us to be paralyzed in the face of obstacles, to simply wait for someone to fix things. Make a habit of running at obstacles, head on.
  2. Get Moving
    1. The timing is never perfect, someone might be trying to slight you, it might be too risky, it doesn’t matter – you must just start. Not doing, is the only surefire way to make sure nothing happens.
  3. Practice Persistence
    1. Expect problems but do not get distracted, discouraged or otherwise derailed from you goal. Each failure crosses one option off the list of what the solution is. Innovation comes by weeding through all the not-possibles to find the one way that is possible.
  4. Iterate
    1. Failure is inevitable. Expect it, enjoy it and learn from it. It’s often the source of breakthroughs. “Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over”.
  5. Follow the Process
    1. There are no big tasks, just big goals with tons of small tasks. “The Process” is breaking up those big goals into small tasks and putting your head down to complete each task with utmost quality. FINISH the task, and finish it well. Come up for air every now and then to check direction but trust and rely on the process.
  6. Do your job, do it right
    1. Our job is to try hard, to be honest, and to help others and ourselves. No matter what long term plans you have always excel with what you’re doing right now.
  7. What’s Right is What Works
    1. The conditions will never be perfect, a lot of times it’s far better to make the most with what you have than wait for the perfect opportunity that may never come. It’s better to make progress than try for perfection. Bend the rules, ask for forgiveness instead of permission – make things happen.
  8. In Praise of the Flank Attack
    1. Taking on a more powerful competitor head on is rarely the smartest way to approach a fight. Be guerrilla. Instead of pushing back against a competitor trying pulling after they have thrown a punch to use their momentum against them. True fatal weakness often comes when we (organizations) rely on size, strength or power. This strategy is much harder but that is why it works.
  9. Use Obstacles Against Themselves
    1. Sometimes you defeat obstacles not by attack, but by sitting back and letting them attack you. Moving forward isn’t the only way to progress – you can move sideways, and backwards. Deciding to resist action is action itself. This takes true humility but is effective.
  10. Channel Your Energy
    1. Don’t spend time focusing on all the “not-fairs” – channel your energy into your work. Be physically loose and mentally tight. Like an athlete in the zone – you don’t waste energy getting mad, or even celebrating.
  11. Seize the Offensive
    1. Truly gifted people view disaster as opportunity. A “teachable moment” waiting for you to seize it. When everyone else sees misfortune you see opportunity.
  12. Prepare for None of it to Work
    1. Somethings just won’t work out. You can do everything in your power but you can never control everything, and sometimes doing everything right will still leave you short handed. You can only put 100% effort into what you can control and affect, that’s it.


Part 3: Will

Ryan describes will as our internal power, which can never be affected by the outside world. And Will Power is turning undeniably negative situations into learning, humbling experiences that even help ourselves and others.

  1. The Discipline of will
    1. If perception and action are the disciplines of mind and body then will is the discipline of the soul. It is the only discipline that’s 100% in our control. We can form our perceptions and putt 100% effort into our actions but when things go wrong it requires will to endure and even be happy despite of problems.
  2. Build Your Inner Citadel
    1. A fortress inside of us that no external adversity can ever break down. We are not born with this, and it must be built and actively reinforced. We craft our spiritual strength through physical exercise, and our physical strength through mental practice – sound mind in a strong body.
  3. Anticipation (Thinking Negatively)
    1. The world is ruled by external factors. Be prepared for this. The only guarantee is that things will go wrong. The only things we can use to prepare for this is anticipation. Be prepared for failure and ready for success.
  4. The Art of Acquiescence
    1. Constraints in life are good. Accept them and let them direct you. When the cause of something is outside of us we are better off to accept it and move on.
  5. Love Everything That Happens
    1. Cheerfulness in all situations, especially the bad ones. We don’t get to choose what happens to us but we do get to choose how we feel about it.
  6. Perseverance
    1. Staying Power. It’s not about overcoming one obstacle but many. It’s not round 1 it’s the long game.
  7. Something Bigger Than Yourself
    1. When we focus on others our own personal fears and troubles will diminish. The desire to quit feels selfish when we consider the people who would be affected. Unity over self.
  8. Meditate on Your Mortality
    1. Remember you are mortal. You are not invincible and time is not limitless. Keeping your mortality in mind gives you purpose, urgency and perspective.
  9. Prepare to Start Again
    1. Behind the mountains are more mountains. Each time you learn something, develop strength, wisdom and perspective a little more of the competition falls away until all that is left is you: the best version of you.


Final Thoughts:

First see clearly. Next, act correctly. Finally, endure and accept the world as it is. It’s not enough to read or say this it takes repetitions of thinking and acting to turn it into muscle memory.



Why I write book reviews, outlines, and reflections:

I love to learn, and for me reading is one of my favorites ways to learn. In my quest for learning through reading I did some research on retaining the knowledge I am taking in to make sure it’s not “going in one ear and out the other” as we like to say. One of my methods of retention is taking notes, writing outlines to study, and recording my reflections and reviews of the information. I used to take a lot of physical notes, but seeing my book shelf full of books with folder papers sticking out the top is not only unattractive but also not a very scalable way to store information.  Now I’ve started transferring over my handwritten notes and highlighter filled books into digital format, and just in case anyone wants a quick read of any of the books I’ve read, or curious about someone else’s insight on a book they’ve read I decided to start publishing these notes.


Latest Article I wrote about reading:

Great Article about reading retention:


My Favorite Productivity Tools, Resources and Influencers

“If you love life, don’t waste time, for time is what life is made up of.” – Bruce Lee

I started studying productivity as a means to deal with the work load that progress and success brings. You plan for certain accomplishments but you don’t necessarily plan for the opportunities that come up along the way. At every level of success more opportunities present themselves and if you are driven person it can be hard to say no. Through time you are able to sharpen your abilities to follow new opportunities, but I quickly found myself with stack of so much “good stuff” that I really had to dig-in to be able to process everything. A reputation is built on delivering what you said you would deliver, or beyond it. Being a trustworthy person and more people speaking highly of you than having bad reviews. For those of us that like to accept new adventures or bite off more than we can chew, it’s so important that you have resources and systems in place to cope with opportunities or you risk under delivering and disappointing people that you worked hard to connect with or simply just adding hours and hours to your days. Sometimes it takes exceeding your maximum work capacity to understand that at some point you simply cannot do more. If you are to keep running at the pace you are running you there will start to reach a point of diminished return. In hindsight, I can draw together some basic symptoms from my personal experience.

  • Hearing a new idea from someone makes you want to run in the other direction as fast as possible. When you are over loaded, “new” sounds like death sentence. When you have your work under control, new ideas are fun and exciting.
  • You are constantly saying sorry. “Sorry it took so long to get back to you” “Sorry I missed your email” “Sorry I didn’t do what I said that I would.” When you are working like a dog nothing hurts more than having to say sorry all the time. You shouldn’t need to apologize for working so hard, but when you can’t cope with everything you have attracted or committed to you end up under delivering and feeling as if you are always on defense. When you have your work under control you can live on offense most of the time. Following up that someone received your work, calling contacts just to check in – not when they need something from you, happily answering the phone because you can process anything that comes in.
  • You feel like you’re constantly forgetting things. Unless you’re rain man, holding things in your head only works to a certain level.


If you recognize those symptoms, it’s probably time you start building systems. Whether you’re a lone ranger, have a personal assistant or are even in charge of a large staff it can still be very beneficial to have personal systems in place to cope with whatever is coming at you or even just to compartmentalize your thoughts and ideas. Here are 4 of the best tools I’ve found over the past 6 or 7 years, and what I’m currently using.




Getting Things Done. This is one of the most impactful books I’ve ever read.  I can clearly see a “before GTD” and an “after GTD” in my life. The philosophy of this book and the detailed systems you can apply to both your professional and home life are ridiculously awesome. I would recommend this book to just about anyone, ESPECIALLY entrepreneurs.

productivity post getting-things-done

David Allen

Not a huge surprise that I would list David Allen as my next resource, who just so happens to be the author of GTD that I just raved about. David is my favorite productivity authority, and following him online and in his other books is one of my favorite ways to keep my productivity work sharp.  I read and reread his book, and I would suggest signing up for his newsletter. I hope to one day participate in some of the coaching options he has available.

Productivity Post DavidAllen


Rescue Time is a cool tool you can install on your computer (and some phones.. I’m anxiously awaiting the IOS app to be available) that tracks how you spend your time. You simply install it and it runs in the background of your computer keeping track of what you spend time on. It auto-categorizes your activity and things it doesn’t automatically detect you can assign to different categories. This is a really cool way to analyze your productivity and make objective decisions about how you spend your time. I personally went on a mission to cut back both my time spent in meetings each week and time spent working out of my email inbox, and have really enjoyed the results of those changes.



Outlook Tasks

This is not a tool that I see many people using and now I live in it. I promise David Allen didn’t pay me to write this article, but David and the GTD team have a downloadable resource on the best way to track your to-do’s using Outlook Tasks. I’m a pen and paper kind of guy, but I try my best to transfer all my bad scratch notes into my tasks each day. Assigning them due dates, and even the locations on which I should work on them.

productivity post taks emoticon

Reading: whose doing it and who isn’t!

Reading statistics continue to drop, but it’s very clear that reading is one of the most common habits amongst successful people.

“Reading is to the mind what exercise is to the body.” —Richard Steele


I’ve always enjoyed reading. I don’t know if it comes from the days my mom used to read me the Hank the Cowdog before bed, or my childhood goal to read the entire Goosebumps series but I’ve always enjoyed it. I had a professor during my time at Oklahoma State University that encouraged his students to read 100 books. I love a good challenge and that goal has always stuck with me. I’m roughly 70 books into this endeavor, which I was initially proud of until I started to learn that a lot of people read 30-50 books per year.  Over the years, and a lot as of recently, I’ve been reading articles and studies that strengthened my view of the importance of reading, and I thought I’d compile some of the things I’ve found along with my own thoughts and put a piece together that I hope encourages at least one person to pick up book.

Who Is Reading?

I really like to find common denominators amongst people. People have been successful in a million different directions and endeavors but a common denominator amongst the most successful people in any area is that they read, and they read a LOT. Winston Churchill actually won his Nobel Prize in Literature. The founder of Nike had so much love for his library that he would make guests remove their shoes to enter. Warren Buffet has been reported to ready nearly 1000 pages per day, spending more than 80% of his time reading. Buffet said “That’s how knowledge works. It builds up, like compound interest.” Bill Gates reads roughly 50 books per year. Mark Cuban has been said to read over 3 hours per day.

There are no treasure maps or magic pills that will get you the success and happiness that you desire but it seems obvious to me that the more you read, expand your knowledge base, build your capacity to understand concepts, and learn by example the more likely you are to find what you’re after. You can’t say that reading makes people successful but the evidence certainly points towards reading being one of the biggest differences between the successful and unsuccessful.

Whose Not Reading?

There’s a very popular study that was done in 2003 by the Jenkins group that released some very scary statistics. They claimed that 1/3 of all US High school graduates would never read another book after graduation and that 42% of all College graduates would never read another book after graduation. The Harvard Business Review also released a statistic that for the first time in US History that less than 50% of the population currently reads.  It should be noted that this study is quite controversial and many people have published articles about its falsity. For the purpose of my points however the exact numbers aren’t really that important – while the Jenkins group produced the most alarming figures, there are plenty of stats out there that when simply put prove: People (namely Americans) are reading less and less.

I find this very scary for a few reasons. The first thing that comes to mind is the philosophy that if you aren’t learning then you’re regressing. I don’t think that reading is the only way to learn – you can of course learn from experience, from person to person communication, from video or television, etc. but at the heart of any deep learning is usually the study of written material. If there are more people regressing than progressing, that spells trouble for us! The next thing that comes to mind is that much of our future planning and innovation comes from a respectful understanding of the past and those that came before us. It’s a tragedy for people not to build on each other’s knowledge base and advance the world with each generation. The less we read and understand those before us I think the less likely that we will move forward with much significance. As an individual I can’t understand why so many people would not want to read more out of pure curiosity. It’s easier than ever before to use search engines to answer our questions, and there’s not a lot of things that you can’t find a quick tutorial for on YouTube but to gain deep understanding it’s hard to beat reading well written books on topics of interest. Just walking into a library and seeing a visual reminder of how much knowledge is sitting on the shelves is amazing to me. You can learn business, medicine, philosophy all with some concentrated effort to absorb what’s been written for us.

Globally literacy rates are improving as we as a human race work to educate more and more of the world. But still it’s estimated that 1 Billion people cannot read or write their name.  There are hundreds of articles across the internet that directly link illiteracy with poverty, incarceration, and even life span. Teaching someone to read is one of the biggest gifts you can give someone. When you flip the perspective, of reading from something you must do, or should do, to something that 1 Billion people don’t have the privilege to do it, really makes you think. Or if you consider the time when the Nazi’s were burning books that challenged their philosophies – makes you realize we take for granted that we can order any book about any topic from Amazon and have it in our hands in a couple of days. There have been people in history that have risked their lives to read, and others that have every opportunity and simply choose to do something else.


What to Read?

The obvious next question is what should you read? While I think the question of “To read or not to read” is a very easy question, I honestly don’t think that question of “what to read” is as important. I got to listen to Carl Sewell speak attending a college graduation for a friend at SMU. Carl said that he aims to read a nonfiction book to build his knowledge base every 6 months, a biography in between those books, and reads for pleasure about current events daily. I have read that some top CEO’s actually read fiction more often to help expand their creativity during their hectic tenures at the top of big companies. There have also been studies done where a surveyed group of successful entrepreneurs said that they felt that reading books across multiple disciplines led to innovation. Benjamin Franklin is one of history’s biggest influences in many areas, and the area of self-improvement is no different. Franklin used to break his self-improvement efforts into 13 week cycles, choosing an area of focus for each 13 week segment and rotating through 4 segments per year.

I personally divide my reading up into categories but I try not to be too strict on myself. I use the GoodReads app to keep track of all the books I’ve read and plan to read. Each time I finish a book I’ll usually decide if I want to continue on the path related to the book I just finished or I’m ready to switch gears and learn something new. I also like to rotate in some fiction books from time to time because I think allowing your mind to get lost in a story is important, it’s fun, it expands your imagination and I also end up learning quite a lot reading fiction. For instance reading Grisham books has certainly increased my knowledge of the legal system, and often the setting of a book gives you a new awareness of the city or region that the book takes place in.

Want to see my list or connect so I can see what you’re reading list looks like? Add me on GoodReads!


Read, read, read. —William Faulkner

Reading is important, because if you can read, you can learn anything about everything and everything about anything. —Tomie dePaola

He that loves reading has everything within his reach. —William Godwin

Once you learn to read, you will be forever free. —Frederick Douglass





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