The Best Notes From: “The Obstacle Is The Way”, by Ryan Holiday

Familiarize yourself with the Stoic philosophers, and let their ways of thinking become your own. I can’t emphasize enough the fact that really internalizing their messages is absolutely crucial to developing godlike levels of self-discipline. Constant peace of mind is their gift to you as well.

Image for post
Image for post

I first read “Meditations” by Marcus Aurelius in 2015, and it quickly shot up to be one of my favorite books of all time.

Page after page, it became abundantly clear that I didn’t have to remain a passive object, thrown about by the vicissitudes of life and death. External circumstances held no more terrifying power than a light breeze on a September afternoon.

Nothing could reach the inner citadel, into which my mind was transformed.

That book, and others by the Stoics fortified my mind to such an extent that I would never have become the confident, disciplined, principled individual that I am today if I hadn’t first been exposed to their teachings.

Ryan Holiday, another fan of the Stoics and what they have to teach us all, came out with a phenomenal little book, called “The Obstacle Is The Way”. He distills many thousands of pages of Stoic thought into a very handy compilation of advice, strategies, and anecdotes, and places reality squarely before your eyes.

I read this book in 2015 as well, and I heartily recommend it to anyone who is interested in learning more about this stunning, powerful philosophy of enduring hardship with only the resources that already reside within us.

My notes here don’t even really do justice to how empowering a philosophy Stoicism really is.

Some Notes on Note-Taking

For every single book that I read, I take notes on everything that I want to remember. One year, I read 170 books, and another year ‘only’ 39.

I absolutely have to take notes because I will never, ever trust my memory. I just read too much. If you take a look at my reading list, you’ll see that there’s just no way that I would be able to remember even 10 notes from each book. My advice: “Write it down!!!”

I never intended to sell these notes, or try to imitate SparkNotes, so some of my notes may go further in depth than some professional book summaries, and some not so deep at all. These aren’t something you might find from Blinkist, or even from James Clear, or Derek Sivers. They were never meant to be.

Image for post
Image for post

They are simply what I have personally taken from each book, and I hope that they have some value for you.

That being said, many of these notes are from some of the most important books ever written.

I’m interested in the human condition, the biggest questions ever asked, and the giant mystery that we’re all a part of. I’m interested in nothing less than what constitutes a meaningful life. That’s what you’ll find within my multiplicity of notes and sources.

Remember to think critically! Some notes are just interesting ideas taken from the text that I may or may not agree with.

Regardless, I wanted to remember them so as to stimulate my thinking at a later date. So don’t confuse my notes here with something that I staunchly believe. Sometimes you’ll be right, and other times you’ll be wrong. So it remains important to think for yourself and come to your own conclusions.

I have turned them into a product which I sell in return for donations to Doctors Without Borders.

But I’ve decided to release some of my notes periodically on my site, for free.

So let’s get to it…

From Amazon: The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do.

Image for post
Image for post

Its many fans include a former governor and movie star (Arnold Schwarzenegger), a hip hop icon (LL Cool J), an Irish tennis pro (James McGee), an NBC sportscaster (Michele Tafoya), and the coaches and players of winning teams like the New England Patriots, Seattle Seahawks, Chicago Cubs, and University of Texas men’s basketball team.

The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.”

Ryan Holiday shows us how some of the most successful people in history — from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs — have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck.

If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era.

My Personal Notes From “The Obstacle Is The Way”:

Lesson: This is straight from Marcus Aurelius. It’s probably one of the most famous quotes from the book, and it’s a “Joe Frazier Left-Hook” to the mouth of all of your excuses. We have this incredible power to choose our own attitude in any given situation. We give up our power when we let external events dictate to us how they are going to make us feel. If, in your own mind, you don’t feel like you’ve been dealt a negative blow, then you haven’t been. Remember this.

Lesson: We can always do SOMETHING. There will never be a time in your entire life when you will be unable to take some sort of action, mental or physical, to reduce your suffering, or the impact that your suffering has on your mental state. Don’t even entertain the notion that you’re completely powerless because you’re just lying to yourself. You’re letting yourself down, and as a man or woman of personal integrity, you are going to avoid that at all costs.

Lesson: There is a world of difference between things that are simply unlikely to happen, and those that will never happen regardless of how hard anybody tries. For example, it’s unlikely that I will ever become fat. I just care too much about my body, my physical appearance, and my health to ever let that happen. But…it’s still possible in the very distant future. However, am I ever going to be President of the United States? No! Because of, well, reasons. There is unlikely, and then there is impossible. Take a good hard swing at unlikely outcomes every once in a while.

Lesson: This means exactly what it says it means, and I’m not going to belabor the point. Every gets frustrated at some point, and everyone wants to give in when they’re not seeing the results that they so earnestly expected. That’s fine. What’s not ok is just slinking off into the night, defeated and depressed. Is that what having godlike discipline is about?

Lesson: Energy keeps coming back to you, day after day. If you run out one day, there is another day coming up right behind it which will find you back to the energy levels at which you started. Or, depending on how you’ve been taking care of yourself, you’ll have even more energy as time goes on. Being tired at the end of the day doesn’t mean that it’s all over; every day is part of fighting the good fight.

Lesson: Nobody learned anything from succeeding all the time. It’s challenges which put us on the defensive and force us to engage intelligently with what we are facing. When you’ve failed, you’ve found a way that didn’t work. You’ve found out some person’s true nature, you’ve learned something that you didn’t know before that’s going to help you next time. These are just words on a website; it’s much harder to actually go out and commit to being ok with failure. But every failure contains the seeds for new success, and vice versa.

Lesson: The most important thing right now is to figure out what the most important thing is right now. No one expects you to have all the answers at the outset, and if you do, then man…this must be pretty boring for you! Take one correct action, then a second correct action, and then a third. Actually forget “correct”; just take a meaningful action. Over and over and over. Again and again and again.

Lesson: See that cartoon of the diamond-mine worker? It’s a cross-section, showing him toiling away and getting frustrated enough to quit. And then on the other side of where his pick-axe was hammering away, maybe 6–12 inches away, is a massive diamond deposit that’s even bigger than he is. A few more hacks and the thing would have been busted right open. But that miner is like a lot of us. We give up, we stop hammering away, when in fact we were so close to achieving that breakthrough that we’ve been dreaming of. Don’t let this happen to you!

Lesson: Anybody can resist fatty foods when they’re full. Anyone can be nice to people who are being nice to them. It’s when things aren’t going our way that we need an empowering philosophy like Stoicism to guide our path. We fill ourselves with these thoughts while things are going well, in the good times, so that when adversity strikes, we have done the roadwork already. We’ve fought the fight a thousand times in our minds. We’re ready.

Lesson: The universe was absolutely NOT designed with the comfort of human beings in mind. It doesn’t give a damn about your safety and security, and it’s not your friend. You can accord with it, you can be grateful for it, it can bless you, but it’s not going to make things any easier on you than it does for the rest of humanity. You have to be ok with this, and focus on what you DO have some modicum of control over, which is the strengths that YOU possess. You can’t change the rules, but you can become a better play.

Lesson: As they say, we are living amid the causes of death. Accidents, diseases, misfortune of various kinds…they’re everywhere. I don’t think I have to try and scare you into believing that we are, at every moment, perilously close to death. Yet we think we have so much time; we think that all those things can’t get to us. But if you remind yourself how fragile your life actually is, you’ll appreciate the time you have right now, and you’re not going to let all those little things bother you like they once did.

Lesson: Building on the above, death forces everything into focus. I remind myself in the morning, before bed, and various times throughout the day that I am living on borrowed time. I am not even guaranteed tomorrow, just like I wasn’t even guaranteed the today that I am so grateful for. So what’s left to us? We can appreciate the people we love, we can do the stuff we’re passionate about and love doing more than anything else, and we can be cool to each other. Most other things are superfluous garbage.

Lesson: When you accomplish one thing, it becomes “What else can I accomplish?” More opportunities for challenges, growth, and temporary defeat await our every advance. Once we tackle one initial challenge, more will spring up. But we will have prepared by the most effective means available to us. We will have prepared by defeating the last thing that thought it could beat us.

Lesson: Human beings need something to struggle against. This idea of retirement on the beach somewhere will get boring in about a week and a half. That is, if we’re not constantly challenging ourselves to do more, and become more. It doesn’t “end” until we die, and then, who knows. The Stoics weren’t concerned with stuff like that though. They urge us, from thousands of years ago, to show up, advance confidently in the direction of our dreams, and hammer away at those obstacles until either they fall or we do.

Image for post
Image for post


Stoic thought has been a mainstay of my life for quite some time, and I don’t imagine that I’ll ever stop reading, and re-reading those notes, and the phenomenal books that they came from. Seneca, Epictetus, Marcus Aurelius; these are all names with whom I urge you to become intimately familiar.

Ryan Holiday has really done a fantastic job at distilling all this ancient wisdom and leaving us better off than he found us. I thank him for taking the time to write such an urgently needed book.

And because self-discipline is an expression of our own will, we all have the power to choose how we show up in the world. It’s my hope that you will execute that power.

I hope these notes sparked your interest, or led to some new questions, or just made your life better in some way.

If they did, I’d love for you to consider donating to the phenomenal international non-profit, Doctors Without Borders. We operate all over the world, proving free medical services to those hardest hit by war, famine, and other disasters and atrocities. We never discriminate on the basis of gender, religion, ethnicity, etc. And we would be honored to receive your support.

All the best,

Matt Karamazov


The Obstacle Is The Way — Goodreads

Author Website — Ryan Holiday

Meditations — Marcus Aurelius

Receive More Articles Like This One


Matt Karamazov is a human rights activist, boxer, and writer who reads at least 100 books every year and throws 300 punches per minute. His website, Godlike Discipline, is dedicated to raising money for causes like Doctors Without Borders, and Human Rights Watch, among others. It’s also dedicated to helping people tackle their biggest willpower challenges. He also like death metal, and so, consequently doesn’t get many second dates. Here he is on a horse.

Image for post
Image for post

Written by

Top Writer in Books and Reading. Physique Competitor. Nonprofit Leader. Best Books:

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store