The Obstacle is the Way book Summary and PDF

The Obstacle is the Way by Ryan Holiday [BOOK SUMMARY & PDF]

The Obstacle is the Way is a fantastic and instructive read all about how to overcome any obstacle or challenge and turn it into an advantage. From author Ryan Holiday, The Obstacle is the Way draws on key historical figures and stoic philosophy to communicate its message. No matter what background you come from, your area of expertise or goals for the future, everyone can learn a valuable lesson from this book.





Who is this summary for?

The Obstacle is the Way is a fantastic and instructive read all about how to overcome any obstacle or challenge and turn it into an advantage. The Obstacle is the Way draws on key historical figures and stoic philosophy to communicate its message. No matter what background you come from, your area of expertise or goals for the future, everyone can learn a valuable lesson from this book.

About the author

Ryan Holiday considers himself a writer and a media strategist. With 6 books under his belt and an extremely successful blog, Ryan has covered a lot of topics surrounding personal and business development. He has a passion for philosophy & stoicism as well as marketing, business, success, growth, marketing, self-awareness, and learning. Ryan follows on from The Obstacle is the Way with Ego is the Enemy; where he explains why we mustn't let our ego's become a controlling factor in the way we act and make decisions. Ryan studied under Robert Greene, author of The 48 Laws of Power and credits a lot of his success and strategies to Greene.

In this summary

Ryan breaks his book into 3 parts; Perception, Action & Will. This summary will discuss each of these 3 parts in-depth and hopefully, you will walk away with a better understanding of how to handle ‘obstacles’.



”Perception is how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness.”

What to keep in mind

Ryan recommends that you keep the following things in mind when you face an obstacle, it’s important to always try to;
– Remain objective
– Control your emotions
– See the good in situations
– Calm your nerves
– Remain ignorant of what disturbs or limits other people
– Try to keep things in perspective
– Only focus on things within your control
– Be in the present

According to Ryan, if you can follow these steps, this will allow you to see what opportunities arise within whatever obstacle you are facing. If you don’t follow these steps, you let the obstacle overcome you, the opportunities are over-shadowed and often missed. The process requires a lot of self-discipline but is always worth it.

'Our perceptions can be a source of strength or of great weakness.'Click To Tweet

You have power within

Ryan discusses that the way we perceive events and obstacles is significant. We play a major role in both the creation and the possible destruction of any obstacle that we face.

The realist is, that there is no concept of good or bad in this world, they only exist within us. Our perception of events and things as either good or mad are what cultivates the meanings. In simpler terms, it’s up to you to assign meaning to any specific event or obstacle you face. The meaning isn’t there until you prescribe it.

Ryan explains that other people may tell you that the situation you are facing is hopeless, that something is ruined or broken. But it’s up to you to remain objective and apply your own perception and meaning to the situation. Ignore what other people perceive and don’t let them influence you.

”We decide what story to tell ourselves. Or whether we will tell one at all. Welcome to the power of perception. Applicable in each and every situation, impossible to obstruct. It can only be relinquished. And that is your decision.”

Are you nervous?

”Regardless of how much actual danger we're in, stress puts us at the potential whim of our baser—fearful—instinctual reactions.”

The key is to reign in any feelings of nervousness. Remain calm in situations and don’t allow yourself to feel any fear. If we can act with nerves of steel, we are going to be in the best situation to tackle the reality of the situations. Nerves are only going to get in the way and cloud your judgment, make things seem worse than they perhaps are.

The next thing to tackle is your emotions. Ryan acknowledges that when facing a stressful obstacle, it’s easy to let your emotions get the better of you. But this is exactly when you need to get a handle on them.

Ryan suggests you have the following conversation with yourself in order to get a better handle on your emotions in stressful times;

”Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?Nope – Then get back to work!”

Continue to ask yourself if you really need to freak out about the situation, or if it’s less of a big deal. Ryan suggests constantly checking in with yourself and assessing your emotions.

Time to be objective

”The phrase “This happened and it is bad” is actually two impressions. The first—”This happened”—is objective. The second—”it is bad”—is subjective.”

Ryan explains objectivity as removing the “you” (the subjective) from any situations. Imagine that you aren’t involved, if someone else was facing the same obstacle, what advice would you give? Often, when you are removed from the situation, the solution becomes clear-cut and obvious. This is why we are often so good at helping other people and offering advice, but not so good at doing it ourselves. Practice being objective whenever you can,

If you face an obstacle, take yourself out of the situation and pretend it’s happening to someone else and it’s not that important. Consider the advice you would give, more often than not you will be able to assess the situation clearly, consider the options and decide how to tackle it. All of this can be done with limited nerves and emotions when you have taken the “you” out of the situation.


Ryan explains that perspective has two definitions;
1. Context: a sense of the larger picture of the world, not just what is immediately in front of us.
2. Framing: an individual's unique way of looking at the world, a way that interprets its events.

The key is to acknowledge the difference between the right and the wrong perspective. Your perspective is the tool that you use to interpret any event or situation in your life. It’s the reason you see things as good or bad.

”Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”

Is it all on you?

Ryan’s a big fan of stoicism, and he uses the Serenity Prayer, a two-thousand-year-old stock phrase to explain what you need to worry about, and what you can ignore.

””Ta eph'hemin, ta ouk eph'hemin.” – What is up to us, what is not up to us.”

Ryan considers the following things to be “up to us”
– emotions
– judgements
– creativity
– attitude
– perspective
– desires
– decisions
– determination

The rest is not up to us. There are so many factors that you cannot control, and these are what you need to ignore, take the pressure off and only focus on what is “up to us.” Ignore the weather, economy, other people’s opinions etc.

When you are facing a situation or an obstacle, it’s absolutely critical that you assess what factors are within your control, and these are the ones you can focus on. Ignore anything outside of your control, what’s the point of worrying about something you’ll never be able to change?

”That's the difference between the people who can accomplish great things, and the people who find it impossible to stay sober—to avoid not just drugs or alcohol but all addictions.”

Be Present

Ryan encourages you to always be present in the current moment, whether that be a really bad time or a really good time, whether you're facing an intimidating obstacle or experiencing a joyful time. The thing to remember is to live in the now. Be aware of what is happening around you right now, acknowledge the current circumstances and embrace them.

”The implications of our obstacle are theoretical—they exist in the past and the future. We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.”

If you're facing a troublesome obstacle, Ryan encourages you to consider it an opportunity to really focus on the present. Ignore the ‘big picture’ of the troublesome obstacle and make peace with the what happens, as it happens. There’s no point worrying about an event before it’s happened, or dwelling on it once its over. Trying to make predictions for the future isn’t benefiting you, let it happen naturally and let each moment wipe the slate clean.


Ryan uses an example of a study done by sports psychologists on elite athletes who were facing serious injury and/or adversity. Athletes initially responded with feelings of isolation, being overly-emotional and questioning their own athletic capability. However, after recovery, the athletes expressed a new perspective, they came to realise their own strength and they often gained the desire to help others. Ryan explains, that the results clearly identify that the doubts, fears, and concerns the athletes felt initially actually helped transform them into better athletes, better people and stronger mentally.

Psychologists refer to this as adversarial or post-traumatic growth. The concept of “that which doesn’t kill me makes me stronger.”

Ryan explains that it’s about seeing the obstacle as an advantage, allowing the struggle to only strengthen us. Don’t let your perception of the situation cloud the opportunity.

”This is the one strategy you can always use. Everything can be flipped, seen with this kind of gaze: a piercing look that ignores the package and sees only the gift.”

Prepare to Act

”Problems are rarely as bad as we think—or rather, they are precisely as bad as we think.”

An interesting insight from Ryan is that the event itself is never actually the worst thing to happen. The worst thing to happen is you’re reaction, the way you cope.

”The demand on you is this: Once you see the world as it is, for what it is, you must act. The proper perception—objective, rational, ambitious, clean—isolates the obstacle and exposes it for what it is.”




The second section of The Obstacle is the Way is dedicated to ‘Action’. Ryan talks about action as a discipline, directed action rather than any random action. He explains that the only way to tackle the obstacle your facing is to break it down, step-by-step, action-by-action. You have to be persistent and constantly putting one foot in front of the other in order for your actions to pay off.

It’s a discipline

”We forget: In life, it doesn't matter what happens to you or where you came from. It matters what you do with what happens and what you've been given. And the only way you'll do something spectacular is by using it all to your advantage.”

Ryan recognises that we consistently complain about our situation, we are either too tired, stressed, busy, overweight, time poor. And what do we do about it? Nothing, we continue to do the same thing and we receive the same results.

It’s easier to ignore these things, but really we know that we can never expect any improvements unless you act. And you have to start immediately, stop putting it off.

Ryan suggests that we face our obstacles with the following;
– energy
– persistence
– deliberate processes
– resilience
– pragmatism
– strategic vision
– savviness
– an eye for opportunity
– craftiness

Get Moving

“We must all either wear out or rust out, every one of us. My choice is to wear out.”

The only way you are ever going to improve your situation and actually reach your goals is if you stop sitting still, stuck in the same cycle. You need to act, get moving and pursue your dreams and goals.

If the conditions aren’t ‘perfect’, or you don’t feel ready, that’s no excuse. There’s barely ever a ‘perfect’ time to get started. How many of us wait until Monday to start a diet or exercise routine. Whats the harm in starting now? Create momentum and get moving.

Be Persistent

There are times when you are going to feel discouraged. And Ryan says that’s OK. But, he says it's NOT OK to quit. When you feel like quitting, you have to find a persistence within you to keep moving forwards. Never backward.

Ryan explains this with the example of Thomas Edison’s invention of the light bulb. The common assumption is that he had an epiphany, a flash of genius and realisation, and invented something so significant. But the reality is that the process was slow and steady, practiced over and over and over again. With the eventual reaching of the end goal. It certainly didn’t happen overnight, there were setbacks. But, he was persistent.


Ryan uses Silicon Valley start-ups as an example to teach us a lesson in adaptability. When they are working on a product, start-ups release what they call their ‘MVP’ (minimum viable product). This is essentially a very basic version of their business model concept, often with only one or two of the overall features.

The reason the release their MVP first is to gauge the reaction. They want to see how customers react to the basic model before they move on to their final product. This avoids big investments into things that may not be marketable.

In Silicon Valley, start-ups don't launch with polished, finished businesses. Instead, they release their “Minimum Viable Product” (MVP)—the most basic version of their core idea with only one or two essential features.

The point is to immediately see how customers respond. And, if that response is poor, to be able to fail cheaply and quickly. To avoid making or investing in a product customers do not want. And with each MVP released, and each round of feedback and responses from customers gives them the opportunity to adapt and improve their product. The feedback may be negative, but they can use it as a positive.

”Being able to see and understand the world this way is part and parcel of overturning obstacles. Here, a negative becomes a positive. We turn what would otherwise be disappointment into opportunity. Failure shows us the way—by showing us what isn't the way.”

'Failure shows us the way—by showing us what isn't the way.' Click To Tweet

Follow the Process

”The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.”

Ryan acknowledges that you’re more than likely facing a difficult situation and difficult tasks. But there’s no time to dwell on just how difficult it’s going to be. The key is to break it down into little bits, little tasks you can tick off one by one. Focus on the first step first, do it well. Tick it off and move onto the next.

“Follow the process and not the prize.”

Do Your Job & Do it Right

You’re responsible for your actions, so it's important to make sure that whatever it is your doing, you’re doing your very best. Ryan discusses the importance of this at every single level. Whether it’s an after-school job to save some money or a well-qualified law position. Everything you do matters, so make sure you do your best at it.

”Wherever we are, whatever we're doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That's our primary duty. And our obligation. When action is our priority, vanity falls away.”

Ryan points out that the reality is that you’re most likely going to do many different things in your life, and you may not love them all. Some may be beneath you, and others will be so prestigious that you’ll feel out of your depth. But it’s your duty to approach every job with the same attitude, to give it your absolute best.

“Don’t go expecting Plato’s Republic”

Ryan brings it back to stock philosophy with this saying. And his point is that you can search endlessly, but you’re never going to find perfection. Perfect doesn’t exist, you’ve got to work with what you’ve got.

The example of the first iPhone exemplifies this point well. Ryan explains that the very first iPhone didn’t have a copy-and-paste feature. And there were other features missed out. Steve Jobs and Apple had a reputation for perfection, but they had to compromise on certain features, in order to get the product out there. There is never a perfect, there’s always going to be something that could be improved. What mattered most is that they built a beautiful product that people loved.

”Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don't think small, but make the distinction between the critical and the extra. Think progress, not perfection.”

Ryan explains that when you face an obstacle or a difficult task with this attitude, the obstacles will break apart. You’ve made them completely irrelevant, meaningless, so you are free to tackle them as you please.

If you’re approaching from behind…

“Being outnumbered, coming from behind, being low on funds, these don't have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle.”

Here Ryan’s talking about looking for the good in bad situations, using them as opportunities to propel us forward rather than letting them overcome us. Ryan explains that when companies or people who have always had the size and power behind them, have never really learned how to progress themselves, they simply ‘coast’ along on that path that was laid for them. SO even though it may seem hard at the time, you’re going to be better off in the long run. Face these disadvantages head-on and refuse to let them ruin you, challenge them and from there you will grow!

Use the obstacles

Ryan explains that sometimes if you step back and let the obstacle attack you, you can actually use the obstacle against itself and come out with a positive.

”Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive.”

This, Ryan states is a concept that should bring you great comfort. It means that no matter what the obstacle is, it will unlikely ever be too big for you to handle. In some cases, the bigger the obstacle, the better, when using it against itself. Ryan uses the metaphor of a castle, explaining that it can be an intimidating, impenetrable fortress when viewed from the outside, but when the enemy surrounds it, it transforms into a prison to those inside. All it takes is a shift in perspective and plan of attack.

'Every positive has its negative. Every negative has its positive.'Click To Tweet

Channel Your Energy

”Think of an athlete “in the pocket,” “in the zone,” “on a streak,” and the seemingly insurmountable obstacles that fall in the face of that effortless state. Enormous deficits collapse, every pass or shot hits its intended target, fatigue melts away. Those athletes might be stopped from carrying out this or that action, but not from their goal. External factors influence the path, but not the direction: forward.”

Ryan discusses why we shouldn’t give in to frustrations that we meet, if we can work to channel these frustrations we can actually use it positively. Ryan explains that we can use this to actually power our actions, which consequently, become stronger & better when they are loose and bold. Ignore everyone else who observes the rule, be the one who undermines them and uses it to your advantage.

”To be physically and mentally loose takes no talent. That's just recklessness. To be physically and mentally tight? That's called anxiety. It doesn't work, either. But physical looseness combined with mental restraint? That is powerful.”

It’s all about the offense

Ryan acknowledges that it’s a guarantee, that throughout your life you will face periods of frustration, things will appear to be unfortunate or unfair. Ryan points out that more often than not, you're facing these times when you need them the least. However, Ryan poses the question; “do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive?”

In other words, can we take the problem and see it as an opportunity. Is there an answer here that you’ve been looking for all along? Any obstacle that you meet can be seen in either light, it’s up to you to face it with confidence and attack it the best way you can.

”The obstacle is not only turned upside down but used as a catapult.”


”Perceptions can be managed. Actions can be directed. We can always think clearly, respond creatively. Look for opportunity, seize the initiative. What we can't do is control the world around us—not as much as we'd like to, anyway. We might perceive things well, then act rightly, and fail anyway.”

A point that Ryan makes in this section is that nothing can actually prevent you from trying. You can always make an attempt. And you may try and try and try, but the obstacle you are currently facing may just be impossible to overcome. That’s life, it’s not even a bad result. And even if the only outcome of the event is that you learn to accept that sometimes, bad things happen, and you learn a little bit of humility.

”We have it within us to be the type of people who try to get things done, try with everything we've got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.”




Ryan describes will as an internal power. It’s something that you have complete control over and no external sources can really affect it.

”If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.”

It’s a discipline

So far Ryan has taught us how to think and act, will is the final piece of the puzzle. Will is there to prepare you and protect you from the unpredictability, it’s there to increase your happiness and allow you to grow and thrive. As the final discipline, Ryan explains that it’s actually the most difficult to master. Where others will easily give into the conditions, you have to learn how to channel your will to keep you calm, confident and strong enough to battle on regardless.

”It's much easier to control our perceptions and emotions than it is to give up our desire to control other people and events. It's easier to persist in our efforts and actions than to endure the uncomfortable or the painful. And it's easier to think and act than it is to practice wisdom.”


Ryan explains that it doesn’t happen overnight, you have to build this strength within and it’s going to take time. But once it’s established, you’ll be able to achieve your goals despite any obstacles that you may face.

Anything worth achieving is going to take practice and patience. You’re not going to get it perfect on the first go, but the lessons you learn are all part of the growing process.

”It's almost a cliché at this point, but the observation that the way to strengthen an arch is to put weight on it—because it binds the stones together, and only with tension does it hold weight—is a great metaphor.”

Ryan explains that you simply cannot afford to shy away from the things you fear or anything that intimidates you. You don’t have to be weak, you can be strong, confident and calm.


Ryan acknowledges that it’s impossible to have complete control of your life, there are always going to be external factors that greatly affect you. And things aren’t always fair, you may not always get what you earned or what is rightfully yours. But the key is to anticipate these factors and be prepared.

If you let yourself be consistently surprised and taken aback when things don’t quite go to plan, you’re going to open yourself up to a lot of heartache and suffering. Every time something unexpected happens your going to feel beaten and weaker. Ryan points out, that despite being a very glass-half-empty perspective, the only thing you can truly guarantee is that things are going to go wrong. And the best way to combat this is to anticipate them and prepare ourselves. We are the only variable in the events that you have control of.

Allow yourself to understand the different scenarios that could occur, there’s always going to be more than one potential outcome, some good and some bad. Understand all the angles and be prepared for any of the outcomes.

Robust & Resilient

Ryan uses a metaphor about traffic to explain his next point. You can’t take red lights personally, can you? Or if you’re driving home and the main intersection has a major blockage that delays you for an hour. Although inconvenient, the traffic isn’t out to get you. And there’s nothing you can do about it. You can’t make it go away any faster. You have to accept it.

Ryan suggests you take this approach when facing other obstacles in your life. Because;
“(a) you're robust and resilient enough to handle whatever occurs,
(b) you can't do anything about it anyway, and
(c) you're looking at a big-enough picture and long-enough timeline that whatever you have to accept is still only a negligible blip on the way to your goal.”

Love it all

”We don't get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good? We can choose to render a good account of ourselves. If the event must occur, Amor fati (a love of fate) is the response. Don't waste a second looking back at your expectations. Face forward, and face it with a smug little grin.”


Ryan defines persistence as the attempt to solve a difficult problem, with determinations, and trying until it’s broken down. But perseverance, he describes, as something bigger. He explains that perseverance is about the long-haul, it’s all about every single round of the fight, the pure determination of facing every single obstacle and still be fighting until the very end.

”Life is not about one obstacle, but many. What's required of us is not some shortsighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.”

Ryan explains that persistence is simply the action, whereas perseverance is all about will. It’s endurance rather than pure energy. And obviously, when used in conjunction, the results will always be positive.

It’s not all about you

It’s easy to have tunnel vision when facing a certain situation. Asking yourself why it happened to you? What are you going to do next? But really, the key is to take a step back and look at the bigger picture. How can the situation you are currently facing actually benefit someone else? Can you use it to teach a lesson? What about others who are facing similar situations, can you help them to?

And just like that, Ryan explains that your problem becomes part of a larger whole, there can be a sense of community and together you can feel stronger. The old saying goes, a problem shared is a problem halved. And this rings true here.

”Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We're all just humans, doing the best we can. We're all just trying to survive, and in the process, inch the world forward a little bit. Be strong for others, and it will make you stronger.”

Acknowledge your mortality

Another slightly morbid topic but something that Ryan acknowledges is our own mortality. It helps you form your perspective and in some cases create a sense of urgency. Rather than ignoring or denying our mortality, embrace it, recognise that we only have a short time to live and use that notion to live the best life you can.

”It doesn't matter who you are or how many things you have left to be done, somewhere there is someone who would kill you for a thousand dollars or for a vile of crack or for getting in their way. A car can hit you in an intersection and drive your teeth back into your skull. That's it. It will all be over. Today, tomorrow, someday soon.”

Prepare to Start Again

We live in a constant cycle of facing obstacles and overcoming them only to be faced with the next one. But if life didn’t continue on this way, it would be boring, mundane and stagnant. It’s these events that create opportunities. Each time you have to navigate an obstacle, you learn a little bit about yourself and others. You can take your new-found knowledge and use it the next time.
Ryan explains that the more obstacles you face and overcome, the more you develop strength, wisdom, and perspective. And you’ll continue improving yourself.

”Passing one obstacle simply says you're worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt.”

“See things for what they are.

Do what we can.Endure and bear what we must.

What blocked the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.”


Key Takeaways

  • You can manage your own perceptions and impressions.
  • You have the ability to take negative situations and see an opportunity.
  • The ability to direct your actions is within you, you have control over what you do in response to any obstacle.
  • Will is within you and can be trained to be great and powerful.
  • Practice patience, and learn from mistakes.
  • Be persistent and persevere.
  • You are capable of overcoming obstacles and turning them into opportunities.
  • Acknowledge your own mortality so that you can live your best life.

Further Reading

Other reads by Ryan Holiday include Ego is the Enemy – a very complimentary continuation on from The Obstacle is the Way that focuses on how when on the road to success, we mustn't let our ego's become a controlling factor in the way we act and make decisions. Also by Ryan, Trust Me I’m Lying – is an eye-opening insight into how the modern media operates, the economy that drives it and how the system can be manipulated.

Robert Greene was one of the most influential people in Ryan Holidays life and his book The 48 Laws of Power outlines key steps to understanding how to use and enforce your power.

A few other books that aim to help you live your best life are A Guide to the Good Life by William Irvine and Meditations by Marcus Aurelius.

Guidelines is my eBook that summarises the main lessons from 33 of the best-selling self-help books in one place. It is the ultimate book summary; Available as a 80-page ebook and 115-minute audio book. Guidelines lists 31 rules (or guidelines) that you should follow to improve your productivity, become a better leader, do better in business, improve your health, succeed in life and become a happier person.

Action Steps

  • Use journaling as a tool to reflect on how you handle obstacles. Acknowledge if you let them consume you or if you start looking for an opportunity. Note down what happened and how you can improve next time.
  • Use obstacles that you have faced and overcome as a way to help others, whether it be people going through similar situations or someone facing a difficult scenario. Help them see the opportunities that can arise from the obstacle.
  • Consider any obstacle that you may face and the different perspectives you can take on it. Remember, there is always more than one way to look at things.
  • Purchase the full book from Amazon.




This summary is not intended as a replacement for the original book and all quotes are credited to the above mentioned author and publisher.