The Obstacle is the Way

Book notes for “The Obstacle is the Way”, The Ancient Art of Turning Adversity to Advantage by Ryan Holiday

Quick review:

A quick read covering stoic thinking and how it can be applied to one’s life. Lots of examples and repetition, but that did not bother me as this tends to be necessary to really get people to internalise the lessons from this sort of book. Sure, it could be condensed to 50 pithy quotes, but reading those quotes would not have the same effect as reading this book. The ideas feel familiar, in a good way, and appeal to me. I am sure that applying them would make me a better and more effective person. I will definitely read some Meditations and Senneca after this, and try and apply many of the highlighted ideas

Questions raised:

To get more detail on these ideas, go to the source, and read Meditations and Letters from a Stoic (Senneca) next. There are many interesting ideas in the book that it would be good to get more angles on, so as to really burn them into my brain (or reject).

Insights, lessons learnt:

  • read more about stoicism
  • try and perceive your life from the outside when unsure of how to resolve an issue
  • be persistent and you can resolve huge issues
  • see the opportunity in every obstacle
  • don’t let fear hold you back
  • etc.!



What blocks us is clear. - Systemic: decaying institutions, rising unemployment, skyrocketing costs of education, and technological disruption. - Individual: too short, too old, too scared, too poor, too stressed, no access, no backers, no confidence. How skilled we are at cataloging what holds us back! location 138

It’s not just: How can I think this is not so bad? No, it is how to will yourself to see that this must be good—an opportunity to gain a new foothold, move forward, or go in a better direction. Not “be positive” but learn to be ceaselessly creative and opportunistic. Not: This is not so bad. But: I can make this good. location 191

Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest. location 228

This insight lives on today in Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.” Rockefeller, like all great investors, could resist impulse in favor of cold, hard common sense. location 291

through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles. There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means. location 384

Don’t forget, there are always people out there looking to get you. They want to intimidate you. Rattle you. Pressure you into making a decision before you’ve gotten all the facts. They want you thinking and acting on their terms, not yours. So the question is, are you going to let them? location 416

So go ahead, feel it. Just don’t lie to yourself by conflating emoting about a problem and dealing with it. Because they are as different as sleeping and waking. location 480

Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this? And the answer—like it is for astronauts, for soldiers, for doctors, and for so many other professionals—must be: No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive. location 498

Objectivity means removing “you”—the subjective part—from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective. location 536

Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do? How much more quickly and dispassionately could you size up the scenario and its options? location 541

Having learned early in life that reality was falsely hemmed in by rules and compromises that people had been taught as children, Jobs had a much more aggressive idea of what was or wasn’t possible. location 711

So many people in our lives have preached the need to be realistic or conservative or worse—to not rock the boat. This is an enormous disadvantage when it comes to trying big things. Because though our doubts (and self-doubts) feel real, they have very little bearing on what is and isn’t possible. location 721

This is radically different from how we’ve been taught to act. Be realistic, we’re told. Listen to feedback. Play well with others. Compromise. Well, what if the “other” party is wrong? What if conventional wisdom is too conservative? It’s this all-too-common impulse to complain, defer, and then give up that holds us back. An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. location 747

Socrates had a mean, nagging wife; he always said that being married to her was good practice for philosophy. location 805


While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life loom very large. location 963

If we’re to overcome our obstacles, this is the message to broadcast—internally and externally. We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile. location 1003

Thickheaded and resistant to change, these are the types who are too self-absorbed to realize that the world doesn’t have time to plead, argue, and convince them of their errors. Soft bodied and hardheaded, they have too much armor and ego to fail well. It’s time you understand that the world is telling you something with each and every failure and action. location 1104

The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture. location 1179

Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires. location 1203

An artist is given many different canvases and commissions in their lifetime, and what matters is that they treat each one as a priority. Whether it’s the most glamorous or highest paying is irrelevant. Each project matters, and the only degrading part is giving less than one is capable of giving. location 1206

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods. location 1257

What setbacks in our lives could resist that elegant, fluid, and powerful mastery? To be physically and mentally loose takes no talent. That’s just recklessness. (We want right action, not action period.) To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap. But physical looseness combined with mental restraint? That is powerful. It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening—like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals. Because we are. location 1455

You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is—at best—indifferent to your existence. location 1672


A CEO calls her staff into the conference room on the eve of the launch of a major new initiative. They file in and take their seats around the table. She calls the meeting to attention and begins: “I have bad news. The project has failed spectacularly. Tell me what went wrong?” What?! But we haven’t even launched yet… That’s the point. The CEO is forcing an exercise in hind-sight—in advance. She is using a technique designed by psychologist Gary Klein known as a premortem. location 1691

premeditatio malorum (premeditation of evils). A writer like Seneca would begin by reviewing or rehearsing his plans, say, to take a trip. And then he would go over, in his head (or in writing), the things that could go wrong or prevent it from happening: a storm could arise, the captain could fall ill, the ship could be attacked by pirates. location 1709

Not: I’m okay with this. Not: I think I feel good about this. But: I feel great about it. Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it. location 1874

Sometimes when we are personally stuck with some intractable or impossible problem, one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people? Take it for granted, for a second, that there is nothing else in it for us, nothing we can do for ourselves. How can we use this situation to benefit others? How can we salvage some good out of this? If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation. location 1995

You can always remember that a decade earlier, a century earlier, a millennium earlier, someone just like you stood right where you are and felt very similar things, struggling with the very same thoughts. They had no idea that you would exist, but you know that they did. And a century from now, someone will be in your exact same position, once more. 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.