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Meditations by Marcus Aurelius

Andrew: You know how as entrepreneurs we keep facing obstacles? Lack of money, a developer we work with suddenly quits, our idea doesn’t work out, we’re too short, or in my case, very handsome, all these obstacles just get in our way constantly. Well that’s what this session is about. It’s about how to turn your trials into triumphs.And to lead us we’ve got Ryan Holiday, he is the founder of Brass Check Marketing. And the session is going to be based on his book which is called, “The Obstacle Is the Way.” We pulled out some key ideas from the book which we’ll be talking about throughout the session. Ryan, thanks for leading us.Ryan: Yes, it’s good to be back.Andrew: I want to understand the problem and as tough as it is for me to be too handsome…

Ryan: Sure.

Andrew:…or some of those other challenges that I brought up earlier, the British had an even bigger challenge. And in the form of the Germans’ use of a new form of warfare in World War II. What was that?

Ryan: The story I tell in the book is this idea of – well I talk about it in two ways. We talk about the Blitzkrieg and then are you talking about specifically the North African desert?

Andrew: Yes, the Blitzkrieg was huge.

Ryan: Sorry, you cut out for a second. Can you hear me?

Andrew: I was talking about the Blitzkrieg, lightning war.

Ryan: Yes, sure. So what happens in World War II is that the Nazis unveil this tragedy known as the Blitzkrieg, which is essentially this lightning attack by using mostly tank and other mobile, sort of, forms of warfare, that is designed to catch the enemy not only off guard but sort of overwhelm it with speed and force in a very short amount of time. And it’s designed to sort of create a break in the enemy’s lines that forces them to scramble.

And what I talk about is shortly after the invasion of Normandy Eisenhower, he’s lead up to this point what is the largest amphibious invasion in military history. But slow going allows the Germans to wage this counter offensive. It’s 200,000 men. It’s 13 divisions. They’re threatening to essentially throw the allies back into the sea, which is the worst place you would want to be if you’re trying to retreat.

Basically the entirety of World War II rests in this moment, and there’s this magnificent scene. Eisenhower, he assembles all the generals into a conference room in Malta and he says to them, “The present situation is to be seen as one of opportunity for us and not disaster.” He says, “There will be only smiling faces at this conference table.”

And the reason he says that is for the first time an allied general sees the fatal flaw inside the Blitzkrieg, which is that it’s basically putting all your eggs in one basket, right? By charging ahead, not worrying about your flanks or your supplies, you are charging head first into a net. And Eisenhower realized that if the allied troops bent instead of breaking, if they sort of allowed this and they circled around it, they would capture something like 50,000 Germans in this net. Patton, he says, “It’s like they’ve just stuck their head in a meat grinder.”

And so up until this point the Blitzkrieg had been undeniably effective. It worked time and time again because the enemies always saw it as being overwhelming, as being intimidating, and they broke. They broke discipline. But what Eisenhower was able to do was see it not just objectively, but almost optimistically. He built a strategy in response to it that created what was known as the Battle of the Bulge, which was ultimately one of the most decisive allied victories in World War II.

And so for me this is a metaphor, right, because in our own lives we face these obstacles. It looks like a competitor is about to move into our space, they’re way bigger than us. Someone comes charging at us. Our first instinct is to get out of the way, to dodge it, to assume we’re more or less fucked, right? But it’s not. And if you can hold your ground and see objectively what is in front of you, you can often find the weakness inherent in that position of strength. And that’s what Eisenhower did if that answers your question.

Andrew: Okay. It does answer my question. And I was kidding earlier when I said too handsome. Because frankly, design has always been a challenge for me here on Mixergy, and I hired a stylist to help get me dressed. And I found someone, finally, to help me with the design of the interview, the layout here, of our conversation. But, I find that I have modern day problems.

And as I was looking at your book and going over what we’re going to be talking about today, I see historical references to Rockefeller. References to big stars like George Clooney are coming up. How does their challenges relate to my every day problem of someone else about to start an interview program that has more money than me, has a big studio? Or someone who’s listening in my audience who has a challenge who can’t afford to pay their developer what they’re worth, and their developer’s working part time and they can’t get as much work out of them as they need?

Ryan: Sure, it’s interesting. So I based this book on an exercise or the thoughts of Marcus Aurelius, the Roman emperor. And I think you read this book, you read what are essentially the private thoughts of the most powerful man in the world, written in about 170 A.D. And what you are struck by is how relevant the thoughts of this man writing 2,000 years ago are to the problems that we face.

And there was actually one passage that he writes in there where he’s talking about the problems faced during the reign of the emperor Trajan, who came well before Marcus Aurelius, and how similar the problems that Trajan faced were to the problems that Marcus Aurelius faces. You extrapolate that out, the problems that you and I face, the problem that President Obama is facing right now, are more or less the same timeless human problems: not having enough money, not having enough time, being stressed, being over worked, being over-burdened, facing bankruptcy, facing conflict, facing heartache, facing loss.

We all face these more or less same problems. Yes, the manifestation of them changes. For them it’s a shortage of gold coins. For you it’s a shortage of access to a line of credit. Whatever it is, right? The details change but more or less we are human beings who are dealing with the same problems that we have always dealt with.

Andrew: I see.

Ryan: And so I wanted to focus on sort of objective historical problems where there was not much controversy and there was not much argument. So if you’re sitting there telling me that you’re having a problem with your developer, I’m going to tell you what you can do about it. And then you’re going to go, “Oh, no. But my problem is different because it’s this. And then I’m not going to be able to do that.”

I wanted to sort of pick things where there’s no argument. Like what Eisenhower did and it happened, it’s done, it’s clear and it’s inspiring because I would much rather deal with a developer problem than 13 Panzer divisions, right?

Andrew: Right.

Ryan: And so the point is what can we learn from history? What I say about practical philosophy is that, you know, in the last 5,000 years chances are someone faced more or less the same problem that you’re facing right now. And they got over it, it didn’t kill them. And they probably wrote about it. So let’s find what that is and at least incorporate that into our solution, not to say we have to do the exact same thing, but we can certainly learn from it.

Andrew: So you’re going after timeless ideas as opposed to tactics that will only work today and be out of date tomorrow?

Ryan: Yes, exactly.

Andrew: Okay. All right. Why don’t we start with them then? Here’s the first one and this is really a timeless idea: control your emotions. There was a time where I mentioned this guy a moment ago. Let’s bring him up on the screen. This is John D. Rockefeller. We think of him as being one of the most successful entrepreneurs of all time, but he was around in 1857. What happened in 1857?

Ryan: Yes, so 1857, shortly before 1857, Rockefeller gets his first job. He’s 16 years old. He’s a sort of aspiring financier. He’s a bookkeeper. He wants to be an investor, right?

Andrew: Okay. And his first job is an assistant bookkeeper.

Ryan: Yes, he’s making 50 cents a day, right?

Andrew: Okay.

Ryan: And the panic of 1857 strikes. It’s a crippling national depression, probably one of the worst that America has ever faced. It actually originates in Ohio where Rockefeller is based. It’s pretty much the worst thing that can happen to a kid who just got his first job in finance. But Rockefeller, he later said, “I was inclined to see the opportunity in every disaster.” And that’s what he did. He actually used this moment in time, this financial panic as his sort of college education in the market.

So he sits down. He watches what everyone else is doing; he sees the mistakes that seasoned investors are making. Because he basically has no money in the market, he’s able to be objective about it. He’s able to see how disastrous emotional reactions can be to market fluctuations, the problems that it causes. And then crisis after crisis in his life he’s able to apply these lessons because of instead of freaking out, instead of quitting or running away and getting another job, he was able to see this all objectively. So the first part of the book to me is about controlling those perceptions, controlling those emotions so we can both understand and learn from whatever situations we find ourselves in.

Andrew: Okay. Was there a time in your life where you felt like you’re disaster striking, and you wanted to lose control, wanted to lose your emotions?

Ryan: Sure. All the time. It’s funny, you know, I talk about one of my favorite examples of controlling your emotions. I talk about sort of space training, right? As they train the first set of astronauts, it wasn’t so much their ability to fly aircraft that qualified them for, you know, the Apollo missions. It was their ability to regulate and control their emotions.

Andrew: Yes.

Ryan: To not hear a bunch of alerts and then start hitting random buttons and blow themselves up. That’s basically the main skill they were looking for in these astronauts. And so I really liked that, and I was thinking about all the problems that I’ve made worse in my own life. You know, someone sends me a nasty email. I want to respond, I want to get angry, I want to tackle, you know, a superior about it. I want to fight back against them.

When really what I realized early on when I was working at a large company, I was the Director of Marketing at American Apparel, I realized that there would be these emails that I would get. And if they would make me so upset, and then I thought for a second, “What if I never saw this email?” Like, what if I accidentally deleted it or I didn’t read it? How much different my life would be, right? The conversation would resolve itself or sputter out.

And I wouldn’t be upset and I wouldn’t be angry, right? I would just not know that this potential trigger had been pulled. And it’s what got me thinking, I can just have that reaction and not respond. I don’t have to read it and freak out. I can read it and not do anything about it. And it’s funny I read that stuff about NASA and I included it in the book. And a few weeks ago, Chris Hatfield, the astronaut, he did a [???]. And he was joking that in space there’s no problem that a human can’t make worse.

And I think that that’s what you want to think about with your emotions which is okay, something happened. It’s an objective event outside you. Can you not make it worse with an overreaction? Can you not make it worse with your emotions, either being upset, being hurt, being surprised, you know, being resentful? Can you not make it worse with your emotions? Like, the other cliche is the first rule of holes is to stop digging. Well, that’s the first thing our emotions do usually, is dig us into a deeper mess than we were already in.

Andrew: Okay. All right. First idea we talked about is controlling your emotions. Not allowing them to get away from us. Let’s go to the next one which is to use the obstacle against itself. You give the example of how this man did it. Let me bring up Gandhi. What was the obstacle that he came across?

Ryan: Well, it’s interesting. You have Gandhi who was, you know, an educated, incredibly smart man. But he had essentially no resources, right? And there he is. He’s facing the imperial British Army, the most successful largest army on earth, right? And he somehow manages not only to defeat them, but they defeat themselves because of the position that he put himself into. So I think what a lot of times we do we find ourselves over-matched in a particular position or a particular conflict; we try to imitate the people that we are competing with or that we are challenging. We try to do what they do.

And it’s very problematic to come at people in their own strength. So what Gandhi did was not challenge the British militarily, he challenged them politically and ethically. And he used essentially the size and the strengths of the British Army against himself. He challenged them and put them in positions where they would have to use force against a significantly weaker enemy that caused them to lose the moral high ground. What he would do continually, whether it was the march to the sea.

Andrew: Why did he do the march to the sea?

Ryan: Salt March.

Andrew: Here, that’s what we’re looking at, right? I pulled it…

Ryan: Sure.

Andrew:…from this site. The Salt March. Why did he do the Salt March?

Ryan: So basically what Gandhi did was that he identified a completely bankrupt part of British policy which was essentially the tax on salt, right? His argument was put many people in poverty, prevented people from being self-sufficient and made them dependent on the colonial British.

Andrew: Mm-hmm.

Ryan: So he said look, we’re going to march to the sea. We’re just going to collect our own salt. It wasn’t actually a replacement. It was a symbolic gesture. We’re going to march to the ocean, and we’re going to collect salt in flagrant violation of this policy. We’re going to force them to enforce it. The optics of that policy are going to be displayed for the entire world to see. We’re going to incite them essentially to embarrass themselves.

Andrew: Okay.

Ryan: He didn’t say look, we’ve got to raise an army and then we’re going to fight the British in a pitched battle because they would lose. Instead we are going to do something where we look particularly harmless. Where what we are doing is something that people empathize with or sympathize with or basically find no fault in, and we’re going to force them. We’re [??] force their [??] force them to do something that will be indefensible. That’s what he did. He would do that over and over again.

It’s the same playbook that Martin Luther King later executed, which was to sort of lean into the strengths of your enemy. Their…in many cases that’s their numerical and forced superiority, forced them to exercise that in an indefensible and justifiable way and use the media and public perception against that…against that enemy until they eventually have to either change the policy or relent entirely.

Andrew: Okay. So instead of trying to combat them by being exactly like them, which is what most people would try to do, you want to use their power against them. In Gandhi’s case — in the example that you just gave — I think Lord Edward Irwin was the viceroy of India. He had basically two options: one was to go in there and stop them from marching, and the other was to just let it go and hope it peters out and hope it quiets down.

He decided, you know what, if I attack them then it’ll look bad. Like you said, the optics are just not going to be helpful. On the other hand, he said he’d let them go and let them do it. What happened was this big march kept getting bigger and bigger and made a huge statement that backfired on Irwin.

Ryan: Right. Essentially it puts them in what strategists call the horns of a dilemma. You have to pick which one you want to get impaled by…

Andres: See.

Ryan: …and neither of them is pleasant.

Andrew: Okay. There’s good advice right there. Let’s go on to the next big point which is to reverse your perspective. I mentioned earlier that we were going to talk about this man [pause]. This is George Clooney. You use him as an example.

Ryan: Mm-hmm.

Andrew: He was…I didn’t realize that there was a point in his life where he was bitter. I feel like look at how good looking he is and he…

Ryan: Sure.

Andrew: …always was. So what is…

Ryan: Sure.

Andrew: …so what does he have to be bitter about?

Ryan: Did you know George Clooney almost played professional baseball as well?

Andrew: No. I didn’t know that.

Ryan: Yeah. I learned that recently. Basically the story that I tell is one from early on in his career. Like all actors who are just getting started you go out and you go on auditions. Right? And you are usually not successful. I think it’s something we’ve all experienced the equivalent of. We go for job interviews and we feel intimidated. We feel embarrassed. We feel self-conscious. We want to be chosen very desperately. It’s a human emotion in that you go into the room and you basically want to beg for this person to accept you, to tell you that you’re awesome…

Andrew: Yes.

Ryan: …to choose you for the position.

What that forgets of course –and it’s something that you realize when you hire someone for the first time — is that despite all your positions of power and influence, you desperately need to fill this position. When a casting director is casting for a role in a movie, it’s not as if they can’t…they won’t fill the role. They’re like hey, you know what, we’re not going to have a leading man in this movie. By definition they are paid to find someone to fill the spot.

What Clooney realized…Clooney sort of understood that flip and he said to himself okay look, they have a problem. I’m the solution to that problem. So instead of going and groveling or coming at it from a position of weakness, I’m going to understand and empathize where they’re coming from, and I’m going to position myself as the solution to that problem.

What a casting director is looking for is yes, someone who looks good; yes, someone who can do the lines. They are looking for someone who’s going to show up on time every day, who’s going to be dependable, who’s going to be affordable. They’re looking for the perfect person for that role. They need you as much as you need them. That’s what Clooney thought about.

That flip I think is really important about any situation you’re in. What I realized early on in my career as well is that you go around, and you don’t want to get fired. You would never want to get fired from your job. So you endure all these seemingly negative situations because you don’t want to get fired.

But if you thought about it the other way, if you thought about it the other way. If you thought about – so let’s say you do something, you screw up. Now you’re on the edge of getting fired. That would feel like some massive personal failing on your part. You’re a loser, whatever. But if the day before you quit in indignation because you didn’t like your boss, it would be fine, right? You would’ve just left. If quitting a job is empowering, getting fired is not. But objectively they are the same thing.

Andrew: You’re saying in the end you end up in the same place?

Ryan: Right. You don’t work there anymore. That’s all that it means. And so what the stoics talk about is this idea of eliminating the explanation and interpretation of events and seeing them objectively. And you basically flipping your perspective allows you to see those things objectively because you’re understanding that one event can have two very different explanations, and therefore, you logically go, “Okay. They’re all manufactured. They’re not inherent, right?”

And to me that’s something I try to think about in my own life. What is the explanation that I’m bringing to this situation that’s making it either really bad or really intimidating? And what’s a different explanation that I could try that would give me the perspective and the ability to see through the baggage I’m bringing to the table?

Andrew: Here’s one guy who I noticed did that. Oren Klaff is a guy I interviewed a while back on Mixergy.

Ryan: Okay.

Andrew: And he said he did this. He used to walk into investor meetings feeling like he had to beg them for money or be a jester who was going to entertain them so that they would give him money. And he said once he changed his perspective, he just reversed it by thinking, “Well, these people need a good entrepreneur to invest money in. These people need someone who they can bank on, literally.”

Ryan: Right.

Andrew: Then he started to prize himself, and they started to feel like they had to work to get him. And that was a small change in perspective that allowed him to start raising money and it was hugely impactful.

Ryan: Yes.

Andrew: That’s what you’re talking about.

Ryan: Yes, there’s another story I tell about in the book. I don’t tell in the book but it’s something that stuck with me: Ulysses S. Grant, his sort of first experience in battle. He’s hunting this enemy and he’s afraid, he’s afraid. He desperately does not want to meet the enemy in the field of battle because he’s never been in battle. He’s worried what it’s going to be like. And finally, they come to the enemy’s camp, and he realizes that the enemy ran away, that they weren’t there. They hastily made camp and escaped.

And then he realized in that moment that the enemy was just as afraid of him as he was of them. And that’s sort of the whole point. That’s the importance of empathy, the ability to see the same situation from somebody else’s perspective, and understand that it’s not all about you. And often the story you’re telling yourself, even though it’s egotistical in its own way, it’s actually holding you back. It’s actually making your own life more difficult.

Andrew: Let’s go to the big board for the next big idea which is to focus your efforts on what you can control. Who is this guy?

Ryan: Is it Tommy John?

Andrew: Yes.

Ryan: There we go.

Andrew: What happened with him?

Ryan: Yes. Before I tell the story I think it’s very indicative that one of the first things they tell addicts in the 12 Step groups, the first thing they sort of go over is distinction between what we can change and what we cannot change. And the reason is people waste an immense amount of energy, an immense amount of discipline and willpower on trying to change things that are outside of their control. Like, you have crappy parents, they treat you bad. You can wish really hard that you had different parents, but you don’t. These are the parents that you have.

And the part that you can change is how you interact with them. Whether you interact with them. Whether it hurts your feelings. Whether you carry and hold the resentment. Those are the things you can control. And what the stoics did and the stoics repeatedly stress, and I talk about it in the book, is this distinction between the things that are up to us and the things that are not up to us.

And I tell the story of Tommy John because Tommy John is one of the longest playing pitchers in major league baseball. There were these moments in his career that other people would have considered to be either hopeless situations or impossible situations, but he really broke down, you know, is this something that I can change? So he blows out his arm, his pitching arm, and the first doctor tells him, like, “Look, your career is over. A pitcher can’t function without this ligament in his arm.”

And he talks to another doctor who has an experimental idea where they basically take the ligament from his non-pitching elbow and put it into his pitching elbow. This surgery becomes known as, “Tommy John” surgery. The doctor tells Tommy there’s a one in 100 chance that if he gets the surgery he’ll be able to pitch again. And so Tommy goes, “Oh. So you’re saying there’s a chance. Well, I’ll do it.” And he rehabilitates… He gets the surgery, he rehabilitates, and he begins pitching again.

Ironically, he actually becomes a better pitcher after the surgery than he was before. But the point was, getting in the surgery was something he controlled. There was a chance that if he got it, he would improve. It wasn’t an impossible situation, it felt that way, but it wasn’t.

The other story I tell from Tommy is he’s, I believe, 40 years old, and he was cut from the New York Yankees because they said he was too old. They’re almost cutting him out of pity. They’re like, “Look, you’re too old. You don’t want to play baseball anymore.” And he says, “Look, if I show up in training camp….” He says, “If I show up, am I going to get an honest look? Are you actually going to look at me?” And they said, “You shouldn’t be playing baseball. You should quit.” And he said, “Look, do I have a chance of making the team again if I show up and make a good… If I test well at camp?”

And they said, “Yes. Fine. There’s like a one in 100 chance again.” And he says, “Fine, I’m there,” and he trains for months and months and months. He ultimately ends up starting for the Yankees that year, opening day. Because it was something that was in his control. Right? If they said, like, “Look, you’re never going to play again, you’re banned from baseball,” he would have moved on and did something else.

But what he did was, he would focus intensely on these situations where he had a chance. It didn’t matter if he had a sliver of a chance, a tiny chance, what mattered is, did he have a chance.

Andrew:: And he picked being able to play, not in his control, that’s up to them, showed up, completely in his control, so he shows up. That’s what you want us to take away.

Ryan: Right. The effort, the process, that’s what he controlled. The effort. And then whether it worked out or not was outside of his control, but the process was enough, and that’s the distinction that you need to make, and the place that you need to put your effort.

Andrew: All right. On to the big board. The next big idea is to not listen too closely to others, or even to our own doubts, and one of the examples you give is this man and the device that he is holding.

Ryan: Ah, okay. Yeah, you know, I talk about Steve Jobs, he had what… If you read the Walter Isaacson biography, in some ways it’s very critical, and it should be. Steve Jobs was not a perfect individual by any means. But he had what these people call the “Reality Distortion Field,” which, I get. I think they actually mean derisively. But it was this ability for him to see past the boundaries of what other people thought was and wasn’t possible. Right?

So he has an engineer come in, he wants this mouse built a certain way, and the engineer says, “Nope. I’m sorry, it can’t be done. It doesn’t work.” And Steve Jobs says, “Okay, you’re fired.” And then the next guy who comes in his job is to say the mouse is possible, and they work to make that thing happen.

So it sort of goes to what we were just talking about earlier, but I think the problem is we are told over and over again in our lives to be practical, to be realistic, to be reasonable, to listen to what other people are saying. And the problem is, a lot of what other people say or bring to the table has to do with their own baggage, it has to do with their personal beliefs about what is and isn’t physically possible.

That is arbitrary, and Steve Jobs sort of saw through that, and he was notorious for setting these very ambitious goals and deadlines, knowing that is was far better to sort of overreach and try to make something that was perfect, that was flawless. It was beyond whatever capacity people thought that they were capable of. Because that’s better than, you know, trying to be reasonable and then failing at that. Trying to be realistic and failing at that.

And, you know, I think we all have doubts in our lives about whether we can pull something off, but I know, in my experience, I’ve yet to find a series of commitments that I’ve made that I didn’t ultimately end up fulfilling in one way or another. And I am better off for having to have made those aggressive commitments, and then needing to grow and expand to reach them, then I am when I am curbing what I think I am capable of.

I think you see this… Like we were talking about running earlier, before we started the call. You think that your capacity is X, but, objectively, your capacity, your physical capacity, is usually larger than whatever your mind tells you you’re capable of, or vice versa. And if you push past those, that’s when you really test yourself and you find your ability to grow. And so, I think, part of doing great things is having those ambitious goals that force you to reach beyond, maybe, whatever you would be inclined to do if there wasn’t a gun to your head. Like, I find if I sign a contract for a book I’m going to deliver that book, right?

If I’m just, you know, fooling around at my desk, am I going to deliver that book? And am I going to deliver it at that date that I’ve committed to do, that I’m now legally obligated to meet? And so I think deadlines, commitments are super important, and I think the more we can get them to lead us, to be in front of us a little bit, maybe sprint ahead of what we think is possible, the more we’re going to accomplish.

Andrew: I found that myself with running specifically where if I signed up for a marathon, I felt forced to go out and train and to run. And I’ve always completed them one way or the other, even if it meant I had to walk. Like the Vegas marathon I did…

Ryan: Sure.

Andrew:…where I walked it. Seven and a half hours it took me to finish. They stopped doing water support in Vegas. They put the water bottles along the route on the floor for anyone else who wanted them, and I just had to deal with it. But, yeah, you’re right.

Ryan: Yes.

Andrew: All right. Onto the next big idea which is to take action and make your own fortune. And you bring up this guy. How do you pronounce his name? Let me bring him up on the screen for you.

Ryan: Demosthenes. Can you hear me?

Andrew: Yes.

Ryan: Yes, Demosthenes.

Andrew: Yes.

Ryan: The Athenian orator.

Andrew: Okay.

Ryan: So Demosthenes. It’s a fascinating story. It comes from Plutarch, the Roman assayist. But basically Demosthenes he’s born into a wealthy family, but he’s physically disabled. He’s weak and frail. He has a speech impediment. And then I think he’s five or six years old and his parents die, which is terrible. So now he’s an orphan. His parents have died, and he’s basically given these legal guardians who plunder his estate. They steal all the money that he was meant to inherit. This is basically you’re a nine year old, this is like the worst series of events. You lose your parents, you lose your fortune, they neglect your education, you’re basically on your own.

So what Demosthenes decided he would do is he’d seen a great speaker and he was enthralled. And he wanted to become this person. And so his life’s task came mastering the art of oratory. And his other great cause was sort of taking revenge and earning back what had been stolen from him. So you sort of insert this almost movie montage-like series of events.

He decides he’s going to conquer his speech impediment by running and speaking while he’s running. So speaking while he’s out of breath. He practices shouting into the wind to develop his strength of voice. He conquers his speech impediment. He puts rocks in his mouth. And I’m not sure how this actually fixes it, but he puts these rocks in his mouth and he strengthens his tongue and his cheeks and his control over his speaking patterns, until eventually the stutter is gone, too. Then he shaves his head, half of his head.

So he’s too embarrassed to go outside, and he spends every day of the next several years working in an underground, like, I don’t know, war room that he builds for himself. And here he teaches himself the law, he practices speaking, he spends every waking moment of his life preparing for this destiny that he set for himself. Eventually he challenges the guardians in court. He wins in court. They contest it every step of the way. It’s a many year legal battle, but inch by inch he begins to win.

And he makes a name for himself as a speaker and as a lawyer. He eventually wins the case, but what he really won was this career, this calling. He becomes known as the “Voice of Athens.” He’s the greatest speaker in the city. He’s the most knowledgeable of the law. He wins back the fortune, but there’s nothing left. The fortune that he gets is he’s now this powerful and influential politician. You know, I think we all find ourselves in disadvantageous positions we’d rather not be in. Positions that are unfair, you know, given certain disabilities or problems or things we’d rather not have.

And it’s not simply, earlier we were talking about perception, it’s not simply a matter of, like, “Oh, I’m going to look at this as being the glass half full.” It’s not just about thinking that you want it to be better. It’s about taking those steps and actually making it better. About taking action, real action, sustained dedicated persistent actions against your problems and understanding that that’s where the real gains come from.

Andrew: Amazing. I like the idea of a guy who would shave half his head to force himself to feel like he couldn’t leave. To force himself to stay and work for two years until he made it.

Ryan: Right, right.

Andrew: Until he got where he needed to be.

Ryan: You know, I think, not to be flip about it, but today you get picked on, you get screwed over in your childhood. Like, the end of that story as we commonly see it is that the person goes on a murderous rampage.

Andrew: Right. As opposed to saying this is going to be something that can actually be useful. I’ve talked to multiple entrepreneurs who have gone into the basement, not by shaving their heads, not because they put some kind of penalty on themselves if they do, but they’ve said, “I’m going to go into the basement. I’m going to work quietly for a few years and build this thing out.” And ended up doing great.

Ryan: Yes.

Andrew: I see the power of that and it’s so much more useful than going on a murderous rampage.

Ryan: Yes.

Andrew: Not that those are the only two options. Onto the next point which is to start anywhere you can. You give the example of this woman. Let me bring up her photo up here. All right. There it is.

Ryan: Amelia Earhart.

Andrew: Yes, Amelia Earhart. What happened to her when she started?

Ryan: Yes, so, you know, it’s the 1920’s. She’s a female aviator. It’s a very different America; that is this is something that people eagerly embrace. And she finds the things that she is capable of doing are hemmed in by these various constraints and prejudices. And so she gets her, I forget what year, but she gets her first sort of offer that I think any reasonable person in her position would’ve found quite offensive. They’re looking to have the first female flight over the Atlantic, continuous flight over the Atlantic. And the proposition is this: she’s not actually allowed to fly the plane. There’s going to be two male chaperones. She doesn’t get paid, they do.

And basically they’re going to condescendingly treat her as though she is incapable of fending for herself. But someone has agreed to fund this flight and their first pick has dropped out, by the way. So does she want this leftover, declined opportunity that is less than ideal? Does she want to take it. And, of course, what does she say? She says, “Yes.” She says I’ll bite my tongue and I’ll say yes. She flies across the Atlantic. She becomes relatively famous for it and uses that as a launching pad for the rest of her, you know, famous flights, for the platform and the personality she builds.

You know, this was the chapter that I liked writing the most because it was the most personal for me. You know, I left college in 2007. So right during the financial crisis. My class, because I dropped out, my class graduated in 2008, 2009. So at the height of the economic recession from the crisis. And, you know, what I saw most of them do was the opposite of what Amelia Earhart did, right? They all moved back home with their parents. They waited, more or less unemployed, for the perfect job opportunity to come their way.

Meanwhile, you know, a handful of them, I would put myself in this boat, sort of took whatever they could, worked on whatever opportunities were there, and built something. And a bunch of them now ironically are just graduating from grad school, or they went back to school and got their PhD. And they’re still expecting some magical, perfect opportunity to fall in their lap. They’re waiting for Google to call them. They’re waiting for Microsoft to call them or Amazon to come offer and give them their dream job.

And what I want to tell them is, like, “Look, it’s never going to happen. That’s not how it works.” The perfect opportunity very rarely falls in your lap. In fact, a less than perfect, if not objectionable opportunity falls in your lap, you take it, you make the most of it. Then you make the most of 10 other seemingly inferior or frustrating opportunities and then you make your own way from there. And I just love that example from Amelia Earhart.

Andrew: What was it that you took that others would’ve felt like they were too good to take? What’s the opportunity?

Ryan: I dropped out of college for a job that paid me $30,000 a year.

Andrew: What was that?

Ryan: I was working in Hollywood. I took a job as an assistant, literally answering phones at a Hollywood management agency. I was willing to put up with an immense amount of shit because the person who offered me the job told me that I would get direct access from them and instruction from them. And that they would teach me and mold me into someone who could do more than answer the phones. And I was willing – you know?

Andrew: No, sorry. What were you going to say? I want to follow-up, but I want to give you a chance at first say.

Ryan: Yes. Answering someone else’s phone and scheduling their appointments is my worst nightmare. But I was willing to do it because I knew it would lead to something, and I knew that if I could get my foot in the door I would make it into something. And I could’ve waited until I graduated, but I knew that when I graduated I would be in the exact same position. I would just feel more entitled and be more impatient when it came to, you know, paying my dues so to speak.

Andrew: Right. What about then the idea that if you’re answering someone’s phone, if you’re taking the little jobs that people offer you when you have no other opportunities because there are challenges in front of you, that maybe the world starts to see you as a phone answerer…

Ryan: Sure.

Andrew:…instead of a marketer. They start to see you as a guy who goes and gets coffee instead of giving you the opportunities that people who they see with bigger potential.

Ryan: Sure. Two things about that because I think about it a lot. In fact, this guy, he told me. One of the best pieces of advice I ever got was he was, like, “You’re too bad of an assistant to stay as my assistant.” He wants a body to do this job that basically a monkey could do, but you have to illustrate some sort of promise or potential that makes you too good to be a lifer in that position. I quote Andrew Carnegie in the book. He says, “Ideally, your first job should introduce you to the broom.”

And he doesn’t mean you should be beaten with a broom, he means you should understand that you’ve got to start at the bottom. You’ve got to sweep the floors. You’ve got to learn the importance of sweeping the floors and ultimately decide that you want more for yourself. And so I talk about this with my own assistants and with my own employees, is be just good enough that you’re worth betting on. Not so good at the menial task that you’re irreplaceable at them.

Andrew: Okay.

Ryan: Because finding good assistants is very hard. And some people that’s the perfect job for them. Chances are you probably don’t want to be that person. And you don’t want to be the guy that gets coffee. You have to work twice as hard to show that even though I’m getting you coffee, I’ve got good ideas and you should listen to me. But if you’re sitting at home in the same bedroom that you grew up in, waiting for Larry and Sergey to call you and come be an engineer at Google, I think you’re going to be disappointed.

Andrew: Okay. All right. We have big visions for where our companies are going to go, but sometimes we just have to get that first customer really happy, giving them the little things that they’ll allow us to do.

Ryan: Sure. How many people listened to your first show?

Andrew: Ooh, you know what? No one.

Ryan: Right.

Andrew: I don’t think anyone listened. I can’t imagine there were more than ten, seriously.

Ryan: Right. I don’t think anyone read my first articles, you know? But I had to write them. You don’t get an audience because you want one. You get an audience because you’ve earned one.

Andrew: All right. I do remember William Quigley. I took a tape recorder into his office, and he was willing to have a conversation with me. And I recorded it and I don’t think I got ten people on there. It was very frustrating. All right.

Ryan: Is it still up on your site? Can people go back and listen to it?

Andrew: People can go back and listen to it, actually. Yes, it’s still on the site. I don’t even think William Quigley knows that he was my first interview. I was going to speak at an event and I said, “Can I come in and just do a pre-interview with you?” That’s the other thing: pre-interview. So I was going to do a pre-interview with him like my own assistant…

Ryan: Sure.

Andrew:… and record it and post it online. And he was okay with it.

Ryan: Wow.

Andrew: Onto the next and final point which is to have a mission bigger than yourself. I used to know this man as, oh here he is. Who’s this?

Ryan: Is that James Stockdale?

Andrew: Yes. I’ve been pulling articles off of Wikipedia. So it’s a little hard to tell who it is. And yes, it is James Stockdale.

Ryan: And you said what did you used to know him as?

Andrew: Wasn’t he the guy who was the – Ross Perot’s.

Ryan: He was.

Andrew: He was, right?

Ryan: Yes.

Andrew: Ross Perot’s running mate who came across looking like a bumpkin in the debates in the vice presidential debates. But he had this deep, rich history behind him that you talk about . . .

Ryan: Sure.

Andrew: . . . which was what happened to him during the war, in Vietnam.

Ryan: Yes, it’s interesting that we tend to know James Stockdale and John McCain for their political careers, you know, positively or negatively. But that really masks what was utterly incomprehensible heroism, bravery and strength that they showed during Vietnam. And again, whenever you think about the Vietnam war, James Stockdale, he’s shot down, he’s a fighter pilot. He’s a Navy commander. He’s flying a mission over Vietnam and he’s shot down.

And, you know, a lot of the people that I talk about in this book understood stoicism, but maybe not explicitly so. They didn’t actually study it. Stockdale had been given a copy of Epictetus, who is one of the great stoic philosophers. Literally as he’s parachuting down from the wreckage of his plane into what will certainly be a enemy capture, probably very strong interrogation, definitely torture, and possibly even death, he says to himself, “I am leaving the world of technology and entering the world of Epictetus.”

What he meant was my stoicism is going to come in handy in a North Vietnamese prison camp. Stockdale, as he’s parachuting down, he’s not thinking of himself. He’s thinking of the fact that as the highest ranking American POW, he will be in a position to lead the men who up until this point had been more or less leaderless in this camp.

He comes down, and he becomes this immense source of strength for the other men. He’s basically the leader that they needed. He used this all maybe in one of the worst things that you can imagine. He spends seven and a half years in this prison camp. He’s tortured. He’s beaten. He’s placed in solitary confinement. He uses this as an opportunity to provide moral support for the men that he is now responsible for.

Andrew: He is going through here. Look, this is a photo of him at the time. He is going through hell on earth. He says his mission will be to help other people instead of trying to deal with it himself.

Ryan: Yeah. At one point, and this is obviously an extreme example, he goes to kill himself. He attempts to kill himself not because he wanted the pain to end, but he wanted to send a message to his captors that he would not be broken and that they could not use him against the United States.

Actually, it’s funny. I just said the United States. The soldiers could actually speak to each other. They had this language of hand signals and movements. He would remind the other soldiers, he would say U.S. Not for U.S.A., or United States, but for unity over self. It was this idea of what we’re going through is hellish, and awful, and completely unacceptable by even the most liberal interpretation of the Geneva Convention. But we have each other and we have a responsibility to each other and to our country that’s going to allow us to endure this. We’re going to think about what other people are going through rather than our own problems and our own situations. That’s what’s going to give us the strength and fortitude persevere through this situation.

I mentioned John McCain earlier. John McCain was in the same prison camp. People don’t understand this or they don’t know this. John McCain’s father was a theater commander. He was an admiral also in the Vietnam War. When the North Vietnamese realized this, they offered to allow John McCain to leave the camp.

Normally the way it works is when you’re a POW, it’s sort of first one in, first one out. You would leave, you would get freedom exchanges over time based on your place. They realized that they have the commanding admiral’s son in captivity. They want to use this as a weapon. They want to embarrass the United States by inveighing or applying pressure on John McCain to get him to abandon his fellow prisoners and leave early.

John McCain, he actually refuses to do this. John McCain was tortured in a Vietnam prison camp, and that’s more than most of us will ever go through. But John McCain willingly endured that torture so someone else could leave first and so he would undermine the other men and women who were not as privileged as he was. To me, that’s just so incomprehensibly brave and stoic as to almost be without description.

Andrew: That’s the answer, then. When we’re going through trouble, instead of saying I only have to deal with this because I have to first heal myself, see if there are other people who we can help, or find a mission, any mission, bigger than our own current circumstances.

Ryan: Sure. Look, you’re an entrepreneur and you’re having trouble with the company. You’re stressed and you’re overwhelmed. You can think about how this affects you financially. You can think about all the problems that it’s causing for you, whether it’s stress in your marriage, or your life, or it’s just more than you signed for.

Or you can think about all the employees that you brought onto this business that are dependent on you for their livelihood or the customers who depend on your business to do what they do. Or in your case or in my case, our readers and fans who consume our work. It’s that ability to think of something a little bit larger than yourself that allows you to find something within yourself that maybe you didn’t know you had, and to give that little bit extra.

Andrew: The other thing I just recently found out as I was prepping for this session, is James Stockdale’s middle name is Bond. James Bond Stockdale.

Ryan: Really?

Andrew: Yea. It’s on Wikipedia so it’s got to be true. I’m zooming in a little too much.

Ryan: Of course.

Andrew: There it is. All right. The book is, “The Obstacle is the Way”. We covered a bunch of ideas from the book here in the session but obviously in a small session we can’t cover all. Follow-up, just grab it from anywhere. There it is. The Obstacle is the Way. Thank you so much for doing this session with me.

Ryan: Yea, of course. It was great.

Andrew: You bet. Thank you all for being a part of it. If you got anything of value, find a way to say thank you to Ryan. Ryan, what’s a good way for them to do that?

Ryan: You can just email me. It’s ryanholiday@gmail.com. It’s funny, you know, I did this for the growth hacking book and your readers really do email. It’s amazing. I’ve had some good conversations.

Andrew: You know what, you’re surprisingly easy to contact

Ryan: There’s worse things in the world than having people who like what you do email you and talk to you about it. And I think although obviously I’m very busy and have stuff going on, I think I’ve benefited from that relationship because it tells me what my readers and fans and my potential audience actually need, want and are struggling with. So that line of communication has been very beneficial and important to me.

Andrew: I tell people to do that all the time, not enough people take me up on that opportunity. I can’t tell you how many people I met that way. I’m about to, tomorrow, I’m going to go see Noah Kagan in a mansion in Napa that he rented for the week. He invited me to come by and say Hi, to hang out.

The only reason he and I connected was a few years ago I read his blog, I got something of value out of it and I sent him a note and as a result he and I became friends and we’ve known each other now for almost a decade.

Ryan: Yea, that’s how it works. We were talking about waiting for the perfect opportunity. No one is going to come force you and Noah to get to know each other. Very rarely is this unsolicited introduction going to flutter into your hands. You have to seize the offensive. In a very minor way, take some initiative, shoot someone an email and you never know what happens.

Andrew: You know I just realized actually, he thanked me. I commented on his site and he did something that no one had every done before, he sent me an email saying, “hey dude, saw the comment, thanks for writing on the site” which was unbelievable. So, of course then I stayed in touch with him and then I wrote a post or two on his site back then and we became friends.

Ryan: And you never know what people are going to go on to do. I think a lot of times people are very judgmental. They’re like, “This person’s a loser. I don’t know who they are. I don’t know what they’re doing”. You have a bunch of people that you emailed when they were just random people and then they went on to start this company, or do this thing.

Andrew: One great example is Mike Del Ponte. I got an email from Tim Ferris saying, “Hey, his stuff is really good. The Soma water pitcher that purifies water is beautiful, it’s really good, you might want to have him on.” I say, “yeah, let’s have him on.” I do a quick search and I realize, Mike emailed me back when he had a job working for someone who I interviewed. He said, “can you teach me this interviewing process, what do I do?” And I responded to him back then and he’s gone on to great things and one of those great things is building this company and he came on to do an interview about it. So yea I know what you mean.

Ryan: For sure.

Andrew: All right. Find a way to say, thank you. Really, don’t overwhelm people just find a way to say thank you. I’m going to do it right now. Ryan, thank you both for doing the session with me and my team said please don’t let Ryan go without saying thank you for helping us with Mixergy because you know so many great people that became interviewees here.

And I really appreciate the contribution that you’ve made to my personal mission here by introducing me to people who’ve come on to do interviews, courses and otherwise be a part of the community. Thank you.

Ryan: Awesome. It’s a pleasure.

Andrew: You bet. Thank you all for being a part of it. Bye guys.