A Powerful 2000 Year Old Life Hack & Creating Work That Lasts for Generations with Ryan Holiday

In this episode we discuss how our perception of reality dramatically shifts what actions we take, why you should embrace 2000+ years of wisdom to be happier and more productive, how to stop judging yourself and others based on your achievements and root your identity in something within your control, we look at how we can cultivate a more humble and resilient world view, discuss strategies for connecting with top tier mentors, and much more with Ryan Holiday.

Ryan Holiday is a media strategist and writer. He is the bestselling author of over five books including The Obstacle is the Way, Ego is The Enemy, and most recently his upcoming book Perennial Seller: The Art of Making and Marketing Work That Lasts. Ryan previously worked as the director of marketing for American Apparel, working on several controversial campaigns, before starting his own creative agency. His work has been featured in The Huffington Post, Fast Company, Forbes, and more!

Why you should understand the Stoic discipline of "perception"
The way in which we see the world changes how we interact with it
How to accept situations as they are, not as you want them to be
Why you shouldn't waste time figuring out how things happened, who is to blame, etc - you should shift your focus to constructively determining the next thing to do
“There’s no problem so bad (in space) that you can’t make it worse”
The challenge of perception is not making the situations in your life worse with interpretations, resentments, anxieties
The story of Amelia Earhart and how you can use it to take action in the face of challenges
When you’re offended, when you think something is beneath you, you are projecting onto that situation something that may not be there
How do you react when people don’t think you have what it takes?
How to make yourself the most important person in a room, not by posturing, but by what you can contribute
How we can flip obstacles on their heads and view setbacks as opportunities
“What stands in the way becomes the way”
We have the ability with our minds to change how anything means
Setbacks make some people worse, some people tough it out, other people get even better
What is “Stoic Optimism” and why stoicism is not a focus on the negative
The distinction between Being and Doing and why its so critical
Should you do the “right thing” even if it pisses people off, hurts your chances of being promoted, causes political infighting, and worse?
Many people make the choice unknowingly between being and doing - and end up one day wondering where it all went wrong
How do we untangle success from our identities?
How do we avoid the trap of judging people based on their achievements?
The importance of being able to measure yourself by an internal score card - and not the external score card of accomplishment and achievement
Focus on basing your identity on an internals scorecard that is within your control
Decide what’s important to you, and root it within the things you control
How do we anchor our identity and self worth on a more stable footing?
How to have a more humble and resilient worldview
The critical difference between stoicism vs pessimism and how to look at both sides of the coin and realizing there are no good or bad outcomes - just outcomes
Everything is relative and subjective - someone in the third world would kill to live the life you may think of as failure
The world isn’t saying “this is happening to you because its bad” its just saying “this is happening”
The hard work of stoicism is the practice of doing it every day
“The message is the marketing” and how you shouldn’t distinguish between the making and the marketing when creating something
Why Ryan writes so much about ancient philosophy and how you should focus on rooting your ideas in timeless principles
The tactics Ryan used to build a relationship with and become an apprentice of Robert Greene
The people who need mentoring the most often get the least mentoring
Do well and a mentor will find you, put in the work, show the potential, and then mentors will naturally start to show up in your life
How Ryan approaches the creative process and the strategy he uses to test new ideas
You have an idea, you test that idea, and you work on it every single day - it gets 1% better every day - and at the end it’s finally good
Every book should be an article before its a book, every article should be a dinner conversation before its an article
Most of the marketing of anything that lasts is really about the product itself
Strategies Ryan recommends for finding a market for our ideas or concepts
Don’t create a solution in search of a problem, find problems and build solutions
How to uncover the problems that people are struggling with that you can help solve
What are needs that people have that there are currently no solutions?
How Ryan would start building an audience from scratch today if he had to start over
If you don’t collect your fans and have direct access to them - you are at risk - own your relationships with your customers and fans as much as possible
How Ryan deals with staying creative and productive with a new born child
Why Ryan hates the question of “what's the biggest struggle you’ve had to overcome”
Time you spend dwelling on the past (negatively or positively) is wasted time and attention
What Ryan journals about every morning and how he implmenents stoic philopsphy into his life
And much more!

Thank you so much for listening!

Please SUBSCRIBE and LEAVE US A REVIEW on iTunes! (Click here for instructions on how to do that).

This Episode of The Science of Success is brought to you by our partners, That Moment Podcast. That Moment explores the pivot that changes everything: moments that open doors for discovery and growth, but also bring the looming possibility of failure. Each show features different leaders and innovators sharing their stories of taking risks in business and in life. That Moment is produced by Pivotal, who believes when change is the only constant, people and businesses must be built to adapt. Get the details of their first episode "It Was Essentially Disrupting Ourselves" here and check them out on iTunes, Google Play, and Soundcloud.

SHOW NOTES, LINKS, & RESEARCH

[Book] Perennial Seller: The Art of Making and Marketing Work that Lasts by Ryan Holiday
[Book] Ego Is the Enemy by Ryan Holiday
[Website] Ryan Holiday
[Book] Meditations by Marcus Aurelius
[Book] Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram
[Book] The Tao of Seneca: Practical Letters from a Stoic Master, Volume 1 Seneca presented by Tim Ferriss Audio

Episode Transcript

[00:00:06.4] ANNOUNCER: Welcome to The Science of Success with your host, Matt Bodnar.

[0:00:12.6] MB: Welcome to The Science of Success. I’m your host, Matt Bodnar. I’m an entrepreneur and investor in Nashville, Tennessee and I’m obsessed with the mindset of success and the psychology of performance. I’ve read hundreds of books, conducted countless hours of research and study and I am going to take you on a journey into the human mind and what makes peak performers tick with the focus on always having our discussion rooted in psychological research and scientific fact, not opinion.

In this episode we discussed how our perception of reality dramatically shifts what actions we take, why you should embrace 2000+ years of wisdom to be happier and more productive, how to stop judging yourself and others based on your achievements and root your identity and something within your control. We look at how to cultivate a more humble and resilient worldview, discuss strategies for cultivating top-tier mentors and much more with Ryan Holliday. 

The Science of Success continues to grow with, now, more than a million downloads, listeners in over a hundred countries, hitting number one New and Note with Noteworthy and more. I get listener comments and emails all the time ask me, “Matt, how do you organize and remember all these incredible information?” A lot of her listeners are curious how I keep track of all the incredible knowledge I get from reading hundreds of books, interviewing amazing experts, listening to awesome podcasts and more. 

Because of that, we’ve created an epic resource just for you; a detailed guide called How to Organize and Remember Everything, and you can get it completely for free by texting the word “smarter” to the number 44222. Again, it's a guide we created called How to Organize and Remember Everything. All you have to do to get it is to visit successpodcast.com and join our email list or text the word “smarter” to the number 44222. Again, that “smarter” to the number 44222. 

In previous episode we discussed the dangers of playing it safe in life. How we can learn to celebrate more; the power cheering on, showing up, and serving other people. How to balance the acceptance of negative emotions with amplifying the good and focusing on the positive. What it means to live life in the front row. Lessons learned about living life from people who are fighting for the lives and much more with our guest John Vroman. If you want to live a life full of joy and celebration, listen to that episode. 

Lastly, if you want to get all the incredible information in this episode, links, transcripts, everything were going to talk about and much more, be sure to check out our show notes. Just go to successpodcast.com, hit the show notes button at the top. 

[0:02:49.6] MB: Today, we have another awesome guest on the show, Ryan Holliday. Ryan is a media strategist and writer. He’s the best-selling author of over five books including The Obstacles is the Way, Ego is the Enemy, and most recently his upcoming book, Perennial Seller: The Art of Making and Marketing Work That Lasts. 

Ryan previously work as the director of marketing for American Apparel working on several controversial campaigns before starting his own creative agency. His work has been featured in the Huffington Post, Fast Company, Forbes, and more. 

Ryan, welcome to the Science of Success. 

[0:03:22.2] RH: Thanks for having me. 

[0:03:23.1] MB: We’re very excited to have you on here today. I’d love to start out with one my absolute favorite topics from Obstacles is the Way was the concept of perception and kind of the idea of perceiving things as they are as opposed to as we want them to be. Could you kind of explain that concept and touch on that a little bit? 

[0:03:43.5] RH: Yeah. The Obstacles is the Way is book I’ve tried to root in ancient philosophy known as stoicism, and that the Stoics talk a lot about — They have thing, the discipline of perception. What they're really talking about is the way in which we see the world changes how we interact with it. Not The Secret. Not, :”Hey, if I wish for this, it will come true,” but if you think that something is unfair, it will be unfair and it will feel negative. If you think that something simply is what it is, it will be easier to deal with. 

What the Stoics are trying to do is see everything objective and they're trying to remember that there really is no good or bad, or positive or negative in any situation, it's just what we tell ourselves about it. I think, “Look, an entrepreneur doesn’t have time to think about whether something is right or not, or fair or not, or appropriate or not. Just has time to think about what we’re going to do, because we have payroll to meet, we have employees that we’ve got to handle. We’ve got goals that we’re trying to achieve.” Getting distracted about whether we wanted this to happen or not is really just a poor use of resources. 

I think on top of that, it’s trying to then see the good in every situation. What is the opportunity that this presents for me? What am I going to with this situation? If there’s some difficulty or trauma or problem, obviously, you’re going to say, “I’m going to reluctantly deal with this,” or you can say, “Oh, this gives me this chance to do this thing I wasn't going to do otherwise.” 

[0:05:26.3] MB: I think this discipline really opened my eyes. Once you’re kind of aware of this idea, it's so common to see people who are kind of trapped in a cycle of getting caught up in non-acceptance of the way things are and they’re so caught up in, “OH, this isn’t fair.” “Oh, this shouldn't be this way.” “Oh, I shouldn't have to deal with this,” and that really causes a lot of sabotage when they’re trying to achieve whatever goals that they’ve hey set out. 

[0:05:51.4] RH: Yeah, of course. Not only that, I think people waste a lot of time trying to figure out how stuff happened. They want to know who’s to blame. They want to know how this could have been avoided. They’re not looking at it constructively in terms of preventing it in the future. They’re just dwelling on how they got to this point rather than spending time thinking about how they're going to get to the next point. 

I think it obviously bears worth pointing out, there is a quote from Chris Hadfield, he’s the Canadian astronaut. He’s saying, “There's no problem so bad in space that you can't make it worse.” I think part of what the discipline of perception is not making it worse with interpretations, or resentments, or worries, or anxieties. It's just dealing with the thing in front of you because that's hard enough as it is. 

[0:06:46.1] MB: That's a great quote, and we actually have an upcoming interview with Chris. Listeners, definitely have a lookout for that. Got a fascinating story. I think that quote is really important and really underscores why it's so critical to perceive things as they are as supposed kind of as you want them to be. 

[0:07:03.9] RH: Yeah, exactly. They are what they are. Let's make the most of them. Let's not spend a second wishing they were otherwise is what the Stoics would say. 

[0:07:15.5] MB: Is that the chapter where you kind of give the example of Amelia Earhart. I thought that was a really powerful story from the book. 

[0:07:22.8] RH: Actually, I use that story, the discipline of action, which is, “Okay, it's not just how you see the information, but what do you do with it?” Amelia Earhart was famously early in her career offered a spot on a flight that was to be the first female transatlantic flight, except for she wasn't — It basically all for show. She wasn't going to fly the plane. There’s going to be two male pilots who were doing the flying. She was basically going to be the navigator, which meant she was just going to sort of sit in the back. In some senses is a very patronizing offer. It’s an offensive offer. the other two pilots are paid. I believe she wasn’t paid. 

You can picture her getting that phone call and you could picture her being perfectly within her rights to slam the phone down and say, “How dare you? I deserve better,” and she did deserve better. That's not what she did. She said, “Yes,” she took the flight. She used the fame that this sort of token opportunity brought with it to build a platform to build a name for herself which she then used to do what she wanted to do. 

Then part of this too is when you're offended by something, when you think that something is beneath you, this is also a form of judgment. This isn't taking something for what it is and working with it to the best of your ability. This is projecting on to it, sort of a deliberate animus which might not be there. It might just be that the system is inherently fair or that the system is indifferent to you as a person, and then saying, “Okay, all I need to do is get my foot in the door. I need to work with this. I’m going to make the most of it,” and I think that's what she did. Had she not done that, where might her career have gone? 

[0:09:12.5] MB: I share that story a lot with people who are just getting started. It reminds me of another tactic you recommend in ego, which is the idea of the canvas strategy. Can you talk a little about that? 

[0:09:25.3] RH: Yeah. Early on in my career, I think any young person — Bing a young white guy, obviously the discrimination or the adversity that I faced sort of have been nothing compared to a woman trying to be a pilot in the 1920s. Any young person can at least superficially relate to being underestimated, to being seen as unnecessary, to being seen as less than. In any point in your career, particularly early, there are going to be people who don't think you have what it takes, and what are you going to do with that? Are you going to overcompensate for it by being confident overconfident, overconfident and make things worse? Are you going to say, “Okay, look. I’m consider to be the least important person in this room. I’m going to work with that and I’m going to make myself an important person in this room not by my posturing, but in terms of what I can contribute.” 

I think if you're an intern out there, an assistant out there, really embracing the idea of, “Look, my job is to make my boss look very good, and I’m going to make myself indispensable in this organization not by chasing credit, but by making everyone in this room better and finding opportunities for other —“ I said canvas. Finding canvases for other people to paint on.” Is that finding articles for your boss to read? Is that staying late and doing extra research on this project that you know they haven’t had time to look at? Is it giving ideas away to other people inside the company that they can take credit for? Is it bringing them potential clients or projects or opportunities or introducing them to new things that you as a young person might have insight into that an older person might not? What are the things that nobody else in the organization wants to do that you are willing to do? Sort of building up your credibility and your skills that way not by trying to get credit, but in some ways, by deliberately giving credit away. 

[0:11:24.6] MB: I think there's a corollary to that as well when you think about taking responsibility for something. So often people think, “Oh, I need to deflect the blame. I need to make sure that I don't get caught up in this.” When in reality, counterintuitively, often taking responsibility, taking the blame for when things go wrong is really one of the most powerful things that you can do. 

[0:11:45.0] RH: Yeah, I would think that's true also. Look, earlier on in your career, it's accepting that your role is to deal with and take the heat for stuff that other people don't want to have to do, that that's part of the job. If you can embrace that, if you can do the things that other people don't want to do, then all of a sudden people are going to start to lean on you. They’re going to send you stuff. They’re going to start to see what you have. Nobody is going to hand you the position you magically want. I think you have to earn it. 

[0:12:17.3] MB: Another on the topic from Obstacle what I’ve found really interesting. In many ways, it’s kind of the core thesis of the book. Talk a little bit about how should we approach dealing with setbacks. 

[0:12:28.5] RH: I think this goes to the discipline of perception a little bit as well. Obviously, are you going to see this as this thing to put up with? Are you going to see this as this thing that’s very unfortunate? Are you going to see this as a setback, or are you instead going to see it as an opportunity of one kind or another? Marcus Aurelius, who’s probably the most famous of the Stoics, he has this line, he says, “The impediment to action advances action. What stands in the way becomes the way.” 

What he really means is that everything that happened, whether it’s a person being rude to you or a flight that's been delayed or a piece of legislation that failed to pass. This is negative in the sense that it's not what you wanted to happen, but it’s positive if you decide that it then provides an opportunity for you to do something, whether that's teach someone something, whether that's even just practicing forgiveness or acceptance. Everything that happens, we had the ability with our minds to change what that means to us. 

Andy Grove, who was the CEO of Intel for many years, he would say, “Bad companies are destroyed by crisis. Good companies survive them, and great companies are improved by them.” That’s sort of the stoic mindset, is that setbacks make some people worse, some people tough it out, and then other people go, “Oh, this is actually great, because now I can do X, Y, or Z.” That's the sort of stoic optimism that I really find inspiring. It's not saying, “Oh, hey! Everything’s awesome,” but it’s saying, “Hey, this presents to me an opportunity to do something that might be awesome, that had things gone my original way, I would've been able to do.” 

[0:14:21.0] MB: Tell me little about in ego, you talked about the distinction between being and doing.

[0:14:27.4] RH: Yeah. We’re really talking about the difference between appearance and reality, or sort of posturing and being the real deal. There's a speech that John Boyd, he was a great fighter pilot, and then sort of a groomer in the talent in the Pentagon for many years. He would give the speech to young up and comers. He would say, “You’re going to come to a fork in the road, and the fork in the road is — ” He would say, “it’s to be or to do.” 

Look, you can be someone who chases rank, he was saying. You could be someone who sucks up to your superior officers. You could be the kind of person that rubber stamps the right projects or tells people what they want to hear, or you could be someone who dedicates himself to the truth to a larger cause, just serving your country in a way that might not be rewarded by rank but it's the right thing to do. 

Boyd’s career was an example of this. I would guess 98% of people listening to this have never heard who he is, but he’s arguably the most important strategist in the Armed Forces in the latter 20th-century. He shepherd through the F-15 and the F-16. He was instrumental in the strategy of the First Gulf War. He’s now taught on all these different war colleges. What he was looking at doing is the right thing. He didn’t care about piss people off. He didn’t care if he killed people’s pet projects. He didn't care if he didn't get promoted. What he cared about was the work, was doing good work. 

I think we all have fork in our own careers that is similar to that. Are you going to be the person who pretends to be an internet millionaire and sells this bogus lifestyle? Are you going to be someone who actually builds something that matters? Are you going to chase being a bestseller, or are you going to chase writing books that have real impact? Are going to chase some meaningless job on Wall Street or are you going to try to make a difference in people's lives? What are you going to do? 

That choice, I think a lot of people make unknowingly. They’re not conscious of that fork, so they just gravitate towards what pays better, what seems to get the most recognition, and then they end up one day wondering where all the time went and why they haven't done anything important. It’s just something that I think everyone needs to be aware of, is what path are you on in life? Are you the person who is being important or you’re doing important things? I think that's the question. 

[0:17:13.3] MB: In many ways that distinction reminded me of the distinction between the fixed mindset and the growth mindset that Carol Dweck talks about, and kind of the idea that if you're sort of in a fixed mindset world that’s all about proving and demonstrating how awesome you are, but when you're sort of in a growth mindset place, in many ways, you're focused on getting better, improving kind of concrete development and growth. 

[0:17:35.0] RH: I guess they’re similar. I don’t know — To me, what Carol Dweck is talking about is the difference between sort of being smart and working hard. If you think you're smart become someone said you're smart, I guess that's one thing. If you think that you work really hard in you’re learning and you’re getting better, one of those attitudes might look better on the surface, but the other attitude — It’s like the other attitude, over time, is going to bear greater fruit. Yeah, you got to decide which of those people you’re going to be. Are you going to chase sort of superficial recognition or are you chase doing real work? 

[0:18:14.0] MB: That makes me think a little bit as well about another concept, I think you call it humbleness in Ego, but it’s the idea of how do we untangle success from our own kind of identity and how do we not fall into the trap of judging people based on their achievements.

[0:18:14.0] RH: Yeah. Look, I think one of the most insidious parts of culture is thinking that the things that we've done say something about us a person good or bad. If you think that the fact that you can afford a nice car says that you’re successful and important, you’re going to feel great when you have that nice car, but if that car gets repossessed, you have to sell it because you’re investing in your company or something. Now, all of a sudden, you don't feel the same way, but you’re the same personal. The only thing that changed is what car you drive. 

If you think that you're doing awesome because your company is doing awesome, what happens when the market shifts, or what happens if Google decides that it's going come into your market and replace you? The realities that the world can sort of turn on a dime. The best laid plans, as we know, can turn to nothing very quickly. 

These things don't change us. The difference between first class and coach on an airline other than price is nothing. They’re just chairs on an airplane, and so you want to be able to measure yourself not by this sort of external scorecard of accomplishment of recognition or achievement. You want to be able to measure yourself based on what went into them, because that’s really the only part of that equation that you control. 

I wrote this new book. I think it’s great. I think it’s one of my best books, but I could die before it comes out or there could be a natural disaster the week out and it could get no recognition, or Malcolm Gladwell could write a book with the same title and no one would care about my book. There are all these things that could happen that before it came out, when it was still in my control, I was quite proud of it and I knew that I did a good job, but then if I let these sort of external metrics decide whether it was good or not, I’ve now taken my confidence and my happiness and my identity and put them out to other people's hands and that sets us up to be disappointed, it sets us up to feel less than. It’s just not a great position to be in. 

[0:20:58.8] MB: How do we anchor our identities and our self-worth on that more stable footing? 

[0:21:04.5] RH: I mean you’ve got to decide what's important to you. Ideally, you want to root it in the things that you control. Again, you take a book — Actually. Obstacle is the Way was a good example. When The Obstacle is the Way came out, it did okay. It’s sold all right, but it was nowhere near what it's become in the subsequent few years. 

If I only felt good about it selling a certain number of copies I would have found that the book was a failure for quite some time. Really, the book hasn't changed. The book is the same book from when I finished it a year before came out to the day it came out, to flash-forward years later and its sold hundreds of thousand copies. Nothing has changed. I haven't changed the words, and the page haven't changed. Those are really what I should be focused on then, what you want your sense of good or bad or positive or negative to be rooted in is the part that you control. I control the amount of work that went into it. I controlled the ideas within it. I controlled the amount of time I made for it. I controlled those things. What I don’t control is what critics say. I don't ultimately control how many copies it’s sold or how much money it makes or this important person or that important person liked it. 

You almost have to be — The stoics would say you’re in different those things. Not that you don’t want them, but it’s nice to have them but you fine if they went away too, but that’s not easy to do. I wasn't exactly happy that the book didn't hit the bestseller list the week it came out or in the weeks’ sense I would've liked for that's to have happened, but that it didn't happen was okay because I was able to root my judgment of the book in the fact that I knew that it was the best thing that I was capable of that that time. 

[0:23:09.0] MB: In Ego you also talked about the idea of entitlement. Tell me a little bit about that. 

[0:23:14.2] RH: I don’t know what you mean specifically, but I think related to what we’re just talking about is a lot of people think they're entitled to the parts of the labor that aren't there. They think that they’re entitled to everyone liking them or everyone telling them that they’re awesome. They're entitled to being in control of the universe, other people's opinions. It's like you see this with very egotistical people. You could even see this with Trump. It’s like he doesn't get that people are allowed to not like him. It’s so deeply bothers him and he’s so used to being in control of everything that he ends up wasting incredible amounts of time and energy and actually ends up making things worse for himself trying to control these things that are inherently outside of his control. 

I think part of ego is just believing that the universe is revolving around you and that it responds to your wants and needs. I think a more humble but more resilient approaches is realizing that, look, you’re a tiny fleck in this universe and that it’s on you to make it what you want it to be within your sort of limitations as a human being. I think this is true as a creative too. Again, get you are entitled to the work. You’re not entitled to what comes to anything past that. You’re not entitled to any results. That's where you are, at the at the mercy of these larger forces. That’s inherently humbling. 

[0:24:50.8] MB: In a world where change is one of the only constants, people and businesses must be adaptable. This episode of the Science of Success is sponsored by our partners at That Moment, a new podcast about the pivot that changes everything. 

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[0:25:49.4] MB: Do you think that there's — You touched earlier on the idea of stoic optimism. After I kind of read Obstacle, and I’m naturally sort of a very pessimistic person. I always think about all of the things that can go wrong and the ways that it can get wrong. Do you think there's a danger within stoicism of getting too focused on the negative?

[0:26:09.9] RH: The stoics don’t believe in a negative. They’re saying they want to look at all possibilities, but that all the possibilities are the same. That neither there’s no good possibilities and there's no bad possibilities. There's just potential outcomes in a given situation 

I think, look, there’s pessimism. Pessimism is always looking at what could go wrong and then despairing because it can go wrong. Stoic is instead saying, “Look, I'm going to launch this company and it could be successful. It also could fail and I could lose all the money that I put into it, but that’s not going to stop me from trying. I still think that my odds are better of success than failure, so I’m going to push through and I’m going to put everything that I can towards doing so. If it does start to look like it’s going to fail, here are all the things that I can do to prevent that. Here’s all the options that I have since I’ve thought about it in advance that I can try to plan for those contingencies. 

I think there's pessimistic people and I think those people are not happy and there's anxiety and worry in that pessimism. That's not what stoicism is supposed to be about. Stoicism is thinking about the worst case scenario so it doesn't catch you by surprise. Also, so you can plan for it or plan around it or prevent it. The optimism in stoicism is that it proceeds anyway. It proceeds despite the odds or despite the dangers or risks and it goes into them not blindly but with one's eyes wide open. 

[0:28:03.7] MB: I think that's a great point. The idea that there's not good or bad outcomes, there are only outcomes, and we need to think — 

[0:28:10.9] RH: Yeah. The stoics would say there is no good or bad. There's only perception. There's just how we see things. Think about it. Look, what you would see is a bad outcome, somebody else might see as heaven on earth. You failing at a business to someone in the third world, they would kill just to get where you think failure is. These things are all relative and subjective and we should remind ourselves of that. If we can strip that comparison out of the equation, we can see that there are just outcomes, period. Some are probably more desirable than others and some probably present more options than others. At the end of the day, when your company fails, whether you believe in God or whether you believe in some chance or fate, the world isn’t saying, “This is happening to you because it's bad.” It's just happening. It just is an event. When a tree falls or when a person dies or when you get a year older, these are just facts of the universe. They're not good or bad. It's human beings who try to put them in categories and then feel stressed and unhappy because of those categories. 

[0:29:35.0] MB: Where do you think people go wrong when they try to concretely implement stoicism into their lives? 

[0:29:41.9] RH: I say in the book, all these is very simple, but that doesn’t mean that it’s easy. Look, I can say what I just said and 20 minutes from now someone could call me a name and objectively that name is just a word. There's no difference between this word or that word. It doesn't change who you are and it doesn't mean that it's true or not, but that's simple. It’s pretty straightforward. It’s logical, but that in the moment when someone calls you an asshole, that doesn't — You want to react. 

I think the hard work with stoicism is the practice of it, not just the practice, like doing it, but can you practice it? Can this be something that you get a little bit better at every day? I'd like to think that I am, but stuff still bothers me. It's always going to bother me, but hopefully it bothers me a little bit less every day. 

[0:30:44.1] MB: I’d love to kind of transition now in talking about your new book, The Perennial Seller. One of the core ideas from the book is the notion that you shouldn't distinguish between the making of something in the marketing of it. Tell me about that. 

[0:30:58.9] RH: I think a lot of people creatively — and I know this sounds very different than what sort of the important topics we’re just talking about, but I’ve tried to write books that are going to stand the test of time. I’ve tried to write books that whether or not they appear on the bestseller list are going to sell well every single week. I want to create things that last, that help people that work regardless of trends or current events. Part of the reason that a lot of creative work doesn't do that is that people go off in a cave and they make things and then they try to figure out after how to make. Somebody decides, “I want to have a podcast, “and then they make a podcast and then they go, “How do I get listeners for this podcast?” They don't think about it as —They think about it as separate problems rather than the same problem and that in a weird way getting the audience, sort of getting the attention for it matters as much, if not more than how you made it, because if you can't have one, the effort that went into the other was somewhat poorly spent. 

[0:32:12.5] MB: I think that makes a ton of sense, and you have a couple of examples from the books Shawshank Redemption, 48 Laws of Power. Would you share one of those stories? 

[0:32:22.3] RH: Yeah. Look, Robert Greene who wrote the 48 Laws of Power, he was my mentor. I was his research assistant for a number of years. Look, that book could've been — That book was written in the mid-90s. That book could have been rooted in current events. It could have talked about the Clintons. It could have talked about no television shows that were on at that time. It could've talk about all of these things, but instead Robert wrote a very timeless book about power. He wrote a book about power that wasn't designed for your typical business executive. It was very pragmatic and ruthless and he says that it's A-moral, meaning that it's not judging good or bad about the strategies. The result was he’s created this timeless book that’s unlike anything else in the field. Its closest equivalent is probably Machiavelli's, The Prince, just written 500 years before. 

In a way, he’s done very little marketing for the book because the book is the marketing. When people read, it so refreshingly provocative and bold that you got to read this book. The book is the marketing in many ways and it's also designed to be timeless. Again, even though it’s 20 years old, it doesn't feel dated. He could've written it yesterday, he could have written it 20 years from. It would still be the same value. 

Part of the reason I rooted my books in ancient philosophy is that I know that I’ve thought about the things that I’ve thought for a decade or two decades. I know that ancient philosophy has worked for thousands of years. What am I going to bet on? Something that occurred to me when I was 25, or am I going to bet on something that somebody else came up with 2500 years ago? Rotting your work in timeless principles is really really important. 

[0:34:26.6] MB: You were pretty young when Robert Greene, I guess, when he became your mentor, right? 

[0:34:32.1] RH: Yeah, I was 19 or 20. 

[0:34:34.9] MB: How did you develop that relationship or how did he become your mentor at such a young age? 

[0:34:41.3] RH: I think become is the operative word there. There wasn't like this day where I was anointed. It wasn't like some ceremony or swearing-in. I worked for someone who works on his website and then Robert and I started talking. I started working on his projects. I had read all his books. We met for lunch one time. He told me that he was looking for a research assistant. I volunteered. He gave me a trial project and then I did good on that and he gave me another project. Then over five or six years, I proved myself. I did good work. It was an organic growing process. There was never — I think some people go, “I need to find a mentor,” and that’s not really how it works. What you need his mentoring, and that can come from lots of different sources and people and it usually evolves slowly. 

I think the other part is when you begin to show potential or talent — If you're totally clueless and you don’t know anything and you have no marketable skills of any kind, you're not going to find a mentor. In some ways, it's inherently unfair, the people who need mentoring the most get it the least, but that's how it works. 

Sheryl Sandberg, she says it’s not find a mentor and you will do well. Do well and a mentor will find you. That's how it happens. You’ve got to put in the work, show the potential and then people will be willing to invest in you. 

[0:36:17.5] MB: Back to Perennial Seller, tell me a little bit about how do you approach the creative process? 

[0:36:24.5] RH: I think about the audience a lot about. I think about who am I making this for. I think about what is this project going to do. What am I trying to accomplish? What is success look like on this project? It's a hell of a lot of work too. When I sold Perennial Seller in early 2015, I thought it would take a few months. Here, it is coming out in late 2017. Took over two years, and not like two years of sporadic work, but two years of almost every day making it a little bit better. 

I think people think that books or movies or whatever, these sort of flashes of inspiration or flurries of activity. Really, it’s you have an idea and you test that idea. You start to think that there's some promise to it, and then he does work on it every single day and it gets .01% better each time you touch it and these improvements compound and at the end, probably much later than you think, it's eventually finished and you have it. 

[0:37:39.7] MB: How do you go about testing your ideas? 

[0:37:42.6] RH: I say every article should be — Every book should be an article before it's a book. Every article should be a dinner conversation before it’s an article. I think you’ve got to interact with people who are least representative of your audience and see is there a potential? Is there a flash or a glint of intrigue in their eyes when they hear it? If there's not, then you got to keep tweaking the idea until you get there. 

[0:38:13.0] MB: Give me a specific example. How did the Perennial Seller, for example, evolved from a dinner conversation into an article into eventually a book? 

[0:38:24.4] RH: Yeah, it’s funny. My editor came to my wedding and she was like, “Hey, you should do a book on book marketing.” I thought that was interesting, and I explored it. I wrote a book proposal and sold. There was some interest, obviously, or they wouldn't have bought it. Then I started talking to people about a book and I found — Most of the people I know are not authors, so the idea of a book about book marketing, it kept falling flat. Then I realized too that a lot of the strategies that I was going talk about would be out of date very soon, and so I pivoted towards, generally, how do you make anything that lasts or how do you market anything that lasts. 

Then most of that marketing actually has to do with what the product is itself, so then it was really hard to make and market anything that last. Obviously, I had to sit down and write it and there are heir different sections that I talk to people about, but it evolved from this suggestion about one topic to being a full-fledged book of — I don’t know, 50,000 or 60,000 words, maybe more, about a totally different thing. That wouldn't have happened — If I just written the book — Let's say I had known that my publisher would publish anything that I wrote, so I would have thrown together a first draft about book marketing, and then it would have been published and it would've been much worse and it would’ve had much less chance of success that I not had this conversation. I thought I not got pushed back from the people that I did talk to it about. 

[0:40:10.5] MB: For somebody who’s listening, how would you recommend that they think about finding a market or an audience for their ideas or for that sort of concept that they have around creating something? 

[0:40:25.0] MB: I would think what are problems that people have that need solutions? I think that far too much creative work is a solution in search of a problem, when really it's got to be the other way around. What’s a problem that people have? The Obstacle is the Way is a book about philosophy, because that’s what I'm interested in, but it’s actually a book about how to overcome obstacles, because that's what other people are interested in to come together. 

You have to find a problem to solve, and the deeper and more perennial problem and the better your solution, the more likely you are to create something that's going to endure and that's going to be, hopefully, financially lucrative as well. 

[0:41:13.8] RH: How do you approach digging in and really discovering kind of what those problems are or finding people that kind of unearthing what the challenges they have that you could maybe help talk to or address? 

[0:41:28.5] RH: To me it’s kind of obvious. What are problems you have in your own life that other people share? What are problems the people in your life seem to talk about? What are the things that you wish you'd known when you were younger? What’s the thing that you went through that you had to white knuckle, that you wish that there had been solutions for? What are the things that you're experiencing in your life? You're not pulling up a phone book and trying to call people and go, “What are some problems that you have?” but you're looking for resistance and difficulty that other people have accepted or have caught up with that there might be a solution to. What did people sang before there was the song Happy Birthday? What people read before what to expect when you're expecting? Where did people go to when they would get hung over in the weekends and before there was a brunch spots? What are needs that people have to which there are currently no solutions? Then your work is presented as an alternative to the status quo. 

[0:42:39.3] MB: If you were to have to kind of start from scratch today, if you had no existing audience, no relationships. How would you go about building an audience or building a platform for yourself? 

[0:42:51.9] RH: Look, I remember when I did that. It's not like that — I wasn't gifted this platform. I remember in 2008 or 2009 I wanted to be an author and I knew I would write a book someday, but I didn’t have any way to tell people about it. I started an email lists where recommended books to people thinking that one day I might be able to recommend one of my own books. That list started with 50 people that are mostly friends, and I sent the email out last night about Perennial Seller to 81 — Almost 82,000 people. I already did that list, so when other people started reading lists, I don't think it’s a good idea. I think that’s competition and I sort of already own that space, but I would think about what is a skill that I have? What’s something that I know about I could help people with? What's the most interesting thing about me that people don't know about that I could lean into? I’d go from there. It wasn’t like 30 years ago I started from scratch. It was not that long ago. I still think I’m very much in the in the beginning stages of doing the things that we’re talking about. 

[0:44:09.7] MB: In the book, you talk about the importance of building a platform. Can you explain that concept a little bit more? 

[0:44:17.3] RH: Look, what we’re just talking about with the list. I could have built a blog, but I built an email list instead, and that email list is now 80,000 people, that when I have a book, I email. The email is probably this single best medium for selling books right now. 

If you don't collect your fans and organize them and have direct access to them, like you, with your podcast, if you were only dependent on iTunes to get access to your fans and iTunes suddenly decided to charge, or iTunes mysteriously shut down, or people started hating iTunes. These would all be really bad problems. If you’re an Uber driver, you're dependent on Uber for your living. You don't have a platform. Uber has the platform, and that's why they're worth billions of dollars. You want to own your relationship with your customers, your fans, as much as possible. 

[0:45:09.3] MB: Has having children impacted your productivity at all? What have been some of the challenges you’ve had to overcome in terms of staying on track with how much you create and market with having kids? 

[0:45:22.5] RH: I only have one son and he’s less than nine months old. The vast majority of my creative work came before all these and it’s certainly a process that I'm adjusting to now. Look, you got to decide what you want your life to look. You got to decide what your priorities are, what's important to you, and you got to organize around that. I think one of the reasons that I was comfortable having a kid is that I’d gotten my life to a point where there was freedom to do that and that had been something that was always very important. I didn't want to have to show up at a job. I wanted to have to determine my own schedule. I wanted to be somewhat financially independent as a result of some of my success. I changed tell how I spent money, how I invested money. That this change what I said yes to, what I said no to. It certainly changes your priority. There's a few hours that I spend in the morning now that before I get started that weren’t there before, but I think the rewards are more than worth it. 

[0:46:30.0] MB: What’s one of the hardest struggles that you’ve personally had to overcome? 

[0:46:36.7] RH: I kind of hate that question, because, one, I think it implies — One; i don't like this idea of this sort of the adversity Olympics. Who has gone through this, and was gone through that, and let's all compare them? I think the other part of it is that it implies that it's like this thing we do ones that determines who we are. 

To me, the struggle is waking up every day and being tired and you’d go to work or not. There’s this fire to put out or that that fire to put out, or this employee has this problem and how are you going to deal with it? To me, the struggle is this sort of day-to-day thing that I focus on. At the end of the day, I don’t think about it anymore. I don't think about —2014, I wrote about Ego. It was a very hard year for me. I went through a lot of stuff, but I also don't think about it at all. Part of the reason I wrote it is so I don't have to think about it again. Part of the stoic optimism is also realizing the time you spent dwelling on the past either negatively or positively. Patting yourself on the back for getting through something is really just wasted time is not being directed at what you’re going to do next. That's where I prefer to focus my energy. 

[0:47:55.6] MB: I think that’s a great point and a very insightful look at how to think about not only where we focus our attention, but why it's kind of irrelevant to think about just what’s the hardest struggle that you’ve had overcome. I think that’s really interesting perspective and philosophy. 

[0:48:15.1] RH: Thank you. 

[0:48:15.7] MB: For somebody who's listening to this episode that maybe wants to start or concretely implement some of the ideas we’ve talked about today, what would kind of be one action or activity you’d give them as a starting point to do that? 

[0:48:29.2] RH: Obviously, I wrote the books to be a starting point and I see them very much as a starting point. The point of stoic philosophy is not that it’s this thing that you read ones and then you know forever and you’re this magical wizard. It's something you read and you do. I journal about it daily. I write about it. I think about it. I read about it. I have conversations about it. 

The books, for me, are part of that process. Writing them was me spending an incredible amount of time with some of these ideas. I would start with reading, and you don't have to read my books. You could read Marcus Aurelius, or Seneca. Tim Ferris just put out a free collection of Seneca’s letters that i think are great. You could check out that. Listen to podcast about it. I would just start by immersing yourself in this information because there’s a lot of it out there. It’s done by people who are smarter than you, they’re smarter than me. These are people, some of the wisest people who ever lived, and I take advantage of it. 

[0:49:31.3] MB: I would echo that as well. I think that one of the most interesting things about your work, and you touched on this earlier, is that these ideas are timeless. They’ve been around for, literally, thousands of years and there's a reason, it's because they’re such effective strategies for dealing with, as you put it, sort of the everyday struggle of getting up, dealing with setbacks, achieving things in a world that is often very difficult. 

[0:49:56.8] RH: Yeah. I would agree with that. 

[0:49:58.2] MB: Where can people find you and your books online? 

[0:50:02.1] RH: My websites is ryanholiday.net. You could sign up for the reading list we talked about there. All my books are on Amazon. Yeah, I think I’m at Ryan Holiday on pretty much every social media platform. 

[0:50:13.7] MB: Awesome. Ryan, thank you so much for coming on here sharing all of your wisdom, ton of great insights about stoicism and creativity. 

[0:50:22.5] RH: Thank you for having me. This is really cool. 

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