0
SPEAKER_00
By the way, people who don t know, you are the director of marketing for American Apparel, correct?
0
SPEAKER_01
Yeah, it s a somewhat untraditional company, so it wasn t like a day where I magically got the title, but I was 21, 22 years old.
0
SPEAKER_00
Right, before I graduated from undergrad and college, where I ve literally accomplished nothing other than getting into college and not failing out, right?
0
SPEAKER_00
You had already had a position where most people probably wouldn t have gotten until maybe their late 30s or early 40s, generally, for something like that, is that right?
0
SPEAKER_01
Yeah, that s right, and look, you can tell yourself that story, and that leads to you thinking you re a lot better than you are, or you can tell yourself, I had to remind myself at the time, like, obviously it s great for my career to have this title, and I m gonna leverage everything I can out of it, but I also have to remember, like, this is not necessarily the equivalent position of being the director of marketing at Abercrombie & Fitch.
0
SPEAKER_01
Like, there are different companies on different levels, different circumstances, that being said, the stresses and the responsibilities
0
SPEAKER_01
and the temptations were all there, and the education was certainly there as well, but it was a whirlwind for Sherman.
0
SPEAKER_00
You mentioned earlier the idea that guys like Steven Pressfield, who ve sold a ton of books, might turn around and say, well, you know, I m no Jack Canfield, or whoever s name pops up.
0
SPEAKER_00
What if you have that, and you re not just keeping your ego in check, but for me, for example,
0
SPEAKER_00
I actually kind of have the opposite problem, not that I, well, my ego s so in check, it s a problem.
0
SPEAKER_00
That s not what I m saying.
0
SPEAKER_00
Self-conscious is actually more like it.
0
SPEAKER_00
Literally, I ll spend the entire Friday going through hundreds of emails, 90% of which are like, this show changed my life, I love this, I can t believe it s free, I wanna meet you sometime, and I m thinking, this is really cool.
0
SPEAKER_00
but I m not floating on top of the world like Jenny will say, cry me a river, you have 300 pieces of fan mail in your inbox, you should be on top of the world.
0
SPEAKER_00
I ll find myself saying either out loud or to myself, yeah, but look at Joe Rogan, his show is so huge, it s so impressive, we ve got this little piece of real estate and it s great for everyone, but man.
0
SPEAKER_00
Man, it s just so small, relatively speaking.
0
SPEAKER_00
And you start to beat yourself up.
0
SPEAKER_00
I find myself not in a weird spiral doing it, but it s almost like a bad habit where I m constantly finding that it s gone beyond serving a useful purpose, right?
0
SPEAKER_00
It used to be like, alright, I m hungry.
0
SPEAKER_00
I m gonna get to that level.
0
SPEAKER_00
This is inspiring.
0
SPEAKER_00
It shows me what s possible.
0
SPEAKER_00
I m really excited to be at that level someday.
0
SPEAKER_00
In the meantime, I m gonna enjoy the process.
0
SPEAKER_00
It s gone beyond that to, man, is this even possible?
0
SPEAKER_00
is what we have gonna eventually get there, and those moods change like the wind, but whenever I have that, it s not helpful, and it sucks.
0
SPEAKER_01
It s wasted energy is what it is, right?
0
SPEAKER_01
Because you re not focusing it on actually making yourself better.
0
SPEAKER_01
You re not focusing it on feeling good or fulfilled.
0
SPEAKER_01
It s just sort of pointless anxiety and compulsive thinking.
0
SPEAKER_01
So I think I go through that as well.
0
SPEAKER_01
I wrote a piece recently about envy.
0
SPEAKER_01
I experience envy and jealousy like every other person.
0
SPEAKER_01
The Stoics do this a lot.
0
SPEAKER_01
It s can you break down this emotion logically and find what s at the root of it?
0
SPEAKER_01
And I think what s so interesting is like,
0
SPEAKER_01
You compare yourself to someone else, but you don t actually ask yourself, okay, would I actually want to trade places with that person?
0
SPEAKER_01
Oftentimes it s like, hey, I like Joe Rogan s financial success or influence.
0
SPEAKER_01
I wouldn t actually trade places with him for X, Y, and Z reasons, or I m not actually willing to do the things that he did to get there, and yet I m wondering why I don t have the same thing as him.
0
SPEAKER_01
So I try to break down some of those emotions logically.
0
SPEAKER_01
Like you re saying, it s like, look, I got 300 messages, 299 of them are positive, one is negative.
0
SPEAKER_01
Am I really gonna let that one determine how I feel about myself?
0
SPEAKER_01
Maybe the proper response is not to let any of them,
0
SPEAKER_01
change how I feel about myself, good or bad, I think what you say to yourself is, look, you re smart, you re talented, whatever you apply yourself to, you tend to be able to accomplish.
0
SPEAKER_01
So if this thing is actually important to you, if you actually want it, either apply yourself to it and see if you can do it, figure out why it s not important to you, and then stop expecting that you get to have something that you re not working towards.
0
SPEAKER_00
Yeah, that was a problem for me as, I guess I should say, child, even though it probably lasted until I was in my early 20s.
0
SPEAKER_00
And I see this a lot in other folks, too.
0
SPEAKER_00
It s just really hard to imagine the amount of work that people put into something when you re that young because of life experience.
0
SPEAKER_00
I don t think people are bad for thinking that.
0
SPEAKER_00
It s just, you have no idea how much work it is, so when you see other people with that, you think, I want that, and I deserve it because I ve been working toward it for six months now.
0
SPEAKER_00
It s so cliche now that you think, meanwhile, that other person has been doing this for 20 years.
0
SPEAKER_00
now their 15th book is the breakaway number one bestseller that got them where they are.
0
SPEAKER_00
Or the way that I often have to think about it is, well look, this person wrote five books that just crushed it before they started their radio show, which is popular now.
0
SPEAKER_00
Or this person has been doing X, Y, Z for 10 years.
0
SPEAKER_00
Of course they have this huge following online.
0
SPEAKER_00
Why would you think you can accomplish that in a short period of time?
0
SPEAKER_00
And then you just kind of laugh at yourself because you realize how naive or how silly you are.
0
SPEAKER_00
hopefully you get on with grinding.
0
SPEAKER_00
A lot of people give up, actually.
0
SPEAKER_01
Yeah, or it s like, okay, let s say you have some friend who works on Wall Street, and you find out this friend of yours made $4 million last year, and you re like, are you kidding me?
0
SPEAKER_01
I m writing these books, I m working super hard, and I m not even close to touching that, and this jerk makes $4 million a year sitting at a desk in Manhattan, and he s not even that good at it, right?
0
SPEAKER_01
Or whatever you tell yourself.
0
SPEAKER_01
to rationalize how this person shouldn t be as successful as you are.
0
SPEAKER_01
And then what you don t go is, okay, look, this person went to this school, they did this work, they got this job.
0
SPEAKER_01
Could you not have done those things if you wanted?
0
SPEAKER_01
Probably.
0
SPEAKER_01
It s not as if getting a job on Wall Street is a...
0
SPEAKER_01
trillion to one odds, it s a path.
0
SPEAKER_01
And if you pursue that path, you would be there.
0
SPEAKER_01
And it s not like it s too late to pursue that path.
0
SPEAKER_01
You and I couldn t become NBA superstars today because that sort of physical and age constraints have sort of happened.
0
SPEAKER_01
It s like, I guess what I tell myself is like,
0
SPEAKER_01
I made a choice to pursue this thing instead of that thing.
0
SPEAKER_01
Where on earth do I get off thinking that I should have been able to pursue my path, which makes me happy and I chose and wanted, but then I should also get the rewards of someone else s path.
0
SPEAKER_01
It s like, you decide to pursue classical music, you can t sit alone at your hotel room and wonder why there s not mobs of young fans waiting outside to take a selfie with you.
0
SPEAKER_01
If you wanted that, you shouldn t have chose classical music, you should have chose pop music.
0
SPEAKER_01
Life is about choices and trade-off, and you made a choice and a trade-off, what did you expect?
0
SPEAKER_00
I suppose, I think people think they want things that look good in the moment, that s part of the problem, and the distraction of looking at what other people have, that only exists with ego.
0
SPEAKER_00
If you don t care about how other people perceive you, or you care less than you care about, say, mastering your craft, it becomes a really easy calculation.
0
SPEAKER_00
Do I want tens of thousands of screaming young fans?
0
SPEAKER_00
Well, that would be cool, but I d much rather create something that s more meaningful to me like I m doing now than figure out how to remix a Justin Bieber song in that same niche that doesn t appeal to me at all.
0
SPEAKER_00
The trappings seem interesting and fun in the moment, but usually they re not something that you actually want, and yet we find ourselves yearning for them sometimes like we can t live without it.
0
SPEAKER_01
The chapter I m most proud of in Ego is about Ulysses S. Grant, who was a brilliant Civil War general.
0
SPEAKER_01
I talked about him in Obstacle.
0
SPEAKER_01
He s a hero of mine.
0
SPEAKER_01
Well, after the war, he s one of the most famous men in America, and he decides to run for president, even though he knows nothing about politics, and his strengths are not in politics.
0
SPEAKER_01
He runs for president, and he wins, and then he s shocked that it doesn t go super well, and it goes pretty terribly, in fact, although he does get reelected.
0
SPEAKER_01
And then after the presidency,
0
SPEAKER_01
he and his son start a financial brokerage on Wall Street, and it just happened that they basically went into business with a guy named Ferdinand Ward, who happened to be sort of the Bernie Madoff of his day.
0
SPEAKER_01
Grant loses everything, feeling compelled to honor his debts, he actually pawns a Civil War memorabilia to be able to make all his investors whole.
0
SPEAKER_01
There was this letter that Sherman wrote, who was Grant s friend, William Tecumseh Sherman, he was saying,
0
SPEAKER_01
Grant got himself into trouble because he said, quote, he aimed to rival the millionaires who would have given anything to have won just one of his battles.
0
SPEAKER_01
What Sherman was saying is it s like Grant risked everything that he had to impress these people on Wall Street.
0
SPEAKER_01
who were already impressed with him and would have traded all of their millions to have experienced the glory and service that Grant had experienced.
0
SPEAKER_01
One, we don t realize that maybe the other people that we re jealous of or competing with or that our ego is comparing ourselves against, that maybe they re not as happy or rosy as it looks from the outside.
0
SPEAKER_01
Also, we don t realize it s like, hey, we re running our own race here.
0
SPEAKER_01
And if we try to keep pace with other people, and we re not sure what race they re running, that s a recipe for burning yourself out or
1
SPEAKER_00
you re hurting yourself, really.
1
SPEAKER_00
And you ve gotta know the path that you re on, the pace that you re keeping, and in a way, you ve kinda gotta be able to tune everything else out because Seneca has this great metaphor of being on a path and not being distracted by all the different trails and footsteps that intersect that path.
1
SPEAKER_00
That s an easy thing to say, but it s incredibly hard to do, and I think my sort of problems at American Apparel were a result of me being on this path as a writer, but having this sort of side path in my periphery, and as soon as it started to get a little busy over there, I drifted from the path that I was on.
1
SPEAKER_00
I feel very fortunate that I caught myself before I woke up at 40 years old and asked myself, man, what the hell am I doing?
1
SPEAKER_01
So many people do that, and I can just tell you my inbox right now, without looking at it, probably has a dozen things like that from people of all ages, not just 40.
1
SPEAKER_01
There are 20-year-olds that write me that stuff.
1
SPEAKER_01
I feel like I went to school for the wrong thing, and my first line is, thank God you figured it out right now.
1
SPEAKER_00
Right, it s like, it would have been better to figure this out early, but the next best time to figure it out would be right now.
1
SPEAKER_01
Yeah, the best time to plant a tree was 100 years ago, and the second best time is right now.
1
SPEAKER_00
That s exactly right.
1
SPEAKER_00
It s like, if what we re saying about not being distracted by other people, if you re not already aware of it, like I m sorry, but at least wake up to it right now.
1
SPEAKER_00
There s a quote from Publius Sirius, who was this Roman slave who was famous for his proverb.
1
SPEAKER_00
He would say, you know, rivers are easiest to cross closer to their source, right?
1
SPEAKER_00
Because they get wider and deeper and faster moving the further they get away from the tiny little trickle where they begin.
1
SPEAKER_00
And I think it s the same way with these difficult problems in life.
1
SPEAKER_00
It s better that you realize you don t like what you re doing right now than it would be tomorrow or 10 years from now.
1
SPEAKER_01
So super true, and regardless of whether or not you re 40 or 50 and thinking about this, the way to philosophically handle this, and I find myself typing this out a lot in email, is everything you ve done up now and to this point has somehow prepared you for the road ahead.
1
SPEAKER_01
There s probably a billion parables that talk about that.
1
SPEAKER_01
However, it s not just empty words, because if you re 50 and you find out I don t want to do this thing that I m doing anymore, or I never liked it,
1
SPEAKER_01
The clarity that you have at that age from doing that is so sharp and so clear.
1
SPEAKER_01
It would ve literally been impossible for you to have it any earlier than you have it now.
1
SPEAKER_01
It may be even impossible for you to realize it in the way that you do now any earlier than you do in this moment.
1
SPEAKER_01
It would ve been great if you got super lucky, worked really hard in the right direction, and had some Ryan Holiday 19, working with 50-year-old people success.
1
SPEAKER_01
But at some level, Ryan, do you think that you almost got lucky, not with the success like, oh, people like my books, but going, hey,
1
SPEAKER_01
and I found out what I actually like to do, and I really do enjoy this, this is great, wow, I m so lucky I found this when I was 16, 19 years old, instead of stumbling around like a lot of us do.
1
SPEAKER_00
Absolutely, I mean, there s a quote I have from Robert Louis Stevenson in the book where he s saying, knowing what you like is the beginning of wisdom and of old age.
1
SPEAKER_00
And so I ve always felt a little prematurely old in that sense.
1
SPEAKER_00
There s plenty of stuff I have to figure out about myself and about life, but what I want to wake up and work on every morning is thankfully not one of them.
1
SPEAKER_00
I know that.
1
SPEAKER_00
I think that s the other thing that people miss about these theories about mastery or 10,000 hours or whatever.
1
SPEAKER_00
I don t think that I ve mastered what I do.
1
SPEAKER_00
I don t even think I m close.
1
SPEAKER_00
In fact, the reason I work so hard and I create and publish so much stuff is I feel like it s getting me closer to being good at what I do.
1
SPEAKER_00
That s me putting in the hours.
1
SPEAKER_00
People don t realize that it s like, okay, it might be 10,000 hours before you re a certified master at writing, let s say, or a certified master at interviewing.
1
SPEAKER_00
that doesn t mean that you can t make a living at it much earlier, much sooner than that, right?
1
SPEAKER_00
And so, finding that I loved writing probably happened around 18 years old.
1
SPEAKER_00
So I was able to do it.
1
SPEAKER_00
I didn t sell my first book until 24.
1
SPEAKER_00
So there s a good period there where I wasn t getting paid for it or anything.
1
SPEAKER_00
I was still doing things in my life that writing was a part of.
1
SPEAKER_00
And so you can figure that thing out.
1
SPEAKER_00
You can get started on it.
1
SPEAKER_00
It can become viable I think sooner than people think.
1
SPEAKER_01
You re quoting a lot of other people.
1
SPEAKER_01
I m gonna quote you right now.
1
SPEAKER_01
the most critical questions a person can ask themselves in life.
1
SPEAKER_01
Who do I want to be and what path will I take?
1
SPEAKER_01
And I think as far as practical application of this stuff goes, that s a pretty good one.
1
SPEAKER_01
When I was young, I didn t ask myself a lot of that stuff.
1
SPEAKER_01
I sort of said things like, I want to be well off and I want to enjoy my job, whatever.
1
SPEAKER_01
That s crap.
1
SPEAKER_01
That is not who you wanna be, and there is so little information about what path you re gonna take to get there.
1
SPEAKER_01
In fact, there s almost none.
1
SPEAKER_01
I m trying to think if there s even any shred of anything, and they re just kind of these vague goals that end up not getting done and don t spur you forward, because those exist in Narnia.
1
SPEAKER_00
Sure.
1
SPEAKER_00
I mean, and for me, I don t even think I necessarily knew that I wanted to be a writer so much as I knew that I really loved writing, like not me writing, but I loved the written word and I loved books.
1
SPEAKER_00
And so I gravitated towards people who were doing that.
1
SPEAKER_00
And then it happened that, hey, they said I had a little bit of talentedness and that I should pursue it.
1
SPEAKER_00
Gary Shandling, I was listening to him on Marc Maron before he died, and he was saying he wrote these jokes and he showed them to George Carlin, and George Carlin was like, what do you want from me?
1
SPEAKER_00
Are you asking me if this is good enough for you to pursue?
1
SPEAKER_00
And he was like, yeah, I guess.
1
SPEAKER_00
And he was like, yeah, it is.
1
SPEAKER_00
It s good enough for you to pursue.
1
SPEAKER_00
So I sort of got that recognition early on, and I was grateful for that, and then I said, okay,
1
SPEAKER_00
this is who I want to be, and how am I going to get there was sort of the next step.
1
SPEAKER_00
Like, let s say you wanted to be president, right?
1
SPEAKER_00
You don t start working on your campaign at 15 years old.
1
SPEAKER_00
You go, okay, let s look at the history of presidents of the United States.
1
SPEAKER_00
What traits do they tend to have in common?
1
SPEAKER_00
Okay, maybe some of them had military service.
1
SPEAKER_00
A lot of them went to really good schools.
1
SPEAKER_00
or they started by getting elected to a small office in their town or region, or they were successful in business.
1
SPEAKER_00
And then you go, okay, so in order to do this thing way off in the future, I ve gotta break it down into sort of composite pieces that are, when they come together, will qualify me or allow me to be president if everything goes right.
1
SPEAKER_00
it s not walking around going, I m gonna be president.
1
SPEAKER_00
It s like, hey, I gotta be a congressman.
1
SPEAKER_00
So my goal for the next 15 years is to work myself into a position where I could run for a congressional seat.
1
SPEAKER_00
And so I think what I sort of thought is, okay, I wanna be a writer, and I remember I asked a writer I knew, I worked for Tucker Max early on in my career, and he said, look,
1
SPEAKER_00
I m not that great of a writer, but I have really good material because I ve lived sort of a ridiculous life, right?
1
SPEAKER_00
My stories compensate for my writing.
1
SPEAKER_00
So he s like, writers live interesting lives.
1
SPEAKER_00
And so I said, okay, I m gonna go do stuff that s gonna teach me or give me material to write about.
1
SPEAKER_00
And I went and I worked at American Apparel and there was a lot of experiences there.
1
SPEAKER_00
And I also happen to learn about marketing, which came in pretty handy in marketing my own stuff.
1
SPEAKER_00
But my first book was a book about media and marketing, which is what I developed expertise and unique knowledge in.
1
SPEAKER_00
And so I think for writers,
1
SPEAKER_00
so many of them are like, oh, I gotta go to school to learn how to write, and I think they re just thinking about it totally the wrong way, just like, you know, you said, okay, I wanna be happy in what I do, and I wanna be financially well off.
1
SPEAKER_00
Those people are like, lawyers make a lot of money, I m gonna be a lawyer.
1
SPEAKER_00
You know, it s not well thought out.
1
SPEAKER_00
That was my actual plan, by the way.
1
SPEAKER_01
I was like, yeah, sweet, law school, I don t have anything else to do.
1
SPEAKER_01
I ll probably just do that.
1
SPEAKER_01
And that s why there s so many unhappy lawyers, I think.
1
SPEAKER_01
Oh, yeah.
1
SPEAKER_01
It s a high-performing mindset where you go, I killed it in college, or at least I think I did pretty well.
1
SPEAKER_01
I wanna do something, I m not sure what it is, but it s definitely gonna involve some sort of high performance.
1
SPEAKER_01
I didn t take the pre-med prereqs.
1
SPEAKER_01
I m not an engineer.
1
SPEAKER_01
I m not really a computer science kind of person.
1
SPEAKER_01
People say that I argue a lot and that I m intellectual, so I should totally go into law.
1
SPEAKER_01
That is 98% of the people in law school.
1
SPEAKER_01
you fall into that and then dot, dot, dot, we are where we are, right?
1
SPEAKER_01
It doesn t even bear explaining how many lawyers are unhappy.
1
SPEAKER_01
It s like the most unhappy profession.
1
SPEAKER_01
Somehow dentists are also miserable, don t really get why.
1
SPEAKER_00
I think it s a very similar vocation in that no one s like, oh, I love teeth.
1
SPEAKER_00
It s more like my dad said dentists make a lot of money and it was relatively easy and a set path and I did it.
1
SPEAKER_00
They didn t actually meet any dentists
1
SPEAKER_00
or have any sort of youthful experiences.
1
SPEAKER_00
There s plenty of happy lawyers, and those are lawyers probably, I would imagine, who got into it because they actually loved the law, or they loved the field in which they practiced law.
1
SPEAKER_00
And that s a fundamentally different path than saying, lawyers make lots of money, I m qualified on paper to be a lawyer, so that s what I m gonna spend the next 50 years of my life doing.
1
SPEAKER_00
It s like, hey, lawyers drive nice cars.
1
SPEAKER_00
I m someone who deserves a nice car.
1
SPEAKER_00
So I m going to do that.
1
SPEAKER_00
You can see where ego plays
2
SPEAKER_03
is it s part there too.
2
SPEAKER_03
billions and billions of dollars runs that hedge fund, he s maybe not directly competing with all these other folks, but there are hints of it where he s, oh, you gotta go talk to so-and-so, ah, I don t wanna have to make a deal with that jerk face, you know, and there s all these egos, even these guys who have billions and billions of dollars and can buy anything they want and it s just obscene and they fly private in their own plane to see concerts and hang out with the band, they re still like, I m not satisfied, I gotta make more, I gotta beat other people who are at my level, it s completely ridiculous and it s never-ending.
2
SPEAKER_03
You re right, yeah, you ve gotta go to that dentist s office, have that internship, you gotta have that legal internship, but getting back to the topic of ego in the first place, are high performers maybe more susceptible to ego?
2
SPEAKER_03
It seems almost like the examples in your book tend to focus on that, possibly because there s more literature about it, or maybe it s just more interesting, but it almost seemed like people with ambitions and talents and drives and potential, it s almost like ego comes with the territory.
2
SPEAKER_02
It absolutely does, and it also comes with the territory of unambitious people, I m sure, but as you said, there s not a lot of literature around some loser who s also an egotist who never gets off his couch.
2
SPEAKER_02
No one s writing about that guy.
2
SPEAKER_02
There s not many studies about him, so it s hard to make an example out of him, but it s two things.
2
SPEAKER_02
I think one, the more you re trying to accomplish
2
SPEAKER_02
the more ego can function much in the way of a drug that sort of numbs you from some of the fear and pain that might come along with that difficult task that you re pursuing.
2
SPEAKER_02
And then I think also the stakes are higher, so ego
2
SPEAKER_02
is more easily seen as a culprit or a negative influence.
2
SPEAKER_02
In Billions, one of my favorite lines in the entire show is, he makes some huge bet that everyone warns him against, over and over again, don t do this.
2
SPEAKER_02
And it blows up in his face and he loses a lot of money.
2
SPEAKER_02
And Wendy asks him, she s like, hey, what were you doing?
2
SPEAKER_02
And he s like, look, when people tell you you re Superman long enough, you start to think you can fly.
2
SPEAKER_02
And so I think that s the other part, is that to have some ambition.
2
SPEAKER_02
You created your show from nothing.
2
SPEAKER_02
and you created it before podcasting really existed, before it was a big thing, when people probably said podcasts would never amount to anything and that you should go get a job or whatever, but you didn t listen to them and you created something out of nothing.
2
SPEAKER_02
And so, in a way, that s people telling you you can t fly, and then you flew, and so now, all of a sudden, you think that you re better than everyone else, right?
2
SPEAKER_02
That s very seductive or tempting, right?
2
SPEAKER_02
It s like, even with my books, right?
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It s like, let s say my editor was wrong about something, or told me something, and I disagreed, and I went with my gut, and I turned out to be right.
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The problem is when you say, okay, I m right always from now on.
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and it s especially true for people who have done feats that are physically impressive.
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Hey, I was the best fighter in the world, or something, and then you re like, now I m invincible, no one can touch me.
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And then it s like, hey, actually they can, and we re all fallible.
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When you have big ambitions, ego is bad.
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But it s when you have ambitions, and you fulfill that ambition, that ego is particularly potent and dangerous,
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because it can mess with your head for the next venture that you embark on.
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people who listen to the show kind of know, I m not gonna blow sunshine up your skirt.
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Neither are any of the coaches.
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AJ and Johnny are not gonna do that because it s not good for you.
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And we ve seen it happen to other high performers especially, and young people.
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It s funny because ego s this weird affliction that kind of young people have it and then you sweep the doorstep or you sweep the floor as you say in the book.
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You take the blow and you get beat down a little bit in the beginning of your career and you start to work yourself up and then, oh man, that floor is getting dirty again.
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Sometimes you slip and fall on that dirty floor and you realize, oh man, I ve been ignoring this the whole time.
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I thought I had this handled.
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And you look back at when you had your last reality check and it was like a decade ago or something like that, and you go, oh crap, I brought this on myself.
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And maybe there s the ego in thinking that you have it handled.
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That s the most insidious part of it.
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It s like, you and I were both there, we saw someone talk recently, and he said several times, like, I m very self-aware.
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My strength is that I m very self-aware.
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To me, that s like the ultimate form of
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unawareness or the ultimate form of ego, right, is thinking that you ve got it locked down and you re set.
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Everyone else struggles with this thing, but you don t.
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Like, I find there s a lot of people who are like, you know, I m not one of those guys that s out there beating my chest, you know, saying that I m better than everyone else.
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And it s like, yeah, you re the guy sitting on the bench, whispering to the person next to him that you re better than everyone else, right?
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And it s the same thing, it s just expressed in a slightly different manner.
2
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Why is ego so dangerous?
2
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It seems obvious because we don t like egotistical people or egotistical people alienate themselves, but there s actually a lot of very specific dangers that come from it.
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One of them that was really striking for me was ego is the enemy of what you want and what you have.
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For example, mastering a craft.
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Mastering a craft is something that I think about all the time.
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I wanna be the best interviewer.
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You know, one of the greatest shows around.
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If I m thinking I ve already made it, that s totally not gonna happen.
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I think that s right, especially because the craft is always evolving, especially now that technology has democratized it in a sense that there s so many more people doing it and innovation is so much easier, right?
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So maybe 50 years ago, you just needed to work on something a couple years and then you could coast the rest of your career.
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but it s so much more competitive and it s so much harder, and I think if you think that you re as good as you can possibly get at something, you re probably right, because you can t get any better.
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There s an Epictetus quote where he s like, one cannot learn that which they think they already know.
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I think that applies to what we do.
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If you have decided that you ve mastered something, the second you think that, your abilities have been sort of flash frozen, and I think they become very brittle after that.
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Whereas someone who sees themselves as a perpetual student of what they do, and that it s something that one cannot even dream of mastering even over the course of a life, but that one can get incrementally better every single day, that person is on a journey that I think will take them much further.
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I think you see this in sports especially.
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It s like, okay, you re good enough to be in the NBA, but now you don t have a good enough jump shot.
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And then you add a jump shot to your game, now you ve gotta add defense.
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Then you ve gotta add rebounding.
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And then you ve gotta add leadership.
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Like every task that we do, once we get good enough at it, opens up other things.
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You become a really good interviewer, now all of a sudden you ve gotta figure out how to run the business that the interviewing has facilitated.
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And as soon as you start to expand that business, now you have to figure out how to manage some other element.
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that isn t always obvious to someone when they re just starting out.
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I think they think, hey, I just gotta get good at this one thing and then I m set for life.
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It can be tough and it s especially tough for successful people who can t maybe see what ego prevents them from doing because all they can see is what they ve already done.
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You write about this as well in the book.
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There s a lot of people who, they only look in the past at what they ve created, and they re kind of leaning on this to the point where it s impossible to do anything with them because they re constantly living in the past.
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They re living in the moment that they won the World Series 20 years ago, and it s pathetic, but it s also extremely irritating and difficult, and they end up achieving so much less because of that.
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Right, it s like you peaked in high school, dude.
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No one cares about the touchdown you threw in the semi-conference finals or whatever.
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Every day you re starting from scratch, basically, I feel like.
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And so that attitude, that sort of self-obsession or self-satisfaction, not only endangers what you have because, as they say, if you re not growing, you re dying,
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but it also prevents you from adding to those accomplishments because you ve lost sort of the essential hunger and humility and work ethic required to do new things.
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One thing that you write about ego doing is it keeps us in our comfort zone.
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It s the reason we keep ego around in the first place because one question that comes to mind is,
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If this is so bad, how is it a problem for so many people?
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I mean, if it s so bad, why do we keep ego around?
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And the answer is that it s comfortable.
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But why is that in itself also bad?
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Well, so here s where ego works.
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Especially when we re dropping out of college was something I did at 19, 20 years old.
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It was terrifying.
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I was essentially putting all my chips in the middle of the table before I could grow a beard.
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and my parents said, you re going to fail, this is an awful idea, don t do this.
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Conventional wisdom said, don t do this.
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A bunch of other factors.
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Would it have been nice to have been able to tell myself, you re a badass, this is going to be amazing, this is going to be the best decision you ever made, and everyone who doubts you is an idiot.
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and it s gonna be smooth sailing from here on out, and they can kiss your ass, and that s the end of it, right?
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It would have been nice to have been in a cocoon of my own ego, in the sense that it would have mitigated some painful emotions and feelings.
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And yet, and this is sort of the irony, it also would have made it much less likely that any of those things would have turned out to be true, right?
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I would have been much less likely to succeed
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I would have been much less likely to be able to turn this into something, in the same way that doing drugs is a nice way to address feelings of existential emptiness, worthlessness, or pain, or anguish, or sadness, or fear.
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But it s not actually solving any of those problems.
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So in a way, it s just actually making you dependent on those feelings, or worse, making you incredibly fragile in regards to those feelings.
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And so, for instance, sitting down to write a book, terrifying.
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Steven Pressfield calls this the resistance.
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The resistance we feel when we re pursuing any creative project.
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Ego is a nice way to blow right through resistance.
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It s also a nice way to make something that is inauthentic and untruthful and doesn t resonate with people.
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What ego is doing is mitigating in the short term this unpleasantness and keeping us in our comfort zone, but the reality of creative work and entrepreneurial success and even general human happiness and flourishing is that you have to wrestle and feel precisely those feelings.
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There s that awesome Louis C.K.
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bit where he s like, the second you feel uncomfortable, you want to reach into your pocket and pull out your phone so you don t have to feel that, but the whole point of life is to feel those things and to push through them.
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SPEAKER_00
So it s a short-term fix with long-term consequences that are pretty dire and crappy, even in the same niche, right?
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SPEAKER_00
Like, your career can be served short-term by having that ego pushing through that resistance, but long-term, if you keep the ego going, it will inherently limit what you re able to do and create.
3
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Yeah, I mean, look, one of my favorite bands is Alice in Chains.
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Me too.
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That s so random.
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Yeah.
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So there s no argument.
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The drug abuse and the addiction fueled the darkness and the beauty and the weird perspective of the music.
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But it ultimately
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killed the guy responsible for it, so I m not sure that s like a worthwhile trait.
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Is there probably another better way for him to investigate and explore that darkness in the music?
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And so when you say like, look, there s lots of successful people with huge egos, yeah, there s lots of successful musicians who are drug addicts, but ultimately the addiction, however helpful it might have been in the short term, is not worth it in the long term, or worse, it has fatal consequences in the long term.
3
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Yeah, there s definitely something to be said for the drug addiction angle of a lot of this.
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And it s not just drugs, actually.
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It s any kind of addiction or any kind of sort of side effect of this that can come as a result.
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Yeah, a lot of entrepreneurs are very manic.
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That doesn t mean that mania is the good thing.
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On the whole, it s usually a recipe for making bad mistakes or doing sloppy work or rushing in or through things.
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You ve gotta realize that it s usually they re successful sort of despite the mania or that the mania is
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a double-edged sword.
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Going back to the comparison angle, do you find that ego is worse or exacerbated by the vanity, or the accessibility of internet and tech that creates almost this vanity comparison where, oh man, this person did this, or this person just sold their company, and now everyone s talking about it, whereas 20 years ago, that person could have sold their company, you might have heard about it,
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through friends a few days later, but you wouldn t see it in everything that you re doing on Facebook, on Twitter, in your newsfeed, on TechCrunch, everywhere that you get your news.
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It wouldn t happen all at once and be this sledgehammer blow.
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It would have been a trickle effect where you might have actually been happy for the person.
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Instead, you find yourself thinking that you re a huge failure or that you deserve what they have.
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I think social media takes these sort of universal, timeless human concepts and amplifies them.
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I could look at my own Instagram feed and be jealous.
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I d be like, oh, that s awesome.
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Because it s a deliberately edited, filtered version, selective take on what my life is like.
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It s so easy to forget that that s true for everything we see on social media for every other person.
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I know this couple, and it s a very unhealthy, bad relationship.
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But every time they re fighting, they post positive pictures on social media, essentially reassuring themselves, which they re fine to do, that everything s okay.
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It s interesting to me that people who don t know that this is happening probably see those things and feel bad about themselves.
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They re like, why isn t my relationship like that?
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My girlfriend never says anything like that, or I don t say that about the person that I m with.
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That s because what you re looking at is a lie.
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It s posturing and it s projection, it s not true.
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And so I think just the idea that you re like, oh, this person has more followers than me.
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Cult leaders were the only people who used to have followers 20 years ago, but now it s like,
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a legitimate concern, and you get a daily snapshot of how many of them you have, these are not things that the human brain is really prepared to process, and if you don t parse through it and think about it properly, it can really mess with your head.
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I see this happening as well in businesses or in paths people take in their career.
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You wrote, we see risk-taking, swagger, and successful people in the media and, eager for our own successes, try to reverse-engineer the right attitude and the right pose.
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And I see this 2020 hindsight BS all over the place, especially living in Silicon Valley.
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You live in Austin, which is Silicon Valley off-campus, whatever, South Campus, but it s very, very similar, I would imagine, in some ways.
3
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A lot of entrepreneurs and a lot of companies romanticize this.
3
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They make it a story that makes us or them look good, and then everybody s trying to go, okay, if I want that, I ve got to have the right attitude, the right pose.
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You find this causal relationship that isn t really there, and this is dangerous.
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Yeah, it s like how many people are trying to be Steve Jobs?
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In fact, Steve Jobs was actually a terrible CEO.
3
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He was a brilliant, creative mind who created some ideas and a company that it compensated for just how bad he was as a manager and as a human being in a lot of cases, right?
3
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And as you said, you don t realize all the work that went into being the guy who picks his outfits in advance and parks in handicapped spaces and blah, blah, blah.
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There s a story from Plutarch, I m not even going to try to do the names and get it wrong, but basically he was saying that after Alexander the Great died,
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all the potential heirs to his kingdom and throne, all his generals who wanted to be the next Alexander the Great, they mimicked the way that Alexander would walk and the way that he would dress and the way that he trimmed his beard.
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And Plutarch was saying, all of them except for this one general who mimicked Alexander the Great in how he led troops into battle.
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It s like you guys are missing the point.
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You re like thinking about how Steve Jobs wore the same outfit every day or the glasses that he wore as though that had anything to do with inventing the iPod.
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It s missing the point.
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You see that a lot, right?
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Like, ah, I started to wear only the white t-shirt and jeans so I don t have to think about what I want to wear.
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And it s like, well,
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That s really cool from Mark Zuckerberg.
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It s a funny quirk.
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Yeah, maybe it does take away from him making a decision that he just really hated every morning, and nobody can say, why do you wear the same outfit every day now?
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Because they know that s his trademark.
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On the other hand, that s not the reason he invented Facebook.
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Those were things that, if he did them before,
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everybody would say this person is insane.
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And we all know crazy people that do crazy things.
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It only becomes brilliant when they have this scorecard that backs that up.
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Otherwise, they re just creepy or weird or bizarre or have social issues.
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Lighthouses are on the edges of, I guess, jutting out rocks and things like that in the water to lead ships around them.
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If you just built a lighthouse in a random place or maybe
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300 yards behind that rock.
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Ships would crash into it all the time.
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Nobody would ever do that.
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And yet, we re using a lot of these weird quirks or a lot of these sort of different paths that people say they have or that we re trying to figure out what they do to reverse engineer it.
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We re just building a lighthouse really far away from the coast that s gonna cause our own ship to crash later on.
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and we re kind of looking at this as false GPS.
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In fact, a real world example I was talking with, do you know Mimi and Alex Icon?
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So they have this really successful YouTube channel, Instagram, I think they sell a bunch of different things like hair extensions, and they re super cool, super nice people that everybody loves.
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And I was talking with somebody else, this guy, like a junior professor or something at maybe London School of Economics, some really interesting, high-performing school loaded with smart people that analyze things.
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And he said, yeah, one of the things I thought was really interesting, we did a case study on Mimi and Alex Aikon s YouTube channel.
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In every shot, they have a variety of at least nine colors, including flowers that are always multicolored, and the flowers represent this, and the flowers get people looking at this in this way, and they always match with her dress, and she s doing that on purpose to show XYZ, and I sat down with Mimi and had lunch literally the day after that talk, and I explained that to her, and she just started laughing, and she goes, I just like flowers.
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That s why I have them.
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Totally, and so you re not only missing the point, you re sort of confusing causation and correlation.
4
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The equivalent for me that I see a lot of people do is they read these websites that s like about writer s routines.
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You know, like, here s how Hemingway typed, or here s what so-and-so did.
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You can fall down this endless rabbit hole of studying like how-to and best practices and hacks and all this stuff instead of sitting in the chair and writing.
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or God forbid, having something unique and interesting to say.
4
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And so people don t do that.
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It s much easier to pretend and ape the style of a successful person than it is to get at the root of what made them great.
4
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Yes, exactly, and of course we have to keep in mind exactly where we re going, and oftentimes we can t deduce that from where somebody else is now, because they can t really do that.
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People often ask me, how do I launch a podcast?
4
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How do I become a better interviewer?
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And I m just thinking, I literally,
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have no idea where you would even begin other than cliches like practice makes perfect and maybe read this one book that maybe kind of helped me, although when I read it, I m not sure what I got out of it.
4
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It s hard to say there s this clear backwards path, and especially when it comes to things like how do I launch a podcast?
4
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I m the worst person to ask because I launched in 2006 with AJ when all you had to do was upload things to iTunes.
4
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There was no launch.
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And the technology we had back then, you d never use the same hosting we used back then.
4
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You d never use the same WordPress, if that even existed back then, type of plugins or whatever to launch the site and the show.
4
SPEAKER_00
It s ridiculous.
4
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Twitter wasn t a thing people used as far as I know.
4
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Nobody was using social media to market stuff.
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I think I was on Facebook because I had an invite because I went to a certain school.
4
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There was no such thing as influencer online at that point.
4
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You can t look backwards and emulate what people are doing because even they can t tell you.
4
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what happened, and you can get the smartest people in the room, like the London School of Economics, together, and they ll say, one of the keys is you gotta have flowers in every shot.
4
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And it s just completely speculative.
4
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Very rarely are people able to reproduce the effect based on those analyses.
4
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It s almost never happened, as far as I know.
4
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And I think it s also really humbling for you, once you have been successful, to remind yourself, like, hey, I wasn t some genius that figured all this out, that knew exactly where I was going.
4
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I took a chance, that chance got a little bit of validation, and I explored it, and iteratively, I built this business, or this empire, whatever it is.
4
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hey, I m the expert, I did this, you should listen to me tell you how you should do it.
4
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And it becomes this cycle where all of a sudden your complicated, nuanced, up and down history becomes this really smooth, gratifying, impressive narrative about how you can predict the future, basically.
4
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How do we control the ego?
4
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We know it can be controlled.
4
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It s not a power you re forced to satiate at every turn.
4
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How do we start to manage these things?
4
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Are there practical exercises, questions we can ask ourselves, things like that that we can take after the show and go, alright, figure this out, figure that out, ask yourself this all the time.
4
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What can we do that s practical and applicable?
4
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There s not like, hey, here s the ego checklist and if you run this every day, maybe someone can make that, I don t know what it is.
4
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But my point is that having this discussion and thinking about these things inherently humbles the ego and keeps it at bay.
4
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Are there sort of certain career paths that I advise?
4
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Sure, if you work with or surround yourself with people who are much smarter and more successful than you.
4
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For me, I worked with Robert Greene and every day I would wake up and work for this author who s 1,000, 100 times better than me.
4
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I never had the opportunity to think, oh man, I ve got this, I m amazing.
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Because I could see every day that there was stuff left for me to do.
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So it s surrounding yourself with the right people
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subsuming yourself in an inherently difficult, ever-changing task.
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I think that s a big part of it.
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One of my favorite sections of the book I talk about, this thing that French philosopher Pierre Hiddeau calls the oceanic feeling.
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And basically he s saying it s like,
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Look, when you re alone on a beach next to the ocean, you naturally feel very small for a second, right?
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Because it s this unending, unstoppable force of which you could be tossed around like a cork inside of.
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I think being in nature, experiencing things that are much bigger than you, of which you are a tiny,
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infinitesimal point is also a compelling way to attack ego.
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I m a big proponent of physical exercise.
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I do some form of strenuous physical exercise every single day.
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Why?
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Because it gives me a task to complete that is hard and difficult and I have to be fully present to do.
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My mind can t wander.
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I can t be sidetracked.
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It s like I have to do this thing and it kicks my ass when I do it.
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I think there s little practical things here or there, but really it s asking yourself these tough questions and probing and looking inward, reexamining your priorities and principles on a regular basis that I think does the majority of the heavy lifting for ego.
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So sitting down and thinking about maybe what s truly important to you and then taking steps essentially to forsake the rest and also to focus on getting to that goal instead of finding these proxies.
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With social media, for example, it started off as people showing off on social media and now social media is the actual accomplishment.
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It s no longer, here s this thing I did, or that I m doing right now, it became, here s what I m eating right now, and then it became, I need to post about this because I m curating online, or whatever.
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You start to lose yourself in these proxies, thereby never really accomplishing much of anything.
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Yes, and I think asking yourself, who do I want to be?
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What are the behaviors that I like or admire?
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And holding yourself up against some sort of model.
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I m not a religious person, but I could see the value in a what would Jesus do bracelet, right?
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It s like, okay, this is the platonic ideal.
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This is what I sort of guide my behavior against.
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If you were to cancel this interview two minutes before, be like, Ryan, I don t have time for this, I don t wanna talk to you anymore, blah, blah, blah.
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You did something rude or offensive, naturally you re gonna have the, what?
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You re gonna feel that defensiveness, you re gonna feel your own ego, how dare he talk to me this way?
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You re gonna have that reaction really fast, right?
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And I m not saying that,
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if you meditate 10 minutes every morning, that s magically gonna go away and you re never gonna feel that.
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What I m saying is, can you have enough discipline to hit pause for a second and then decide rationally and calmly and without ego how you re going to respond to this, right?
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What are you gonna do about this?
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and is your response gonna make things better or is it gonna make things worse?
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And I think where ego is the most problematic is for people who are so busy and so active and they have so much initiative that they re just jerked around by their emotions all the time and that those emotions often bog them down in pointless fights and battles and conflict.
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What about subjecting ourselves to that uncomfortable feeling, the defensiveness that we feel when our assumptions are challenged or when we feel, not attacked, but challenged in a way that gets us outside of our comfort zone?
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Should we be looking for opportunities to essentially change our mind?
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Not just change your mind, but be challenged on the things that you hold dear.
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reading books that are above your level, or are written by people that you disagree with, or having conversations.
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Like, I try to think, it s like, okay, I m gonna go talk to this person.
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I very much disagree with them on pretty much everything.
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My goal in this conversation is to not lose my temper.
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Can I just accomplish that?
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And I m gonna focus sort of exclusively on getting that out of this given scenario.
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So I think there s value in making sure that you re not existing in a bubble of your own comfort, where you re not just being told everything that you want to hear all the time.
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Okay, that makes sense.
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So bringing ourselves into a place where we ve, maybe you don t even have to cultivate this, a circle of people or friends or mentors that will give you honest feedback and not just feel like they need to placate you.
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Yeah, I mean, look, that s gotta be the reason that a lot of really successful, let s say, musicians will release an album and be like, what were they thinking?
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Who is this for?
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It s probably lost that connection to their fan base, to their audience.
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And I think every creative person and entrepreneur s gotta worry about that.
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how am I keeping that fluid, real connection?
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It s not that I m, hey, I m putting my finger to the wind and just letting them lead me, but also, how am I making sure that I don t think that I ve got the Midas touch and everything I touch turns to gold?
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from the book is whenever you feel pride, you can ask, what am I missing right now that a more humble person might see?
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And more importantly, what am I avoiding or running from with bluster, franticness, and embellishments?
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That s powerful because you have to ask that question right in the moment when you really don t want to.
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Totally.
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I mean, one of my favorite books is The Gift of Fear by Gavin DeBecker.
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I just read that yesterday.
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That s so funny.
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Really?
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Well, so he has a question in that book.
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He s saying you should ask yourself when you re worried or anxious, what am I missing going on around me that would keep me safe because I m consumed with this anxiety or worry?
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And I think you can apply the same thing with pride.
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If you tell yourself that was perfect, I did an amazing job,
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you re going to feel that sort of surge of pride within you.
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What you re not seeing is the thing you could have done 1% better or a little bit difficult.
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You know, I tell the story in the book about the Patriots drafting Tom Brady.
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They took Tom Brady in like the sixth round.
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He was like the 200th plus pick of the entire draft.
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They didn t even really want him.
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It was just sort of there.
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So they could have felt pride when two years later they won the Super Bowl.
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They had probably one of the best picks in the history of football in terms of ROI.
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As he would go on to play 12 plus seasons, win multiple Super Bowls, multiple MVPs, multiple championships, you could feel pride in that accomplishment.
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What they felt instead was, man, how was our picker so off?
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How do we let this guy wait until the sixth round?
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I think that s a much more constructive attitude, particularly for an organization.
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As an individual, you want to make sure you re not kicking yourself all the time.
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The opposite of pride is not disgust and self-loathing.
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The opposite of pride is just awareness and honesty.
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And so I think you ve got to ask yourself, hey, is pride the most constructive feeling I could have right now?
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Ryan, thank you so much for your time.
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This has been amazing.
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Thanks, man.
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It s always good to talk to you.
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really interesting episode.
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Went a little bit longer than usual, but I m fully okay with that.
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I think this is one of those problems that creeps up on us, and that s why it s so insidious.
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And when it does, that s unfortunately when it s the hardest to catch ourselves in the moment and do the right thing that is required in order to manage it.
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So it s all that constantly sweeping the floor.
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There were a lot of notes I took in that book.
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We went through just a couple of pages, and I think we went through less than one eighth
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of what I had actually prepared for the show.
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So there s a lot there.
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If you like Ryan s books, you ll love this one.
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If you don t know Ryan s books, you can go ahead and start with this one as well.
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I think it s a great intro to his work and to his writing, and it s very, very well done.
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If you enjoyed this one, don t forget to thank Ryan on Twitter.
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We ll have that linked in the show notes as well as the other resources mentioned on the show, and you can tap our album art in most mobile podcast players to see the cheat sheet for this episode, and we ll link to the show notes directly on your phone as well as a link to the book, of course.
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I m also on Twitter, at theartofcharm.
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It s a great way to engage with me, and I post a lot of things there that I don t share on the show or anywhere else.
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Also, don t forget about the challenge at theartofcharm.com slash challenge, or text charmed to 33444.
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That s C-H-A-R-M-E-D to 33444.
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We ll take you step by step, improving your networking and connection skills, and inspiring those around you to develop a personal and professional relationship with you.
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We ll also email you our Fundamentals Toolbox that I mentioned earlier on the show.
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I m also doing regular videos with drills and exercises to help you move forward every single week.
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It ll make you a better networker, it ll make you a better connector, and it ll make you a better thinker.
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That s theartofcharm.com slash challenge, or text charmed to 33444.
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This episode of The Art of Charm was produced by Jason DeFilippo.
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Jason Sanderson is our audio engineer and editor.
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Show notes on the website are by Robert Fogerty.
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I m your host, Jordan Harbinger.
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Go ahead and tell your friends, because the greatest compliment you can give us is a referral to someone else, either in person or shared on the web.
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Now stay charming and leave everything and everyone better than you found them.
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Thanks for listening to the Art of Charm.
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Get more confidence, relationship skills, life hacks, and more at theartofcharmpodcast.com.