Ego Is the Enemy – Ryan Holiday’s Wake-Up Call

Ego whispers lies, about our greatness, our entitlement, our invincibility. This episode breaks down how recognising and rejecting ego can unlock real growth and long-term success.

Episode Transcript

(00:00):
Welcome, curious minds, to another deep dive.
Have you ever experienced that dizzying sensation of being
absolutely on top of the world, only for it all to just kind of
unravel beneath your feet? Oh yeah, or maybe you've watched
someone else, someone with just undeniable talent, spectacularly
stumble. Exactly.
And you're left wondering how. How did that even happen?

(00:22):
If so, you're tapping into this fundamental paradox of human
ambition, the very drive that propels us to these dizzying
heights. Well, it often carries the seeds
of our own destruction. It's a profound truth, isn't it?
That initial spark, you know, that fierce belief in ourselves.
It can be incredibly powerful for getting started, Absolutely,

(00:43):
essentially. But left unchecked, it can blind
us, make us believe we're invincible.
Or, you know, that the usual rules simply don't apply to us.
And that, my friends, is precisely what we're going to
unravel today. We're drawing deeply from Ryan
Holiday's incredibly insightful book Ego is the Enemy.
Such a great title. Isn't it?
And this book has truly sparked a conversation, and for for

(01:05):
excellent reason. When you see who's endorsing it,
it just speaks volumes. It really does.
We're talking about literary giants like Steven Pressfield,
you know, the author of The War of Art.
He calls Holiday one of his generation's finest thinkers.
High praise. Very high praise.
Then there's Austin Cleon from Steel Like an Artist.
He praises it as packed with stories and quotes that will

(01:25):
help you get out of your own wayoffering, as he puts it, a
prescription Humility. And what's particularly striking
about those endorsements and others, too, is how broadly they
resonate. Right.
You've got George Raveling, a Hall of Fame basketball coach,
saying it's a must read for every athlete, aspiring leader,
entrepreneur, thinker and doer. Wow.

(01:47):
That covers pretty much everyone.
It does, and Mark Echo, the founder of Echo Untold.
He issues this stern warning that ego wrecks promising
creative endeavors and urges us to read this book before it
wrecks you. Strong words.
Yeah, these aren't just like polite nods, they're really
sincere endorsements from this wide spectrum of fields.

(02:10):
Writing, art, sports, entrepreneurship, even
psychology, with Doctor Drew Pinsky calling it profoundly
pertinent to all our lives. It just really highlights that
the challenges posed by ego aren't confined to, you know,
any single domain. It's universal.
It's true. And you know, one of the really
compelling aspects of this book is that the author isn't just

(02:32):
lecturing from some ivory tower.Not at all.
He shares what he calls his painful prologue, openly
admitting he's experienced ego at each of its stages in my
short life. Aspiration, success, failure,
and back again and back again. It takes guts to admit.
It does. Imagine dropping out of college
at 19, becoming a young executive advising huge rock
bands, then having your own bestselling book with your face

(02:55):
plastered on the cover by 25. That's a of descent.
He built a successful company, gained influence, a platform,
resources. That's a seriously fast climb.
And this is where his self-awareness really, really
shines through. He readily admits the
temptation, you know, to craft astory, to kind of round off the
edges and make it sound like some.
Like some heroic journey. Exactly like a herculean

(03:18):
struggle for greatness against all odds.
But he immediately just cuts through that, revealing the
stomach turning drops in. The mistakes, all the mistakes.
This refreshing honesty. It really is.
He talks about public eviscerations, losing his nerve,
the fleeting nature of being a bestseller, a book signing
attended by literally one person, his company tearing

(03:39):
itself apart not once but twice.Wow.
He genuinely wish this book had existed for him earlier, and it
reinforces his deliberate choice, I think, to focus on
philosophy and these timeless historical examples rather than
just his own personal narrative for the bulk of the book.
Right, that gives it that universal resonance, doesn't it?
It's not just his story. Exactly makes it timeless.

(04:01):
He recounts his period around 2014, when his world just seemed
to fracture. American Apparel, where he'd
done a lot of his formative work, was teetering on
bankruptcy. It's charismatic founder, whom
Holiday really admired, got fired and ended up like,
sleeping on a friend's couch. The talent agency that had given
Holiday his start facing lawsuits.
Another mentor, someone he'd really looked up to, just

(04:24):
imploded. These were the very people he'd
shaped his life around, he says.And suddenly their foundations
were just crumbling. And it wasn't just an external
crisis for him either. He acknowledges neglecting
problems in his own life, finding himself stressed and
overworked. Right, He admits he'd handed
much of his hard earned freedom away because he couldn't say no

(04:45):
to money and the thrill of a good crisis.
He describes himself vividly as wound so tight that the
slightest disruption sent me into a sputtering, inconsolable
rage. Wow, that's.
Raw. Yeah, his work, which used to
flow easily, became labored, andhis faith in himself just
crumbled. It really highlights how the
very drive that brought him success almost destroyed him.

(05:05):
It reveals that that dark side to ambition.
So how does the author define this slippery destructive force
then? Holiday's definition of ego is
wonderfully straightforward, very actionable.
Which is helpful. It is, he says.
It's an unhealthy belief in our own importance, arrogance,
self-centered ambition. Simple but powerful.

(05:25):
He paints this vivid picture, calling it that petulant child
inside every person, the one that chooses getting his or her
way over anything or anyone else.
We all know that child. We do think about it, that
insatiable need to be better than, more than or recognized
for far beyond any, you know, practical utility.

(05:46):
That's ego. That casual yet really impactful
definition cuts through a lot ofthe academic jargon I think it
does. And it echoes the wisdom of
people like the legendary football coach Bill Walsh, who
wisely warned that self-confidence becomes
arrogance, assertiveness becomesobstinacy, and self assurance
becomes reckless, abandoned. It's a fine line.
A very fine line. The book suggests this isn't

(06:09):
just like a character flaw. It's this pervasive force, like
a hidden current, that sucks us down, like the law of gravity,
suddenly pulling us off course without us even realizing it.
And the problems this ego creates?
Oh man, the author doesn't pull any punches.
He states flat out that ego is at the root of almost every
conceivable problem and obstacle.

(06:31):
Every single one. That's a bold claim.
It is, but he argues it's responsible for everything from
not getting what we want to actually getting it and still
feeling strangely empty, you know?
Is this all there is feeling? Exactly, he writes.
The ego is the enemy of mastering a craft, of real
creative insight, of working well with others, of building
loyalty and support, of longevity, of repeating and

(06:54):
retaining your success, he argues.
It actually repulses advantages and opportunities and acts as a
magnet for enemies and errors. Quite the villain, isn't it?
Absolutely. And when you zoom out a bit,
it's truly a self-inflicted wound, isn't it?
The pioneering CEO Harold Jane once chillingly compared egoism
to alcoholism. Subtle, often unrecognized, and

(07:17):
utterly self-destructive. Wow, alcoholism.
That's intense. It is, he observed, that the
egotist does not stumble about knocking things off his desk.
He becomes more and more arrogant, and some people
mistake his arrogance for a sense of power and
self-confidence. Deceptive.
Very deceptive. It's a disease you might not
even realize you've contracted until it's way too late.

(07:38):
One of the early members of Alcoholics Anonymous had this
definition for ego that really resonates here, a conscious
separation from. There's a separation.
Yeah, a separation from reality,from others, from everything
that could actually lead to genuine success and fulfillment.
It prevents that direct, honest connection to the world around
us. Well, like trying to navigate a
dense fog with a blindfold on. That analogy of a self-inflicted

(07:59):
wound, of a fog, yeah, that's incredibly apartment.
So this entire deep dive then isstructured around how this ego
shows up in three main stages oflife, aspiration, success and
failure. The whole life cycle.
Right Holiday score message is both direct and stark.
Wherever you are, whatever you're doing, your worst enemy
already lives inside you. Your ego, he suggests.

(08:21):
We are the easiest person to fool.
And for anyone with ambition, ego isn't just a possibility, it
kind of comes with the territory.
Part of the package deal. It's the very thing that can
make us promising, yet simultaneously incredibly
vulnerable. So let's start by exploring how
ego sabotages us when we're justsetting out in that crucial
stage of aspiration. OK, let's do it.

(08:44):
All right, let's dive into Part 1.
Ego and aspiration, those sneakytraps that often trip us up when
we're just launching out into something new.
The first major one the book calls out is the Temptation to
Talk, talk, Talk. Ah.
Yes, the hype machine. We've all felt that urge,
haven't we? You get an exciting idea, you
share it with everyone, You soakin that initial applause and
encouragement, and then sometimes that's kind of where

(09:06):
the story ends. Right.
The actual doing never quite materializes.
It's an interesting phenomenon, isn't it?
How that initial burst of hype and chatter can inadvertently
replace genuine action. The book paints this really
vivid picture with the case of Upton Sinclair and his
gubernatorial bid in California.This story is wild.

(09:27):
It really is. Now imagine this.
Before he even had a realistic chance of winning the election,
he published a book titled I, Governor of California and How I
Ended Poverty. Wait before the election.
Before the election, detailing his brilliant policies as if
they were already accomplished. Fact.
He essentially wrote his victoryspeech before the race was even.

(09:48):
Run. I mean, that's and that's next
level pregaming, isn't it? Publishing your governorship
before you've even won it almostsounds like a comedy sketch.
It does, but as his friend the writer Kerry McWilliams pointed
out, Sinclair's vivid imagination of success actually
led him to lose interest in the real campaign.
Oh wow. He'd already acted out the part
mentally and that mental performance seemed to drain his

(10:08):
will to do the real gritty work of campaigning.
So the talk killed the walk. Pretty much.
He ended up losing by 1/4 of a million votes.
The book was a best seller, mindyou, but the campaign a crushing
failure. It's a stark reminder that talk
can very easily get so far aheadof action that it siphons off

(10:29):
the very energy needed for the real effort.
It's incredibly relatable though, isn't it?
It's far easier to talk about writing a novel, or to engage in
all the exciting peripheral stuff related to art and
literature. You know, the networking, the
brand building, the social media.
Oh yeah, the fun stuff. Right then, to actually commit
to the grueler, solitary act of creating the work itself, the

(10:52):
author gives the example of Emily Gould, a writer who landed
this Big 6 figure book deal. She then spent a year tumbling,
tweeting and scrolling instead of writing.
And her justification? She was building her brand.
Oof, that hits a little close tohome for anyone working online
today. Doesn't it?
It really makes you pause and consider.
Have you ever found yourself doing everything but the actual

(11:13):
work, convincing yourself that all those ancillary activities
somehow count? And modern tech with its
constant prompts, It doesn't make it any easier, does it?
Not at all. Facebook asks what's on your
mind. Twitter, compose a new tweet.
These blank spaces are constantly inviting us to
articulate what we plan to do toproject this positive image,

(11:35):
often masking the internal struggle or just the fear of
beginning. Right, the truth.
I'm scared, I'm struggling. I don't know how to start.
That's rarely what fills those spaces.
Exactly. The philosopher Sir in
Kierkegaard warned us about this, that expressing thoughts
too early can actually weaken the action by like, forestalling
it. Interesting.
We mistakenly think silence is asign of weakness, but as the

(11:58):
book illustrates, it's often a profound source of strength.
So what's the antidote then? How do we avoid this trap of
endless chatter? Well, the book offers some
timeless wisdom. General William Tecumseh
Sherman, a figure will definitely encounter again, had
this brilliant rule. He said never give reasons for
what you think or do until you must.
Maybe after a while a better reason will pop into your head.

(12:21):
Let it marinate. Exactly.
And then there's the incredible,almost mythical story of Bo
Jackson. He decided he was going to win
the Heisman Trophy and be taken first in the NFL draft.
A truly audacious goal. Insanely audacious.
And you know who he told about these grand ambitions?
Who? His coach?
His family. Absolutely no one except his

(12:43):
girlfriend. Get out.
Seriously. Seriously.
Wow. OK, that's a powerful lesson,
right? There it is.
The core insight is that talk depletes us.
Both talking and doing draw fromthe same well of energy and
commitment. And that makes sense in
scientific research, even back this up.
Visualizing progress can, for our brains, be mistaken for

(13:03):
actual progress, robbing us of the drive to execute.
We need to, as the saying goes, plug that hole in her face, that
constant urge to verbalize our intentions and seek external
validation. So silence is strength.
Silence in this context, becomesthe ultimate luxury.
It's the deliberate choice of the truly confident and the
strong. The most profound work.
The deepest insights often emerge from wrestling with the

(13:26):
void, facing the challenge head on instead of trying to talk it
away with noise. When those individuals do
eventually speak, their words carry the weight of earned
experience. OK, our next crucial trap in
this aspiration phase. The book frames it as a
fundamental choice to be or to do.

(13:47):
The eternal question. Right life, it argues,
constantly presents us with thisfork in the road.
Are you driven to pursue external validation, to be
somebody, to accumulate titles and recognition?
Or is your focus on making a tangible impact on trying to do
something meaningful regardless of the applause?
The book illustrates this so vividly with the story of the
legendary fighter pilot and strategist John Boyd, famously

(14:09):
known as 42nd Boyd for his uncanny ability to beat any
opponent in simulated air combatin under that time. 40 seconds.
That's isn't. It Boyd was this quiet force at
the Pentagon, never seeking the limelight, no bases named after
him, retired to a small apartment.
Yet his influence on military strategy was absolutely

(14:31):
monumental. So he wasn't about the being.
Not at all. He had his powerful, almost
ritualistic speech he would giveto his proteges.
Tiger, one day you will come to a fork in the road.
OK, if you go that way, you can be somebody, a general and
Admiral, a big shot. But if you decide you want to do
something to actually make a difference, your work might

(14:52):
matter. Wow, that's that's truly
compelling. It makes you reflect how many of
us have stood at that exact crossroads, maybe without even
fully realizing it was a choice between being and doing.
We often get mesmerized by the outward trappings of success,
don't we? Totally.
The impressive job titles, the number of assistants, the
coveted parking spots, the grants, the access to VIP's, the
size of the paycheck. All the shiny objects.

(15:14):
Right. We mistakenly equate these
symbols with genuine accomplishment.
As the author puts it so directly, having authority is
not the same as being an authority.
Impressing people is utterly different from being truly
impressive. Exactly.
Boyd himself had another powerful teaching tool.
He would write duty honor country on a chalkboard.

(15:35):
OK, then dramatically cross themout and replace them with pride,
power, greed. Whoa.
He was illustrating how ego can suddenly corrupt our original
values, how the systems designedto serve a greater purpose can
paradoxically derail us into self-interest.
The choice he presented to his students fundamentally boiled

(15:56):
down to purpose. What drives you?
So it all comes back to purpose,yeah.
If your deepest purpose is merely to be recognized, to be
included, or just to make your own life easier, then you'll
find yourself constantly seekingattention, chasing titles,
telling people what they want tohear.
So what's the core message you can really extract?
Here the author quotes the greatFrederick Douglass.
A man is worked upon by what he works on, What you choose to

(16:19):
dedicate your time and energy to, what you choose to do for
money, it fundamentally shapes you.
If your purpose is genuinely larger than yourself, to
accomplish something significant, to prove something
to yourself, then suddenly everydecision becomes both simpler
and more challenging. Simpler and harder?
How so? Simpler because the distractions

(16:40):
fade away, but harder because every single opportunity has to
be rigorously evaluated. Does this truly help me achieve
what I've set out to do? Am I choosing this out of
selflessness or selfishness? It is, without a doubt, the
harder path. Boyd's choices, for instance.
They weren't without cost. He was known, maybe
affectionately, maybe not, as the ghetto Colonel, for his

(17:01):
frugal lifestyle. Ghetto.
Girl. Yeah, and he famously died with
uncashed expense checks, viewingthem as kind of like bribes.
Wow, principal over pennies. Absolutely.
He was often passed over for promotions, are largely
sidelined by the military establishment, almost as a
punishment for the work he pursued.
Yet his influence on military strategy, his impact on

(17:21):
individuals, immeasurable. His story teaches us that
chasing external prizes or fame often isn't the pathway to real,
lasting impact. It forces us to ask ourselves,
doesn't it? Are you truly ready to make the
right decision, or do those shimmering prizes still glitter
too brightly in the distance? That's the $1,000,000 question
right there. Moving on, our third critical

(17:43):
trap in the aspiration phase andarguably one of the most vital
for long term success, is about embodying the mindset of become
a student. Always be learning.
Exactly. The book argues eloquently that
true mastery is an ongoing journey.
It demands perpetual learning, profound humility, and
relentless self-assessment. There's never a point where you

(18:03):
are truly done. It really makes you wonder, when
exactly does the learning stop? And the book's answer is a
resounding never. Never.
Ever. Never, ever.
And it provides this incredible anecdote about Kirk Hammett of
Metallica. Oh yeah, the guitarist, right.
Think about it. Early 1980s he was practically
plucked from obscurity, brought into Metallica, a band quite

(18:24):
literally destined to go places.This was just days before his
very first show with them. They were on the absolute
precipice of becoming one of thebiggest bands in the world.
That's insane pressure. Totally on their way to selling
millions upon millions of albums.
So can you even wrap your head around that?
You're at the very threshold of rock stardom, about to hit it

(18:44):
big, and your immediate thought isn't about fame or money or
groupies, but about taking guitar lessons.
Wait, lessons? He was already in Metallica.
Exactly. He was already a phenomenal
guitarist, but he immediately sought out Joe Satriani as his
teacher and continued those lessons for two solid years.
What a counterintuitive move. Right.

(19:04):
That speaks volumes about a truedesire for mastery, not just
fame. Satriani himself noted that
Hammett was already shredding, had a great right hand, but he
didn't learn how to play an environment where he learned all
the names and how to connect everything together.
The theory and structure. Precisely.
Santriani's teaching system was rigorous weekly lessons Learn

(19:24):
the material or don't bother coming back.
Hammett endured this harsh, objective feedback, drilling
fundamentals and musical theory for two years.
This deliberate process of deferring to the master of
subsuming his ego was absolutelycritical.
Because the ego would say I'm already in Metallica.
Exactly. The book highlights that the

(19:45):
pretense of knowledge is our most dangerous vice precisely
because it actively prevents us from truly getting better.
And this principle isn't just for musicians, right?
Not at all. Frank Shamrock, the mixed
martial arts pioneer, had this brilliant training philosophy he
called plus, minus and equal. Plus minus equal.
Yeah, to achieve greatness, a fighter, he argued, needs

(20:06):
someone better. A+ to learn from someone lesser,
a minus to teach which actually solidifies your own
understanding. Oh, interesting.
Teaching reinforces learning. Right.
And someone equal to challenge yourself against.
It's this continuous dynamic cycle of growth ensuring you
never plateau. That's a great framework.
So what's the big threat here then?
The great threat is what the book aptly labels the I've Made

(20:29):
It Syndrome. Complacency.
Exactly. Ego, that cunning internal
voice, whispers that you're donelearning, especially after some
early success. It tells you you've arrived.
They picked you because you already have what it takes.
What a dangerous trap. It is.
Had Hammett fallen for that, he'd likely be forgotten today.
Just another talented guitarist from a band that fizzled out.

(20:53):
Humility is that invisible forcethat keeps us in what the author
calls long periods of obscurity,wrestling with difficult
problems, accepting that we don't know enough, and
committing to continuous study. It's the difference between the
amateur and the pro. Absolutely.
The amateur becomes defensive when challenged.
The true professional finds joy in learning, even in being shown

(21:13):
up, because they understand it'sall part of the journey to
becoming better. Okay, our final insight in this
aspiration phase is all about the profound power of restrain
yourself. This one, this one truly
resonated with. Me.
Yeah. How so?
It illustrates how pursuing truly great goals sometimes
demands an almost superhuman ability to endure in dignity and

(21:36):
suppress explosive anger, no matter how justified that anger
might feel in the moment. You'd be hard pressed to find a
better example of this than Jackie Robinson.
Absolutely icon. If you knew him as a young man,
you certainly wouldn't have predicted he'd become the figure
who broke baseball's color barrier.
He ran with a gang, openly challenged authority.
He wasn't naturally passive. Not at all.

(21:57):
He was even arrested for arguingwith police.
He was fiery and assertive. OK, so this is where the story
gets truly compelling. When Branch Rickey, the manager
of the Brooklyn Dodgers, was scouting Jackie, he had one
pivotal question. It wasn't about his talent,
which was undeniable. What was it?
It was, do you have the guts? Not the guts to fight, but to

(22:18):
not fight back. Wow.
That's A twist. Ricky famously play acted the
racial abuse Robinson would face.
Hotel clerks refusing rooms, rude waiters, opponents
screaming slurs, deliberately spiking him.
Robinson, despite his own passionate nature, assured him
he was ready. He had been arrested for arguing
with Palouse as a young man, yethe consciously chose to tolerate

(22:40):
unimaginable abuse for a far greater cause.
It's an astonishing contrast, isn't it?
Robinson was hit by over 72 itches.
Layers frequently aimed their spikes right at his Achilles
tendon, trying to injure him. 72, yeah.
Yet he held firm to his unwritten pack with Ricky.
Now compare. This is someone like Ted
Williams, a white player, 1 of baseball's all time greats.

(23:02):
He notoriously spit at fans in 1956 and later Bo said he'd do
it again. Seriously.
Yeah, for a black player like Robinson, that kind of behavior
would have been career ending. He would have set back the
entire grand experiment, as Ricky called it, for a
generation. His self-control wasn't just
admirable, it was absolutely essential.
So his restraint was strategic. Absolutely strategic.

(23:24):
The book reminds us of this by quoting the fighter boss Rutten,
who writes Rustig, which means relax on his hands before
fights. Practical reminder.
Yeah, understanding that anger is often a recipe for tactical
failure. As John Steinbeck observed, we
often lose temper as a refuge from despair.
Ego, the book says, is the absolute opposite of what is

(23:44):
needed in these high stakes, challenging scenarios.
So what's the profound take awayhere for us?
The author lays it bare. Slights, dismissals, little
fuck. Use one sided compromises,
you'll get yelled at. We've all been there.
Right. You'll want to fight back.
You'll want to say I am better than this.
I deserve more. What a deeply human, infuriating
feeling that is. We all feel that impulse.

(24:06):
Do you know who I am? Oh yeah, the ego flares right
up. But in these crucial early
stages, especially when you're building something, the book
insists you must do nothing. Take it, eat it until you're
sick, endure it quietly brush itoff and simply work harder.
It's about playing the long game.
It's a timeless reality, unfortunately, that those who
are up and coming must often endure the abuses of the

(24:26):
entrenched. You simply cannot change the
system until you've made it, so to speak.
You have to earn that right? In a way, yeah.
Robinson, at 28, had already paid plenty of dues in the Negro
Leagues, but he was forced to doit all again, accepting new
indignities in the majors. It's about strategic patience,
finding a way to make the situation, even a terrible one,

(24:47):
suit your larger purposes. Even if that purpose is just
buying extra time to develop your skills, to learn from
others on their dime, to quietlybuild your base.
And he did eventually push back.He did, but it wasn't until he
had proven himself unequivocallywinning Rookie of the Year and
then MVP that he began to asserthis boundaries more firmly.
Not before he had a temper like any of us, but he learned early

(25:11):
that the precarious, tight ropy walk would tolerate only
restraint and had zero forgiveness for the indulgence
of ego. All right, we've navigated the
often treacherous waters of aspiration.
Now let's move on to Part 2. Ego in success?
The summit, or what? Seems like it, right?
This is where things get truly intriguing, because you'd

(25:31):
naturally assume that once you've made it, once you've
achieved your goals, the battle against ego is over.
You won. If only were that simple.
Exactly. But Holiday reveals how success
itself brings new, often more insidious temptations.
Our first cautionary tale here is the almost unbelievable saga
of Howard Hughes. Howard Hughes the ultimate

(25:55):
cautionary tale. Perhaps what's truly astonishing
about his story is how he servesas this ultimate public warning.
Here's a man who inherited 3/4 of his father's immensely
profitable tool company at just 18 years old, made worth nearly
$1,000,000, a staggering sum back then.
Wow, 18. Yeah, And in what the book
describes as an act of almost incomprehensible foresight, he

(26:17):
systematically bought out his relatives to gain full control,
leveraging both his personal assets and company funds.
This very business would go on to generate billions over the
next century. OK, so far so good.
Visionary, even. Right, but this is where the air
to shift dramatically. Here comes.
We often romanticize figures like Howard Hughes.
You know, the eccentric billionaire, the visionary
pioneer. But the book paints a far

(26:40):
different picture, describing his years at the helm as a
deranged crime spree more than acapitalistic enterprise.
A crime spree? Seriously.
That's the author's phrasing. He was without a doubt a gifted
mechanical genius and a brave pilot, yet his ego, completely
unchecked, evaporated hundreds of millions of dollars and

(27:00):
ultimately led to this miserable, pathetic end almost
exclusively due to his own actions.
Not like unforeseen market forces or bad luck.
So it was self sabotage on a grand scale.
Grand scale is right. The paradox is utterly stark.
He virtually abandoned his father's thriving company, just
siphoning cash to move to Hollywood and become a film
producer. He lost over $8 million in stock

(27:21):
before the Great Depression evenhit.
His most famous movie, Bell's Angels, took three years, lost
$1.5 million, and nearly bankrupted the very tool company
he inherited. Then he lost another $4 million
on Chrysler stock. His defense contractor, Hughes
Aircraft, despite his personal inventiveness, was a consistent
failure. The infinite Spruce Goose.
Oh yeah, the giant wooden planes.

(27:43):
That cost $20 million, flew oncefor barely a mile and then sat
in an air conditioned hangar fordecades at 1,000,000 bucks a
year in upkeep. A million a year just to store
it? Yep.
He ran the RKO movie studio intothe ground, losing $22 million
slashing employees from 2000 to fewer than 500.
Ironically, the book notes, his occasional absence from his

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businesses often allowed them tothrive.
Wow, so his presence was toxic to the bottom line?
Largely, yes. So what's the painful core
lesson for us here? The author writes Howard Hughes,
like so many wealthy people, died in an asylum of his own
making. He felt little joy.
He enjoyed almost nothing of what he had.
What a brutal, sobering truth. His biographers paint this

(28:26):
haunting scene of him like nakedin his white chair, unwashed,
dictating these irrational memosabout Kleenex one minute and
then, in flashes of his former brilliance, strategically
outlining how to outrun creditors the next.
They chillingly observed, It waslike IBM had deliberately
established a pair of subsidiaries, one to produce
computers and profits, another to manufacture Edsels and

(28:48):
losses. This image of Hughes isn't just
a historical footnote, it's a living, breathing metaphor for
ego's destructive power. It truly is his unchecked ego,
tragically exacerbated by injuries and addition.
It just ultimately consumed him.It brings to mind Aristotle's
observation that without virtue and training, it is hard to bear

(29:08):
the results of good fortune suitably.
Yeah, fortune needs virtue. Hugh serves as this very public,
highly visible example of how ego, like a corrosive acid, can
utterly wreck a life, turning immense success into profound
misery. His story is a powerful, almost
desperate reminder that success is intoxicating, yet to sustain
it requires sobriety. It's about clear headed

(29:30):
self-awareness when the world wants to shower you with praise
and tell you you're infallible. OK, our next significant pitfall
in success, and one that trips up countless individuals, is the
danger of don't tell yourself a story.
The narrative trap. Exactly.
It's incredibly tempting, after achieving something significant,
to construct this false narrative of your own genius or,

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you know, preordained success, rather than remaining focused on
consistent, diligent execution. Bill Watch, the legendary coach
who took the San Francisco 49ersfrom being one of the worst
teams in football to Super Bowl champions in just three years.
An amazing turn around. He's the quintessential example
here. It would have been incredibly

(30:11):
easy, even expected, for him to embrace the genius label to
claim he had it all planned out from day one, but he explicitly
refused. When asked if he had a timetable
for winning the Super Bowl, his answer was consistently no.
Let's dig into that for a moment.
Walsh's team went a dismal 2 and14 in his first season after
making massive changes. 2 and 14.

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Ouch, right? He even considered resigning
midway through his second year, yet he somehow built a dynasty.
What was his actual secret? It wasn't some grand sweeping
vision or prophetic narrative. So what was it?
He simply implemented what he called his standard of
performance, meticulously detailing what needed to be
done, when and how, down to the most seemingly trivial level.

(30:54):
Like what kind of details? We're talking things like
players not sitting on the practice field, coaches wearing
ties, precise drilling during practice, ensuring the locker
rooms were spotless, tiny things.
OK, that sounds almost obsessive.
Maybe, but it wasn't micromanaging in the negative
sense. It was about instilling this
culture of absolute excellence. Walsh intuitively understood

(31:17):
that if his players rigorously adhered to these minute details,
then, as he famously put it, thescore takes care of itself.
Focus on the process, not the outcome.
Exactly, the winning would be a natural by product.
He was humble enough to recognize that the rapid pace of
their success was partly A fortuitous break of the game,
not solely due to some pre planned brilliant strategy he

(31:39):
can talk to. He acknowledged the luck
involved. He did.
He even fired a coach who complained Walsh was too caught
up in minutia and didn't have big enough goals to win because
that coach completely missed thepoint of the standard.
Wow, he stuck to his guns. So what's the real take away
here for us? The author defines narrative as
when you look back at an improbable path to success and

(31:59):
say I knew it all along. The revisionist history.
Right. It begs the question, how
incredibly tempting is it for you to retroactively craft such
a perfect, coherent story for your own successes?
We all want to believe we're brilliant strategist, not just
diligent people who worked hard and maybe got a few good breaks.
It's a powerful human impulse, absolutely.

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But as author Tobias Wolf poignantly writes, these
explanations and stories get cobbled together later, and
after the stories have been repeated, they put on the badge
of memory and block all of the roads of exploration.
Wow. Block all other routes of
exploration. That's deep.
It is These convenient narratives don't just
reinterpret the past. They can profoundly impact our

(32:41):
future. The 49ers themselves proved this
point. In the two seasons immediately
following their first Super Bowlwin, they experienced this
terrible slump, losing 12 of 22 games.
Why? What happened?
Because players prematurely credited themselves with powers
and slacked off, assuming success was now guaranteed, they
forgot the standard. They bought into their own hype.

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Exactly. They only returned to dominance
after recommitting to Walsh's rigorous standards.
Innovators like Jeff Bezos and Paul Graham often caution
against starting with grand, sweeping visions.
Instead, they advocate for starting deceptively small and
iteratively scaling ambitions. Keep your identity small.
Keep your identity small. Yeah, that's key, because it

(33:25):
prevents you from believing yourown legend before it's even
written. Next up, the critical question,
What's important to you? The book highlights how success
can subtly lead us astray, making us lose sight of our core
priorities and instead chase what others have rather than
what genuinely matters for our own fulfillment.
It's a surprisingly common trap.We see this played out so

(33:45):
clearly in the post Civil War lives of two giants, Ulysses S
Grant and William Tecumseh Sherman.
OK, two massive historical figures.
Right. These two men were the dual
architects of the Union's hard won victory, achieving hero
status and virtually anything they desired from a grateful
nation. Sherman, after the war chose to

(34:06):
retire to New York City, findingwhat he described as happiness
and contentment. He famously declared.
I have all the rank I want, justcontent with his
accomplishments. OK, so Sherman found peace.
What about Grant? This is where the story takes a
fascinating turn. 2 heroes, 2 masterminds of victory, each
given their pick of paths forward.

(34:27):
One found contentment and peace.And the other.
The other found misery and public scorn.
Grant, despite having no prior political interest, allowed
himself to be swept into the presidency and presided over one
of the most corrupt, contentious, and least effective
administrations in American history.
Pretty bad. He left office maligned,
genuinely surprised by how poorly it had gone, and

(34:49):
tragically, later in life he lost almost every penny in a
devastating Ponzi scheme. Oh no, that's heartbreaking.
So why the different paths? Sherman keenly observed that
Grant, despite his immense military accomplishments, aimed
to rival the millionaires who would have given their all to
have won any of his battles. So he started comparing himself.
Exactly. He had achieved so much, yet it

(35:11):
felt insufficient. This is ego swaying us,
compelling us to want more than everyone else, to say yes to
things out of vague attraction or out of greed or vanity, even
when, as the book points out, strategies are often mutually
exclusive. You can't have it all.
You can't be a world renowned opera singer and a teen Pop Idol

(35:31):
simultaneously. Life demands trade-offs, but ego
and it's insatiable. Hunger rejects these trade-offs.
It wants it all. So what's the vital take away
from this comparison? The author articulates it
chillingly. The farther you travel down that
path of accomplishment, the moreoften you meet other successful
people who make you feel insignificant.
Oof, that's a vicious cycle. Isn't it?

(35:54):
What a truly vicious, never ending cycle.
No matter how incredibly well you're doing, there will always
be someone else whose achievements, whose wealth,
whose fame, or whose perceived happiness can make your own feel
utterly insignificant. And that's a cycle that
continues ad infinitum. While our time on Earth
certainly does not. It forces us to ask a crucial

(36:15):
question. What truly, fundamentally is
important to you? Got to define your own enough.
Precisely. Is it financial security, your
family influencing others, or fulfilling a specific purpose?
All are valid. But you absolutely need to know.
And then you need the courage and clarity to say no to
distractions, to stupid races that don't matter, to

(36:36):
opportunities that don't align with your deepest values.
Ego wants you to say yes to everything.
Ego demanding everything tells you to cheat even if you love
your spouse because it wants what you have and what you don't
have. Only when you understand your
true purpose can you develop that quiet confidence and fierce
independence needed to resist the endless allure of more.
Another critical facet of navigating success is the

(36:57):
imperative of managing yourself.The leader's burden.
Right. The strategies, systems, and
habits that propelled you to thetop might not be sufficient or
even appropriate to sustain you there.
Effective leadership, the book argues, demands order,
discipline, delegation, and, perhaps most importantly, the
ability to manage your own impulses and ego.

(37:19):
This is beautifully illuminated by contrasting the leadership
styles of Dwight D Eisenhower and John DeLorean.
OK. Ike versus the car guy.
Pretty much. When Eisenhower, having just
returned from his inaugural parade, stepped into the Oval
Office for the first time as president, his chief usher
handed him two sealed envelopes marked confidential and secret.
OK, what did he do? Eisenhower's immediate, decisive

(37:42):
reaction was Never bring me a field envelope.
That's what I have a staff for. Wow, straight off the bat, let's
dig into that for a moment. Eisenhower, arguably the most
powerful man in the world at that time, made it his first
priority to not do everything himself.
Delegation for minute 1. His initial focus as president
was organizing the executive branch into a smooth,
functioning and order driven unit.

(38:03):
He understood the power of effective delegation and the
necessity of trusting his staff.As his chief of staff famously
put it, the president does the most important things, I do the
next most important things. Julia rolls clear priorities.
Eisenhower understood that urgent and important were not
synonyms and kept his focus firmly on the big picture.

(38:23):
OK, so that's Ike. No.
Contrast that with John de Lorean.
Right, the De Lorean car creator.
After dramatically walking away from General Motors to create
his own futuristic car company, he deliberately, almost
defiantly, flouted conventional business practices.
He was convinced that order, discipline and establish
processes stifled creativity. So chaos equals creativity.

(38:46):
That seemed to be his theory. The result?
A dysfunctional and even corruptorganization that ultimately
imploded into criminality and fraud, losing some $250 million.
Court of a billion dollars. Yeah, DeLorean worked
constantly. But as one executive observed,
he was chasing colored balloons,constantly distracted, incapable
of delegating except to sycophants, and often bending

(39:08):
the truth to suit his narrative.His rampant ego was the
undeniable root of the problem. So what's the crucial take away?
For us? It's fascinating how those
small, fun, endlessly engaging and flattering things like
putting out fires or being involved in every tiny detail
can distract us from the strategic big picture, which is
often much harder to discern. If you don't think about the big

(39:31):
picture, sure, who will? Exactly.
Your responsibilities shift fundamentally from doing the
work to deciding and managing it.
This requires A profound humility to accept that others
may be more qualified in certainareas and that your time is far
better spent on higher level strategic tasks.
Micromanagers, as the bitcoins out are often egotists.

(39:51):
They can't effectively manage others and as a result they
quickly become overloaded and ineffective.
Makes sense in charismatic visionaries.
They often lose interest in the messy details of execution.
Once the initial excitement wears off, leaving a wake of
unfulfilled promises, the book delivers a potent warning.
A fish stinks from the head, is the saying.
Well, you're the head now. Responsibility.

(40:14):
You simply must learn how to manage yourself, and then how to
truly manage others before your industry or your own enterprise
devours you whole. This means setting clear top
level goals, rigorously enforcing them, and focusing on
results, not the flattering illusion of being indispensable
in every tiny detail. OK, our fifth crucial point in

(40:34):
navigating the success phase is a sharp warning.
Beware the disease of me. Ah, the team killer.
Exactly. The book argues that success,
paradoxically, can breed self-interest and internal
conflict, fundamentally undermining collective goals and
the cohesion of a team. To illustrate this, the book
draws A compelling contrast between the often squabbling

(40:54):
Allied generals World War 2 and the singular example of George
Catlett, Marshall Junior. George C Marshall, big name.
Huge. While other generals frequently
protected their turf, lobbied intensely for promotions, and
eagerly shaped their own place in history, Marshall was
strikingly different. His behavior was virtually
devoid of such ego driven actions.

(41:15):
This is where Marshall's story truly becomes inspiring.
Pat Riley, the legendary basketball coach, developed this
powerful concept he calls the Innocent Climb.
Oh yeah, I know this one. That period where a team works
together selflessly, driven onlyby the shared goal of winning.
But after success hits, after the media attention and
accolades, the bonds often fray and individual egos start to

(41:38):
appear. This, Riley says, is the disease
of me. We see it all the time in
sports. Totally.
Think of examples like Shaq and Kobe.
They're immense talents, ultimately clashing, unable to
play together harmoniously. Or Michael Jordan, whose
competitive fire sometimes led him to punch his own teammates.
Intense. Or the Enron employees plunging
California Into Darkness for personal profit.

(41:59):
Marshall, in stark contrast, stands out for never seeking
personal glory, often allowing others to take credit or receive
honors. What was his secret to such
unwavering selflessness? Marshalls profound sense of
honor meant turning down honors.Turning down honors.
He actively discouraged lobbyingfor promotions and even asked

(42:19):
people to stop pushing for him to be chief of staff because he
felt it made him too conspicuous.
In a truly astonishing act of humility and duty, he turned
down the command of D-Day, the largest coordinated invasion in
history, a role that then went to Eisenhower.
He turned on D-Day commands. He simply told President
Roosevelt, my wishes have nothing to do with the matter.

(42:41):
Ego demands immediate validationand accolades, but true
confidence, as the book highlights, is able to wait and
focus on the task at hand, regardless of external
recognition. Confidence can wait.
Ego needs it now. Exactly.
It's a core principle that we never earn the right to be
greedy or to pursue our own interests at everyone else's
expense. So what's the larger lesson for

(43:02):
us? Here, the author quotes Cheryl
Strayed. You're becoming who you are
going to be, and so you might aswell not be an asshole.
Blunt but true. Success, if we're not careful,
can turn us into someone we never intended to be.
Marshall, for instance, refused to exact revenge on a general
who had previously banished him to obscure postings simply

(43:23):
because he recognized that the man was still useful to the
country's war effort. That's true magnanimity.
President Truman famously observed that.
Never did General Marshall thinkabout himself.
He didn't care about managing his public image or gazing at
his own portrait. Play for the name on the front.
Exactly as soccer coach Tony Adams wisely advised, play for

(43:43):
the name on the front of the jersey and they'll remember the
name on the back. Marshall's selflessness and
unwavering integrity were not weaknesses.
They were the bedrock of his immense strength and lasting
impact. While his name might not be as
widely known today as some, everyone lives in a world he was
largely responsible for shaping.And the credit?
Who cares, so long as the work gets done?

(44:04):
Our 6th and perhaps most philosophical stabilizer in the
face of success is to meditate on the immensity.
Getting cosmic now. A little bit.
This is a truly profound idea that connecting to something
vastly larger than oneself, whether it's the cosmos, the
sweep of history, or the raw power of nature, is an
incredibly powerful antidote to ego's relentless self

(44:27):
centeredness. The book shares the deep
experience of John Muir, the renowned preservationist and
explorer. In 1879, while exploring
Alaska's formidable Glacier Bay,he was overwhelmed by this
feeling he called sympathea. Sympathea.
Yeah, profound, almost spiritualconnectedness with the cosmos,
an oceanic feeling. He meticulously documented in

(44:48):
his journal his realization of being an infinitesimal point in
the immensity, observing the entire ecosystem functioning in
perfect harmonious sync, a vast machine he was merely a tiny
part of. Let's dig into that imagery.
When we're successful, ego oftentells us that meaning springs
from our activity, from being the absolute center of
attention, from feeling powerfuland wealthy.
It whispers that that's what makes this important.

(45:10):
The center of the universe complex.
Right. But what if, as mere discovered
true meaning and perspective come from realizing just how
incredibly small you are in the grand scheme of things?
Ego, in its relentless focus on self, actively blocks this
connection to beauty, to history, to the grand sweep of
time, leading instead to feelings of emptiness and a

(45:32):
relentless sensation of being ona never ending treadmill.
No wonder success could feel hollow sometimes.
Exactly. We lose touch with the very
cosmic energy that once fueled our initial aspirations.
It's quite sad how disconnected we've become from the vastness
of both the past and the future.We often forget, for instance,
that woolly mammoths were still roaming the earth while the

(45:53):
pyramids were being built. No way, Really.
Yep. Or that Cleopatra lived closer
to our time than to the actual construction of those same
pyramids? Mind blown.
And here's another mind Bender. There's a chain of just six
handshakes that could connect Barack Obama all the way back to
George Washington. OK, that's wild. 6° of
separation to the founders. Right.
It's so easy to slip into the assumption that our own times

(46:16):
are blessed, unprecedented, or uniquely important.
The author even reminds us that photos from 50 years ago are in
black and white, but their sky was the very same color as ours.
That's a great point. We are fundamentally no
different from those who came before us, and we never truly
will be. It's difficult to maintain
humility when you're as outwardly grand as Muhammad Ali

(46:38):
proclaimed himself. But that's precisely why truly
great people have to work even harder to fight against this
natural human headwind. It's incredibly difficult to be
self absorbed and convinced of your own singular great when
you're in the profound solitude of a sensory deprivation tank,
or walking along a vast beach atnight with an endless black

(46:58):
ocean crashing beside you, stretching to Infinity.
Takes you out of yourself. Completely.
And that prompts A vital question.
Why do so many great leaders, thinkers and artists
deliberately go out into the wilderness and return with fresh
inspiration? Because in those vast, quiet
spaces, they find perspective. They reset.
They managed to silence the incessant noise of their own

(47:19):
thoughts and the world's demands, allowing themselves to
hear that quiet, often ignored internal voice they truly need
to listen to. This profound perspective makes
ego feel impossible, forcing a deep and abiding humility.
It helps us end your conscious separation from the world, to
reconcile ourselves with the larger realities of life, and to

(47:40):
truly grasp how much came beforeus and how much will continue
long after. Finally, in the success phase,
the book offers a vital piece ofadvice.
Maintain your sobriety. And not just the literal kind.
Exactly. This isn't just about abstaining
from substances. It's about clear headedness,
unwavering modesty, and the steady application of reason as
essential stabilizers against egos.

(48:01):
Intoxicating effect, especially when granted power and position.
Angela Merkel, the former chancellor of Germany, is
presented as the very antithesisof nearly every assumption we
make about a head of state. How she's known for her
plainness, her profound found modesty, her complete
disinterest in flash or fiery rhetoric.
She's quiet, reserved and notably sober in her approach,

(48:23):
while there are too many leadersseem utterly intoxicated by
their own ego and the allure of power.
This is where her story truly stands out.
In a world clamoring for loud, charismatic leaders, Merkel
embodies Aesop's tortoise slow, steady and ultimately
victorious. Slow and steady wins the race.
There's a wonderful anecdote from her childhood swimming

(48:45):
lessons. As a young girl, she would stand
on the diving board for minutes on end just thinking.
Just thinking. Yeah, until the bell for the end
of the lesson finally rang, and then she would jump.
She was making a deliberate, calculated decision, not rushing
into anything. She famously declared Beer is a
bad advisor. Wise words.
When the Berlin Wall fell, she was 35, had one beer, went to

(49:06):
bed and showed up early for workthe next day.
It was a diligent plotting path that led her to become
chancellor in her 50s. Her background as a physicist
undoubtedly contributed to her rational, objective approach.
She consistently made decisions about the situation at hand,
never about herself. What's truly compelling here is
how her unpretentiousness becameMerkel's most potent weapon.

(49:29):
How did she use it? She didn't flinch when Putin,
seeking to intimidate her, brought his large hunting dog
into their meeting. She later calmly joked about it,
subtly making him look foolish. The book reinforces the timeless
idea of Sir Tu Patrol de Zell. Above all, not too much zeal.
Right. A French proverb meaning that
too much passion or zeal can actually lead to recklessness

(49:52):
and poor judgement. Leaders like NFL coach Bill
Belichick and Merkel understand that stake is what wins games
and moves nations forward. Sizzle, on the other hand, makes
it harder to make the right decisions.
Stake over sizzle. I like it.
So what's the profound implication here?
The author writes. As hard as it might be to
believe from what we see in the media, there actually are some
successful people with modest apartments.

(50:13):
Imagine that. Most successful people are
people you've never heard of. They want it that way.
What a powerful, almost countercultural challenge to our
ingrained assumptions about whatsuccess looks like.
They choose to live modest private lives, actively
preferring anonymity. And that, ultimately, is what
keeps them sober, clear headed and effective.

(50:33):
It helps them focus relentlesslyon their actual jobs rather than
the performance of their jobs for public consumption.
It's a powerful lesson that genuine, lasting success doesn't
always come with public glamour or excessive self promotion.
It's about being effective, impactful and clear minded, not
merely famous or adorned with flashy titles.
We've journeyed through the stages of aspiration and

(50:55):
success. Now we arrive at the third stage
of life, one that every single person inevitably encounters
failure. The Valley.
This is often where ego can be at its most destructive, turning
temporary setbacks into permanent wreckage.
But it can also be the ultimate Crucible for profound
reorientation and growth. Our first concept for this phase
is a lifetime or dead time. Interesting framing.

(51:18):
This core idea suggests that every single moment of failure
or set back presents us with a fundamental choice.
You can either passively wait for the storm to pass wallowing.
Or you can actively utilize thattime for learning, growth, and
preparation. Exactly.
The book provides a truly transformative story in the life
of Malcolm X. Before he became the powerful

(51:40):
orator and human rights activistwe know today, he was a criminal
known as Detroit Redhead, a numbers runner, drug dealer,
pimp and armed robber. A rough start.
Very rough. He was eventually arrested for
fencing a stolen watch and carrying a gun, receiving a
lengthy 10 year prison sentence.Let's truly reflect on that for
a moment. When your own actions land you

(52:01):
in prison for a decade, that's an undeniable failure, a
complete collapse of your current life path.
Absolutely rock bottom. But what's astonishing about
Malcolm X's story is how he literally transformed his prison
cell into a personal college. He chose a live time.
How did he do that? He taught himself to read by
painstakingly copying the entiredictionary, word for word,

(52:23):
devouring books on history, sociology, philosophy, he
famously said. From then until I left that
prison, in every free moment I had, if I was not reading in the
library, I was reading in my bunk.
Wow, total dedication. And he felt, remarkably, never
so truly free. Free in prison.
That's profound. This incredible transformation

(52:43):
is a perfect illustration of Robert Greene's lifetime or dead
time concept. Malcolm X's profound shift was
powered by this unique mix of acceptance, humility and
strength. And his story isn't unique in
history, is it? Not at all.
Francis Scott Key penned the Star Spangled Banner while
literally trapped in a British ship during the War of 1812.

(53:03):
Victor Frankel, the renowned psychiatrist, refined his
profound psychologies of meaningand suffering while imprisoned
in Nazi concentration camps. Finding meaning and suffering.
Ian Fleming, confined to bed rest, wrote Chitty Chit Bang
Bang by hand. Walt Disney decided to become a
cartoonist while laid up after stepping on a rusty nail.
These individuals didn't let their setbacks to find them.

(53:24):
They use them as springboards. It's so tempting, though, when
injustice strikes, to indulge inanger, grievance or deep
depression. It feels good, almost righteous,
to wallow. You can feel validating, sure.
But, the author says bluntly, this is short sighted.
So many people fail not because of the initial set back, but
because they reinvest energy into exactly the patterns of

(53:46):
behavior that caused our problems to begin with.
Repeating the cycle. They distract themselves, they
plot revenge, or they simply refuse to acknowledge their own
role in their misfortune. It forces us to confront a
really uncomfortable but important question.
What if instead of wallowing, weasked ourselves, is this an
opportunity for me? Can I use this for my own

(54:07):
purposes? I will not allow this to be dead
time for me. Flipping the script.
Exactly. Booker T Washington's timeless
advice, Cast Down Your bucket where you are, resonates deeply
here. It encourages us to make
resourceful use of what's immediately available to us,
rather than letting stubbornnessor a sense of victimhood make an
already bad situation exponentially worse.

(54:28):
The real dead time was often when we were blindly controlled
by ego chasing external validation.
Now, in the face of failure, we have the profound chance to
truly live, to learn, and to adapt.
Our next crucial lesson in the realm of failure is that the
effort is enough. Letting go of results, that's
tough. It is this principle liberates

(54:49):
us to focus solely on doing the right thing, on fulfilling our
own deeply held personal standards, regardless of whether
external validation or reward ever materializes.
The book introduces us to the largely unsung hero of history,
General Belisarius. Described as one of the greatest
yet unknown generals, He consistently won brilliant
battles for a paranoid and ungrateful Emperor Justinian.

(55:12):
And what was his reward? Promotion.
Suspicion, humiliation and ultimately, according to legend,
poverty and blindness. His personal historian was even
corrupted to intentionally tarnish his image.
Oh, that's brutal. What's truly astonishing about
Belisarius is that despite this egregious injustice and lack of
recognition, he never complained.

(55:32):
Never complained. How is it possible?
He just did his job, which he genuinely believed was his
sacred duty. He knew deep down that he had
performed exceptionally, that hehad done what was right and
honorable, and that, for him, was enough.
What an incredible, almost unbelievable example of Stoicism
in the face of profound, undeserved suffering.

(55:53):
His absolute lack of complaint, even in private letters, is
truly remarkable. Ego, on the other hand,
perpetually demands full appreciation.
It leads to soul crushing disappointment when our hard
work isn't recognized or rewarded in the way we think it
deserves. So where's my trophy mentality?
Right. This is a dangerous attitude,
the book explains, because when someone works on a project, it

(56:15):
leaves their hands and enters the realm of the world.
It stops being something he controls.
We have, let's be honest, minimal control over external
rewards like validation, recognition or fame.
So what's the profound challengethis poses to us?
The author asks pointedly. Will we work hard for something
that can be taken away from us? Will we invest time and energy

(56:37):
even if an outcome is not guaranteed?
If we're driven primarily by ego, the honest answer is often
a resounding no. Why bother if there's no
applause? Right.
But Belisarius, through his unwavering commitment to duty,
accepted this difficult bargain.For him and for us, if we adopt
his mindset, doing the right thing was enough.
The less attached we are to external outcomes, the better

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and more resilient we become. When fulfilling our own internal
standards is what genuinely fills us with pride and self
respect, then the effort, not the results, good or bad, is
enough. Detached from the outcome.
Think of the legendary story of Alexander the Great asking the
philosopher Diogenes what he could do for him, and Diogenes,
the ultimate minimalist. Just replying.

(57:19):
Stop blocking my son. Classic.
Or consider the tragic story of John Kennedy Toole, whose
Pulitzer winning novel A Confederacy of Dunces was
rejected so many times that it contributed to his suicide.
Oh, that's heartbreaking. It is.
The book was equally great, equally brilliant, before it was
published and rewarded. His story highlights just how

(57:39):
arbitrary so many of life's breaks truly are.
We simply cannot allow external validation to determine whether
our work or our lives were worthwhile.
The effort has to be enough. Next, draw the line.
When faced with failure, ego andit's desperate attempt to save
face often compels us to dig a deeper hole rather than accept
responsibility, learn and pivot.Doubling down on stupid.

(58:02):
Pretty much it's that desperate,self-destructive impulse to
reclaim perceived glory, even when it's clearly gone.
We circle back to John DeLorean here, a cautionary tale that
truly reinforces the previous lessons after essentially
running his revolutionary car company into the ground due to
his profound mismanagement and chaotic leadership.
Right, the balloons and lack of order.

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How did he respond to this catastrophic failure?
Not with acceptance or quiet reflection, Oh no.
What did he do? Instead, in a truly bizarre and
desperate act, he orchestrated ajaw-dropping $60 million, a
cocaine deal to try and save hiscrumbling enterprise.
Wait, what? A cocaine deal.
This is where his story takes a truly wild turn.

(58:44):
Delorean's car company was in freefall, collapsing under the
weight of his own hubris and mismanagement, and his audacious
solution was a massive drug deal.
What on earth was he thinking? He was famously caught on video
handling tricks of cocaine, saying with chilling certainty
this stuff is as good as gold. He was in a hole and
increasingly deep one, and he just kept digging.
Wow. Unbelievable desperation.

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This is the classic sunk cost fallacy at play, amplified by a
runaway ego. When our identity becomes
inextricably tied up in our work, our fear of failure is
amplified. We worry that any kind of set
back will say something bad about us as a person.
It feels personal. Exactly.
Ego in that moment of crisis screams why is this happening to

(59:27):
me? How do I save this and prove to
everyone I'm as great as they think I am?
It's a primal, almost animalistic fear of appearing
weak, which often leads us to fight desperately, making things
infinitely worse. What's truly fascinating here is
the stark contrast. De Lorean frantically dug
himself deeper, spiraling into criminality.
But Steve Jobs? Ah.

(59:48):
Of a comeback kid. When faced with an even more
public and humiliating failure, being fired from the very
company he founded, Apple responded by rebuilding his ego
the book admits had made him unmanageable, leading to his
ouster. He wasn't blameless.
Not at all. He cried, he fought, he sold all
his stock and vowed never to think of Apple again.
But then he channeled that energy differently.

(01:00:09):
He went on to start Next Tee andPixar and, crucially, learned
from his management mistakes, actively resolving the flaws
that had contributed to his downfall.
He actually grew from it. He worked relentlessly until he
had not only proven himself again, but had fundamentally
evolved as a leader. That's the critical difference.
Compare jobs to Dov Charney, American Apparel's founder.

(01:00:32):
After his company suffered huge losses and he was fired by his
board, Charney rejected steppingaside.
Instead, he recklessly gambled his entire remaining ownership
in a hostile takeover bid, resulting in more scandals, more
lawsuits, and ultimately bankrupting the very company he
claimed to be fighting for, leaving his own factory workers
jobless. He, like the ancient Greek

(01:00:53):
General Alcibiades, chose to escalate his failures by
defecting between enemies ratherthan ever accepting them.
Just kept making it worse. True recovery, the book reminds
us, is about one step in front of the other.
It's about pausing, drawing thatline and honestly asking
yourself, Is this truly the person I want to be?
Our 4th powerful principle in the face of failure is to

(01:01:14):
maintain your own scorecard. The Inner Game.
This means judging yourself primarily by your own internal
standards and your absolute potential, rather than by
external validation, fleeting temporary wins, or what others
think. It's how you ensure continuous
improvement, even when the worldmight be congratulating you.
The New England Patriots, and specifically the drafting of Tom

(01:01:36):
Brady, provide a fascinating example.
Oh yeah, How so? In the 2000 NFL Drafts, they
picked Brady in the sixth round,a seemingly insignificant 100
and 99th overall pick. It turned out to be arguably the
single greatest draft pick in football history, leading to an
unprecedented dynasty. Absolutely legendary pick.
Yet after all of Brady's Super Bowl wins and accolades, the

(01:01:57):
Patriots front office was astonishingly disappointed in
themselves for the pick. Disappointed.
How could they be disappointed? Let's consider that for a
moment. They won spectacularly big,
achieved what most franchises only dream of, but their honest
internal reaction was self critique.
What does that level of self scrutiny tell you about their

(01:02:17):
mindset? They saw the pick as more lucky
than smart, openly admitting they'd missed or miscalculated
all of his intangible attributes.
Scott Peoli, a director in the organization, even kept a photo
of a failed draft pick on his desk as a constant humbling
reminder. A reminder of failure.
Yeah, you're not as good as you think.
You don't have it all figured out.

(01:02:38):
Stay focused. Do better.
Wow, that's intense self-awareness.
This might sound like a form of self-inflicted torture, but it's
precisely what fuels continuous improvement.
Ego tragically can't see both sides of the coin.
It only focuses on the validation on what's going well
on the scoreboard. But for the Patriots, the
visible scoreboard wasn't their only, or even primary metric.

(01:02:59):
They had an inner scorecard. Exactly.
Warren Buffett makes this brilliant distinction between
the inner scorecard and the external 1.
He says your potential, the absolute best you're capable of.
That's the metric to measure yourself against.
Winning isn't enough. People can get lucky, or frankly
be quite difficult individuals and still win.

(01:03:19):
But not everyone strives to be the best possible version of
themselves. And that's a harsh truth, but it
also offers immense liberation, doesn't it?
It means you can hold your head high, genuinely proud, even in
defeat, if you know in your heart that you gave your
absolute best and adhere to yourown highest standards.
Absolutely. Adam Smith's concept of the

(01:03:39):
indifferent spectator, an objective, impartial judge
within ourselves, provides a fantastic guide for self
judgement, preventing ego from exploiting moral Gray areas or
justifying shortcuts. It's not about what you can get
away with. Exactly.
It's about what you should or shouldn't do.
It's undoubtedly a harder path, initially requiring rigorous
self honesty, but it ultimately makes us less selfish and far

(01:04:03):
less self absorbed. Someone who judges themselves by
these deep internal standards doesn't crave the fleeting
spotlight or wallow and self pity during setbacks.
They can generously share creditand willingly subsume their own
interests for a greater goal because their focus is always on
genuine improvement and impact, not on external applause.
Our final and arguably most challenging lesson when facing

(01:04:25):
failure is to always love. Love your enemies, that's a
tough one. It is the book makes a
compelling case that hate and bitterness are ultimately
self-destructive. Love, or at the very least the
conscious act of letting go, is profoundly empowering and
productive. Consider the infamous feud
between William Randolph Hearst and Orson Welles over Welles
film Citizen Kane. The movie Mobile versus the Boy

(01:04:48):
Wonder. Right.
Hearst, convinced it was an offensive portrayal of him,
launched this all consuming campaign to destroy it.
He leveraged his vast media empire to block screenings,
threaten the studio, spread vicious negative stories about
Welles. Let's really dig into the
absurdity of this Hurst, one of the wealthiest and most powerful
men in America at 78 years old, poured incredible resources into

(01:05:12):
trying to obliterate a movie he probably hadn't even seen.
What a colossal self defeating waste of energy he.
Even offered $800,000 for the rights to the film just so he
could burn every single copy. Burn the negatives.
Wow. The irony, of course, is that
his desperate attempts backfiredspectacularly, inadvertently
cementing the movie's legendary status, what we now call the

(01:05:34):
Streisand Effect. Trying to press it made it
famous. It's almost a cosmic joke.
Attempting to destroy something out of hate or ego often ensures
that it will be preserved and disseminated forever.
That's the painful paradox of hate and bitterness, isn't it?
It achieves the exact opposite of what the ego hopes for.
Exactly. The author poses A challenging
question that cuts right to the bone.

(01:05:55):
What do you dislike? Whose name fills you with
revulsion and rage? Now ask, have these strong
feelings really helped you accomplish anything?
That's a tough mirror to look into.
It is hate, he argues, defers blame.
It's a debilitating distraction,and it is a cancer that gnaws
away at the very vital center ofyour life.

(01:06:16):
It's like carrying this heavy, poisonous backpack every single
day. So what's the profound
implication for our own lives? The author says this obsessive
focus on the past, on how thingsshould have been, is ego
embodied. While everyone else moves on,
learns and builds, you remain trapped.
Frederick Douglass, when faced with profound degradation,
famously declared they cannot degrade.

(01:06:36):
Frederick Douglass, the soul that is within me, no man can
degrade. Powerful self possession.
Martin Luther King Junior taughtthat hate is a burden and that
love was freedom. He consistently urged his
followers and us to look inward,to strip away the ego that both
protects and suffocates us, the very traits that infuriate us
and others, dishonesty, selfishness, pettiness often

(01:06:59):
contain their own inherent punishment.
We don't need to add our misery to theirs.
Right. We don't need to be miserable
simply because others choose to be.
Orson Welles, in beautiful contrast to Hurst, lived a rich,
fulfilling life and remained utterly unbothered by the
campaign against Citizen Kane, proving that you don't have to
descend to the level of those who hate you.

(01:07:20):
But sadly, not everyone is capable of that, are they?
No, the book recounts the painful story of Dave Mustaine,
the guitarist who was famously kicked out of Metallica and went
on to form the incredibly successful band Megadeth.
Right, huge ban. Yet for 18 years, even with his
own massive success and millionsof albums sold, he clung
fiercely to his rage and resentment against Metallica.

(01:07:41):
He admitted that despite his accomplishments, he felt like he
was living under a bridge, consumed by bitterness.
Wow, even with all that success.It's a stark reminder of how ego
can make even a rock star feel like a perpetual failure locked
in a self-inflicted prison of the past.
That obsession with how things should have been is indeed ego
embodied. As we bring this deep dive to a

(01:08:03):
close, the book leaves us with apotent, enduring truth.
The fight against ego isn't a battle you win once and for all.
It's a continuous daily sweepingof the floor.
What images does that evoke for you?
It evokes maintenance, constant vigilance.
Danielle Bolelli, A philosopher and martial artist, uses that
very analogy. Just because you've swept the

(01:08:25):
floor once, it doesn't mean it stays clean forever.
Every single day, dust accumulates.
And every single day you must sweep again.
And that makes us ask a criticalquestion.
What happens if you choose not to sweep?
The tragic example of Dolph Charney, the founder of American
Apparel, serves as a stark, chilling warning.
We saw his earlier failure. What happened next?
After he was finally fired by his board following massive

(01:08:47):
losses, Holiday recalls Charney calling him at 3:00 AM, utterly
convinced he was blameless, justrailing against everyone else.
Yeah. When Holiday cautiously asked if
he would pull a Steve Jobs and maybe start a new company, Yeah.
What do you say? Charney's hollow reply was Ryan.
Steve Jobs died. Whoa, dark.

(01:09:07):
To him, in that addled ego driven state, his failure was
somehow the same as death. For months holiday Watch and
horror is trying to wreak havoc on the company he put everything
into building. It's a sobering thought that but
for the grace of God, that levelof self-destructive ego could be
any of us. It truly is a powerful and
humbling thought, Ryan Holiday wrote.

(01:09:27):
Ego is the enemy, not just as like an academic exercise, but
to share lessons he often learned painfully himself.
He openly admits that as a 19 year old he read Bud Schulberg's
novel What Makes Sammy Run? A classic cautionary tale about
ambition. Right, he understood it
intellectually, yet still managed to make the wrong
choices anyway, working himself into a similar dangerous
situation of ego driven ambitionlater on.

(01:09:51):
There's a powerful quote often attributed to Bismarck that
essentially says any fool can learn from experience.
The trick is to learn from otherpeople's experience.
And this book, this deep dive, offers us precisely that
opportunity, doesn't it? It asks us to look beyond the
surface of ambition and considerwhat it truly means to be a
successful person. Not just successful in terms of

(01:10:12):
external achievements, but in terms of internal character.
Holiday concludes with this powerful, almost provocative
idea. It's certainly admirable to want
to be better businessmen, more skilled athletes, or greater
conquerors, to do truly great things in the world.
We understand that drive now, sure.
But what about striving just as diligently to be better people,

(01:10:32):
happier people, more balanced individuals, more content,
humble and selfless people? The author suggests that
consistently perfecting the personal sphere of our lives
almost invariably leads to success as a professional, but
rarely does it work the other way around.
That's a profound thought. Perfect.
The person, the professional follows.
This deep dive has laid bare howego subtly undermines our

(01:10:55):
aspirations, distorts our perception of success, and
tragically, exacerbates our failures.
It's an ongoing civil war withinus, as Martin Luther King Junior
so eloquently put it. A battle we must wage daily,
consciously. So as you move forward in your
own unique journey, no matter which of these three phases you
find yourself in, aspiration, success, or even failure, how

(01:11:16):
will you choose to battle the ego?
How will you make your choices going forward?
Will you consciously embrace humility, cultivate
self-awareness, and commit to a lentless, unglamorous effort?
Or will you allow that petulant inner child of ego to Stew your
course? The choice, ultimately, is
yours.