WEBVTT

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Welcome to the Deep Dive. I am genuinely excited

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you're joining us for this one today. Oh, absolutely.

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It's a great one. Yeah. You know, we always try

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to picture you, the listener. You're probably

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a lifelong learner, someone who is insanely curious

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about how things work. Right. Maybe you're prepping

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for a big meeting or just trying to catch up

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on a new field. Exactly. But you also absolutely

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hate feeling overwhelmed by information overload,

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which is why we're here. To cut through the noise.

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Right. And to set the mood for today's deep dive,

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I'm looking at your video feed right now, and

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you've got this amazing backdrop. It looks like

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a cozy, kind of dusty library filled with ancient

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texts and philosophy books. Yeah, I wanted to

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set the scene. We're going a bit historical today.

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I love it. So today's topic is a famous aphorism,

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one you have definitely heard and probably used.

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Perfect is the enemy of good. It's everywhere.

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It really is. We are pulling today's insights

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from a remarkably concise but really dense encyclopedic

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article that traces the entire history of this

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exact phrase. The philosophical antecedents,

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the modern variations, all of it. Right. And

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our mission today is to dissect exactly why the

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insistence on perfection often paralyzes us from

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implementing perfectly good improvements. And

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more importantly, to extract practical, memorable

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insights that you can apply immediately. Because

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we want to save you time and energy? We all know

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that sinking feeling of tweaking a project to

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death. Oh, we've all been there. Okay, let's

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unpack this. The basic definition laid out right

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at the top of our source material is striking

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because it frames perfection not as a goal, but

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as a roadblock. Yeah, a massive roadblock. The

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source suggests that achieving absolute perfection

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is, well, it's likely impossible. Therefore,

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the relentless pursuit of it shouldn't stop you

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from recognizing or completing work that is imperfect

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but still highly valuable. And that distinction,

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you know, the difference between flawless and

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useful is really the crux of the issue here.

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It is. In a world of endless information, we

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often confuse flawless with useful. We see curated

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images of success everywhere. Totally. So we

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set a standard that defies reality. And the result

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of demanding that flawlessness is almost always

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paralysis. Like staring at a blinking cursor

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for an hour. Exactly. A useful solution. even

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if it has a few rough edges, actually moves the

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needle. It solves a problem for you or for someone

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else. But a flawless solution that only exists

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in your head. Or is perpetually stuck in a draft

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folder. Right. Sitting in a draft folder because

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it's never quite ready. That helps absolutely

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no one. Ouch. I feel personally attacked by the

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mention of the draft folder. But it really begs

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the question, why is that our default state?

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Well, tinkering feels like productive work. As

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long as you are endlessly revising. or adjusting

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fonts, or doing just a little more research.

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Oh, but endless research. Right. You are protecting

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yourself from the vulnerability of actually shipping

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a finished product. Perfectionism is often just

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procrastination wearing a really nice suit. Wow.

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That is a harsh but completely necessary reality

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check. So where does this idea actually come

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from? Because Voltaire usually gets all the credit

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for this, right? The French Enlightenment philosopher.

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He does. In the English -speaking world, the

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most famous attribution points to Voltaire in

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1770. Okay, 1770. Yeah, in his work, Questions

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sur l 'Encyclopédie, he quoted an Italian proverb.

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He wrote, Il meglio è l 'inimico del bene. The

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best is the enemy of the good. Right. And he

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clearly found the concept compelling because

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he used it again in his moral poem, La Beghe.

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He wrote about a wise Italian who says that the

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best is the enemy of the good. I have a really

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hard time believing an 18th century philosopher

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was the very first person to realize perfectionism

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is a trap, though. Does this go back further?

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Oh, it absolutely does. While Voltaire popularized

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it, another French philosopher, Montesquieu,

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beat him to the punch by several decades. Oh,

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really? Yeah, around 1726, in his work Pensée,

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Montesquieu wrote something very similar, but

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with a slight, incredibly impactful variation.

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He wrote, Le mieux est le mortel ennemi del bien.

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Translated, that is, the best is the mortal enemy

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of the good. Exactly. The mortal enemy. That

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shifts the tone completely. It changes the entire

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weight of the phrase. By adding the word mortal,

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Moscow is emphasizing that perfection doesn't

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just oppose the good. It literally kills it.

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Yes. The pursuit of the absolute best actively

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destroys the perfectly good reality you could

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have achieved. It's like assassination by overtinkering.

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You aren't just delaying your work, you are murdering

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its potential. What's fascinating here is that

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the roots of this idea stretch back way past

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the French Enlightenment, all the way to the

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ancient world. So your library background is

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really paying off right now. I told you. Specifically...

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We can look at Aristotle and his principle of

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the golden mean. The golden mean, the idea of

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finding the middle path between two extremes.

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Right. And we usually think of the golden mean

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in terms of emotional extremes. Yeah. Like finding

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the balance between recklessness on one end and

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cowardice on the other. Sure. But applying it

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to work ethic is a brilliant paradigm shift.

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The golden mean counsels against all extremism.

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And perfectionism is, by definition, an extreme.

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That makes a lot of sense. It is a fundamental

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refusal to accept the reality of human limits.

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By striving for the absolute extreme of flawlessness,

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you abandon the balanced rational middle ground

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of creating something good and useful. That totally

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reframes how I look at my own to -do list. We

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don't usually label ourselves as extremists when

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we're just trying to get a project exactly right.

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We really don't. But the literature backs this

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up, too. The overarching philosophy shows up

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vividly in English literature. Most notably was

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Shakespeare. Oh, yes. In his tragedy, King Lear,

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which was written around 1606, the Duke of Albany

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gives this warning. He says, striving to better,

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oft we mar what's well. Such a great line. And

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Shakespeare hits on the exact same theme in Sonnet

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103. He writes, Were it not sinful then, striving

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to mend, to mar the subject that before was well.

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Striving to mend, to mar the subject. It is a

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beautiful, poetic... description of self -sabotage

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it really is yeah and to make it feel a bit more

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modern for you listening right now think about

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a time you were working on a presentation oh

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boy you have a perfectly good slide deck the

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information is clear the narrative makes sense

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but you just keep striving to mend it just one

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more tweak right You change the font, you adjust

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the margins by a millimeter, you try a new transition

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effect, and suddenly the formatting for the entire

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deck is completely ruined. You strove to better

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it, and you marred what was well. I can actually

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speak to that from personal experience. You tell.

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I once spent three days reformatting a data report

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to make the charts look aesthetically flawless.

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And in the process of moving everything around,

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I accidentally deleted a crucial column of raw

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data that altered the final conclusion. I had

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to revert to a saved version from three days

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prior. I hit undo on 72 hours of my life. That

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is brutal. That is Shakespeare's warning playing

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out in real time. Well, here's where it gets

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really interesting. Let's transition away from

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your dusty library backdrop for a second. Let's

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imagine we are now sitting in the middle of a

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bustling modern airport terminal. Okay, shifting

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gears. I like it. Because the applications of

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this concept become intensely practical in the

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real world. Before we get to the literal airplanes,

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our source introduces a proverb from an 1893

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dictionary of quotations said to be of Chinese

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provenance that provides a stunning visual. Okay,

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what's the quote? Better a diamond with a flaw

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than a pebble without one. That imagery perfectly

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encapsulates the shift from theory to reality.

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Isn't it? A diamond has immense intrinsic value.

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Even if it has a flaw, a cloudy spot, or a small

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inclusion, it remains a highly valuable gem.

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A pebble, on the other hand, might be perfectly

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smooth, perfectly round, absolutely flawless

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in its execution as a pebble. But at the end

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of the day, its intrinsic value is virtually

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zero. It's still just a rock. Exactly. When you

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apply this to your daily life, a flawed but completed

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project, a product launched, a tough conversation

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had, a decision made that is your diamond. It

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exists in the real world. It has real, tangible

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value. An incomplete, theoretical perfect project

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that you never finish is just a pebble. You might

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have flawless ideas in your head, but without

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the flawed reality of execution, they carry absolutely

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no weight. I see the logic. But let me play devil's

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advocate for just a second. Go for it. I'm looking

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around this metaphorical airport terminal we're

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sitting in. If I'm getting on a plane I really

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want the mechanic who checked the jet engine

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to be a perfectionist. Fair point. I do not want

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a flawed diamond of an airplane engine. Doesn't

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this whole philosophy break down when the stakes

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are literally life and death? That is a completely

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fair pushback, and context is everything here.

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In highly constrained, zero -tolerance environments,

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aviation mechanics, structural engineering, neurosurgery,

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the good is explicitly defined by extreme precision.

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So perfection is the baseline. Or as close to

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it as humanly possible, yes. But the trap is

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that we take the standard required for a jet

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engine and apply it to a weekly newsletter, or

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organizing our garage, or writing a first draft.

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That makes a lot of sense. Most of us are not

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performing open heart surgery at our desks. We

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artificially inflate the stakes of our own work

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to justify our perfectionism. Precisely. And

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what's interesting is that even in life or death

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scenarios, speed sometimes still trumps perfection.

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Really? Yes. The history of the military and

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the tech sector provides a phenomenal example

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of this. Robert Watson Watt, who was heavily

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involved in the development of radar during World

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War II. Huge stakes. Massive stakes. He propounded

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what he called a cult of the imperfect. A cult

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of the imperfect. I love that phrasing. The guiding

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rule of his cult is incredibly pragmatic. He

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stated, give them the third best to go on with.

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The second best comes too late. the best never

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comes. The third best, not even the second best.

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Right. Because in a rapidly evolving high stakes

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environment like military defense, speed and

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implementation are infinitely more critical than

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delayed perfection. That makes total sense. If

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you wait to engineer the absolute best radar

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system, the war might be over before you deploy

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it. If you wait for the second best, you've still

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lost critical time and likely lives. The third

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best is the good improvement that you can implement

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today. The enemy isn't going to pause their advance

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while you tinker with your prototypes. It's the

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ultimate reality check. Perfection is a luxury

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you literally cannot afford when time is of the

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essence. Exactly. Which brings us perfectly back

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to our bustling airport setting and an incredible

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assertion from the economist George Stigler.

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He famously said, if you never miss a plane,

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you're spending too much time at the airport.

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If we connect this to the bigger picture, Stigler

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is offering a master class in opportunity cost.

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Let's break that down for the listener. In economics,

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opportunity cost is the potential benefit you

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lose when you choose one alternative over another.

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In this case, the cost of a flawless travel record

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is the hundreds of hours of your life you lose

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sitting at a departure gate. Okay, unpack that

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a bit more, because missing a plane sounds like

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a massive failure to most people. It does, which

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is exactly why we overcompensate. Think about

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what it takes to never miss a plane over the

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course of your entire life. A lot of waiting.

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A ton of waiting. To guarantee a 100 % success

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rate, to be perfectly prepared for unexpected

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traffic, long security lines, or a delayed shuttle,

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you might arrive at the airport three or four

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hours early every single time you travel. Yeah,

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we all know someone who does that. Over decades,

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that equates to weeks of your life spent sitting

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in an uncomfortable chair waiting to board. Stigler

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is arguing that if you are perfectly prepared

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for every single variable in your life, you are

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wasting a massive amount of your most valuable

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resource, which is... Because occasionally missing

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one plane in a 10 -year span is actually a cheaper

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price to pay than wasting weeks of your life

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sitting in a terminal just to maintain a flawless

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record. Exactly. The pursuit of the flawless

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travel record is a massive misallocation of resources.

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The flaw of missing a flight once a decade is

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the necessary, acceptable byproduct of living

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an optimized, efficient life where you don't

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waste your time. That completely flips the script

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on how we view preparation. The goal isn't to

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avoid failure at all costs. The goal is to price

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the failure correctly. Beautifully said. I think

00:12:38.309 --> 00:12:40.789
a lot of us need to audit our own lives and figure

00:12:40.789 --> 00:12:42.570
out where we are currently sitting at the gate

00:12:42.570 --> 00:12:45.110
for four hours. We absolutely do. We naturally

00:12:45.110 --> 00:12:49.029
fear the acute, highly visible pain of a failure,

00:12:49.190 --> 00:12:52.470
like missing the flight or publishing a typo,

00:12:52.470 --> 00:12:55.610
much more than we notice the chronic, invisible

00:12:55.610 --> 00:12:58.509
drain of the wasted time it took to prevent it.

00:12:58.860 --> 00:13:01.159
And this concept of over -optimization bleeding

00:13:01.159 --> 00:13:04.200
into wasted time is a foundational rule in computer

00:13:04.200 --> 00:13:07.340
science, too. Oh, definitely. Donald Knuth, a

00:13:07.340 --> 00:13:09.740
giant in the field of computer programming, has

00:13:09.740 --> 00:13:16.059
a famous statement. He said, In the programming

00:13:16.059 --> 00:13:18.679
world, premature optimization means that developers

00:13:18.679 --> 00:13:21.559
try and make their code run perfectly fast. or

00:13:21.559 --> 00:13:23.879
use perfectly minimal memory before they even

00:13:23.879 --> 00:13:26.200
know if the basic program actually works to solve

00:13:26.200 --> 00:13:28.179
the problem in hand. So they're fixing problems

00:13:28.179 --> 00:13:31.039
that might not even exist yet. Exactly. Imagine

00:13:31.039 --> 00:13:33.379
spending weeks optimizing a sorting algorithm

00:13:33.379 --> 00:13:35.820
for a database that only has 10 items in it.

00:13:36.120 --> 00:13:38.620
It's a massive waste of time, it makes the code

00:13:38.620 --> 00:13:41.100
overly complex, and it distracts from the actual

00:13:41.100 --> 00:13:42.860
goal, which is building a functional piece of

00:13:42.860 --> 00:13:44.919
software. You're polishing the diamond before

00:13:44.919 --> 00:13:47.919
you even dug it out of the mine. Yes. And while

00:13:47.919 --> 00:13:50.240
Truth was talking about code, this applies to

00:13:50.240 --> 00:13:53.629
everything. Premature optimization is the writer

00:13:53.629 --> 00:13:56.809
who spends three weeks picking the perfect font

00:13:56.809 --> 00:13:59.549
and formatting their title page before they've

00:13:59.549 --> 00:14:02.210
written chapter one. Guilty. It is the person

00:14:02.210 --> 00:14:05.029
who spends five days organizing a flawless digital

00:14:05.029 --> 00:14:08.429
workspace with color -coded tags to manage a

00:14:08.429 --> 00:14:11.090
project they haven't actually started yet. Or

00:14:11.090 --> 00:14:14.269
buying the absolute highest end, perfectly engineered

00:14:14.269 --> 00:14:17.210
running shoes before you've even proven to yourself

00:14:17.210 --> 00:14:19.830
you can jog around the block consistently. The

00:14:19.830 --> 00:14:22.269
optimization becomes a distraction from the execution.

00:14:22.590 --> 00:14:25.549
We use the preparation to avoid doing the actual

00:14:25.549 --> 00:14:28.750
work. And in the business world, this phenomenon

00:14:28.750 --> 00:14:31.470
actually have a name. In marketing and product

00:14:31.470 --> 00:14:34.230
development, there is a recognized concept called

00:14:34.230 --> 00:14:38.090
quality creep, and it is viewed as actively counterproductive

00:14:38.090 --> 00:14:40.690
to success. Quality creep is a very specific,

00:14:40.929 --> 00:14:44.370
very dangerous trap. It happens when a team keeps

00:14:44.370 --> 00:14:47.299
adding features. or endlessly polishing a marketing

00:14:47.299 --> 00:14:50.120
campaign well beyond what the consumer actually

00:14:50.120 --> 00:14:52.159
needs or cares about. So you're just sinking

00:14:52.159 --> 00:14:54.600
money and labor into it. Right. You are sinking

00:14:54.600 --> 00:14:58.000
hours into pushing a product from 95 % good to

00:14:58.000 --> 00:15:01.720
99 % good. But the reality of the market is that

00:15:01.720 --> 00:15:04.220
the customer was already entirely satisfied and

00:15:04.220 --> 00:15:08.559
ready to buy at 90%. Wow. That extra 9 % of quality

00:15:08.559 --> 00:15:11.659
you chased is counterproductive because the return

00:15:11.659 --> 00:15:14.039
on investment for that effort is effectively

00:15:14.039 --> 00:15:18.049
zero. You've marred what was well by trying to

00:15:18.049 --> 00:15:20.769
mend it for no practical reason. So what does

00:15:20.769 --> 00:15:22.990
this all mean? We have covered a massive amount

00:15:22.990 --> 00:15:25.149
of ground today. We really have. And the through

00:15:25.149 --> 00:15:27.850
line connecting all of these distinct ideas is

00:15:27.850 --> 00:15:31.429
incredibly clear across centuries, from the ancient

00:15:31.429 --> 00:15:33.909
wisdom of Aristotle counseling against extremes

00:15:33.909 --> 00:15:36.950
to Shakespeare warning us about marring what

00:15:36.950 --> 00:15:39.429
is well. Right up to modern economists, military

00:15:39.429 --> 00:15:42.460
strategists, and computer programmers. The consensus

00:15:42.460 --> 00:15:45.820
is undeniable. Flawlessness is a trap. Good enough

00:15:45.820 --> 00:15:48.320
isn't a compromise, and it isn't a failure. It

00:15:48.320 --> 00:15:50.960
is very often the smartest, most strategic goal

00:15:50.960 --> 00:15:53.879
you can aim for. It is the optimal strategy for

00:15:53.879 --> 00:15:56.320
navigating a reality where you have finite time

00:15:56.320 --> 00:15:59.000
and finite resources. You simply cannot afford

00:15:59.000 --> 00:16:02.019
to be perfect. So, to you listening right now.

00:16:02.519 --> 00:16:04.860
When you are absorbing new information, when

00:16:04.860 --> 00:16:06.840
you are doing research for that big presentation,

00:16:07.220 --> 00:16:09.740
or when you are just trying to finally finish

00:16:09.740 --> 00:16:11.919
a task that has been lingering on your desk for

00:16:11.919 --> 00:16:15.759
weeks, I want you to actively embrace the flawed

00:16:15.759 --> 00:16:18.320
diamond. Stop trying to smooth it into a useless

00:16:18.320 --> 00:16:20.860
pebble. Give them the third best to go on with.

00:16:21.370 --> 00:16:23.750
Respect your own time enough to risk occasionally

00:16:23.750 --> 00:16:26.610
missing a metaphorical plane. Your energy is

00:16:26.610 --> 00:16:29.149
entirely too precious to spend sitting at the

00:16:29.149 --> 00:16:31.669
departure gate of perfection. This raises an

00:16:31.669 --> 00:16:33.590
important question, though, and it's something

00:16:33.590 --> 00:16:35.690
I want to leave you to ponder as you step back

00:16:35.690 --> 00:16:37.669
into your day. Okay, let's hear it. We've established

00:16:37.669 --> 00:16:40.529
that perfection kills the good, and that striving

00:16:40.529 --> 00:16:44.470
to mend often mars what is well. But if the pursuit

00:16:44.470 --> 00:16:47.549
of perfection actively destroys the good, How

00:16:47.549 --> 00:16:50.289
do we identify that exact invisible tipping point?

00:16:50.409 --> 00:16:52.570
That is the big question. Is there a measurable

00:16:52.570 --> 00:16:55.610
moment in our work, a specific minute of editing

00:16:55.610 --> 00:16:58.149
or tweaking a design? We're researching one more

00:16:58.149 --> 00:17:01.250
article where our genuine desire to improve secretly

00:17:01.250 --> 00:17:03.929
transforms into the destruction of our own progress.

00:17:04.509 --> 00:17:06.789
Finding that invisible line where the return

00:17:06.789 --> 00:17:10.170
on investment drops to zero. Exactly. Next time

00:17:10.170 --> 00:17:12.410
you find yourself endlessly revising a project,

00:17:12.609 --> 00:17:15.109
stop and ask yourself, have I already crossed

00:17:15.109 --> 00:17:17.829
the line from polishing the diamond to crushing

00:17:17.829 --> 00:17:20.829
it into a pebble? That is such a brilliant, challenging

00:17:20.829 --> 00:17:23.250
thought to leave off on. Are you polishing the

00:17:23.250 --> 00:17:25.910
diamond or are you crushing it? Thank you so

00:17:25.910 --> 00:17:27.670
much for joining us on this deep dive. It's been

00:17:27.670 --> 00:17:30.190
a pleasure. We love unpacking these concepts

00:17:30.190 --> 00:17:32.069
and figuring out how to apply them alongside

00:17:32.069 --> 00:17:34.950
you. Now get out there, stop over -optimizing,

00:17:34.970 --> 00:17:37.950
and boldly make some perfectly good, gloriously

00:17:37.950 --> 00:17:40.230
imperfect things. We will catch you next time.
