To Be or Not To Be a Mastermind | #4

Summary

Decoding Taylor Swift: A Storytelling Revolution — Episode 4

To Be or Not To Be a Mastermind | July 22, 2025

Hosts: Joe Romm & Toni Romm
Theme: Dissecting Taylor Swift’s “Mastermind” as a masterclass in intentional storytelling and strategic communication, drawing parallels to Shakespeare and providing universal lessons on how to become a better communicator, creator, and leader.

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Overview of the Episode

In this rich and witty discussion, Joe and Toni Romm decode Taylor Swift’s song “Mastermind” to reveal its storytelling brilliance and the powerful lesson at its core: the necessity of intention and design in every word you use—whether in songs, speeches, or life. With references ranging from Shakespeare’s Hamlet to the craft of pop songwriting and feminist agency, this episode dives deep into how “Mastermind” exemplifies narrative strategy, ironies, and multi-layered meaning. The Romms also draw actionable lessons for listeners, ensuring this episode not only transforms how you hear Swift but how you communicate and influence.

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Key Discussion Points & Insights

The Power of Storytelling by Design

• Intentionality in Communication

  • “As Taylor says in her song, she does everything by design. When you write, you need to do everything by design. You need to make every word count…” (Joe, 00:47)
  • Great writers and storytellers—like Swift and Shakespeare—choose every word for a purpose. If a word’s purpose isn't clear, cut it.
  • This is the single most crucial secret for writing, storytelling, and even success in life.

• Machiavellian Strategy

  • Swift identifies herself as “cryptic and Machiavellian” because she cares, referencing the calculating methods described by Machiavelli: “She is taking explicit care to write her lyrics…with one specific end goal in mind.” (Toni, 02:37)
  • Stephen Covey’s advice, “Start with the end in mind,” is invoked to reinforce narrative design (Joe, 03:47).

Shakespearean Parallels: “To Be or Not To Be” (04:59–14:44)

• Strategic Word Choice & Foreshadowing
  • Swift’s lyric philosophy is rooted in Shakespearean practices, such as using foreshadowing and karma: “The foreshadow is what goes around and the irony is what comes around.” (Joe, 04:47)
• Deep Dive into Hamlet's Soliloquy
  • The famous “to be or not to be” speech is analyzed to demonstrate how even surface-level ambiguities hold immense meaning, with every word chosen for narrative impact (Joe & Toni, 05:21–13:14).
• Application to Mastermind
  • Both Shakespeare and Swift “cram a lot of meaning into those few lines.” (Joe, 10:05)
  • By dissecting Hamlet, the Romms teach listeners how to achieve depth and coherence in their own communication.

Decoding “Mastermind” — Text, Structure & Irony (15:21–37:00)

• Opening Irony & Narrative Reversal

  • “Once upon a time…” — Swift begins with classic fairy tale language, but always with heavy irony: “Whenever she uses Once Upon a Time, it’s always steeped in irony. It’s always very sarcastic.” (Toni, 16:38)
  • The episode draws a link to Swift’s other songs (“I Knew You Were Trouble”) to show her habit of reversing tropes and layering irony (Joe & Toni, 20:33–21:28).

• Confession and Villainy

  • Behind the fairy tale facade is confession and agency: “She wanted the chorus to sound like a villain had just entered the room.” (Joe, 18:27)
  • “What if I told you none of it was accidental…What if I told you I’m a mastermind and now you’re mine?” (Taylor Swift lyric, quoted at 17:47)

• Feminism and Reclaiming Power

  • “All the wisest women had to do it this way. Because we were born to be the pawn in every lover’s game. If you fail to plan, you plan to fail…” (Taylor Swift lyric, read by Toni, 22:32)
  • Toni gives a candid perspective on how women have historically had to work “behind the scenes by pulling the strings,” with a nuanced take on power and privilege (23:08–23:58).
  • Joe adds: “You cannot be a pop songwriter if you’re not calculating. Pop songs are the most calculated thing there is.” (28:15)

• Addressing Criticism and Gendered Labels

  • The label “calculating” is gendered: “They don’t use those words about any man. I don’t know that I’ve ever heard a man accused of being calculating.” (Joe, 27:44)
  • Swift’s embrace of the accusation is a form of empowerment and narrative subversion.

• The Bridge: Hyperbole and Origin Story

  • Lyric: “No one wanted to play with me as a little kid, so I’ve been scheming like a criminal ever since to make them love me and make it seem effortless…” (read at 29:19)
  • The hosts discuss the (slightly exaggerated) origin story, tying it back to the hero’s journey and the way personal pain can fuel narrative agency.

• Layers of Irony and the Song’s Ending

  • The “twist” ending—“you knew the entire time”—sparks debate:
    • Toni’s critique: “I don’t love that she’s kind of undermining her entire cold and calculating nature by saying that he knew the entire time…” (Toni, 33:36)
    • Joe’s theory: “If I’m so calculating, how do you know that I’m calculating?...Apparently, I’m not so calculating that I’ve been able to fool you.” (34:17)
  • The ambiguity allows for multiple readings—addressing both fans and critics, offering both specificity and universality.

Lessons for Communicators and Creators (35:04–41:24)

• Multiple Meanings & Audience Engagement

  • Great storytelling delivers “multiple meanings…to affect different people differently,” enabling both broad and specific appeal (Joe, 36:20).
  • Swift and Shakespeare both succeeded in addressing audiences at many levels—fans, critics, and the general public—without sacrificing artistry.

• Practical Homework & Life Applications

  • Advice: Outline the effects you want before creating—“Make sure that every single word…goes to that effect.” (Toni, 39:06)
  • “Clarity of purpose” and developing a “voice with internal consistency” are critical (Joe, 40:03–40:11).
  • The journey from outsider to “mastermind” is a classic hero’s arc, applicable to anyone seeking to lead, connect, or change the world.

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Memorable Quotes & Moments

• On Ruthless Editing:

  • “If you have an effect in mind and your words aren’t being used to achieve it, cut them the hell out.”
    —Toni, 01:43

• The Shakespeare Parallel:

  • “You have the foreshadow is what goes around and you have the irony is what comes around.”
    —Joe, 04:47

• Feminist Insight:

  • “Behind every great man, there’s a woman. And that’s because the only way that women in the past have been able to exert power and decision making is from behind the scenes by pulling the strings.”
    —Toni, 23:58

• On Calculated Artistry:

  • "You cannot be a pop songwriter if you’re not calculating. Pop songs are the most calculated thing that there is. There’s a formula..."
    —Joe, 28:15

• Irony of the Mastermind Label:

  • “If I’m so calculating, how do you know that I’m calculating? Apparently, I’m not so calculating that I’ve been able to fool you.”
    —Joe, 34:17

• Empowering Lesson:

  • “This is the secret to writing by design. And also coherently. You have to know the ending that you’re going for from the very first word.”
    —Joe, 38:28

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Important Timestamps

• 00:43–02:37: The premise of intentional design and Machiavellian creation in Swift’s and all storytelling.
• 04:59–14:44: Deep dive into Hamlet’s soliloquy, word-by-word analysis, and relevance to Swift.
• 16:10–21:28: Dissecting “Mastermind” opening lines, Once Upon a Time motif, and strategic irony.
• 22:32–27:58: Discussion on feminist strategy, societal expectations, and power through planning.
• 29:19–34:17: The bridge, hyperbolic autobiographical elements, and narrative subversion.
• 36:20–38:28: Crafting stories with multiple layers of meaning; the ultimate writing advice.
• 39:06–41:24: Life lessons, actionable writing strategies, and closing motivational guidance.

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Final Takeaways

• Every word counts: Excellence in storytelling (and viral communication) comes from intentional, strategic word choice.
• Embrace agency: Whether called “calculating” or “Machiavellian,” using design to shape your life and your art is a strength—not a flaw.
• Multiple meanings = virality: The greatest works, from Shakespeare to Swift, are those that can be universal and specific, timeless and personal—a masterclass in connection.
• Be your own mastermind: Plan with purpose, write by design, and turn critique into empowerment.

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Transcript

[A]

Hi, I'm Joe Rome and I'm his daughter, Toni.

[B]

Welcome to Decoding Taylor Swift, where you'll learn the storytelling tools Swift uses that make her a modern day Shakespeare, but.

[A]

Can make you a better communicator so you can drive your mission and build your tribe.

[B]

Rolling Stone magazine put both me and Swift on its list of 100 people changing America. So I know that the most successful social change makers are the best storytellers.

[A]

This podcast will transform how you think about Swift's songs and give you the life changing tools to lead, connect and change the world.

[B]

Hello.

[A]

Howdy.

[B]

Welcome to episode four where we're going to talk about Taylor Swift's mastermind. And you're going to learn maybe the most important secret in writing and perhaps even for success in life. Certainly, certainly in storytelling, certainly in storytelling and even in the larger world. But the main point here is, as Taylor says in her song, she does everything by design. When you write, you need to do everything by design. You need to make every word count, have a reason for putting everything in. Every word that you put in a story, you need to have a reason for it. And if you don't know the reason, you should take it out. Because the great storytellers, they are careful about every word they choose.

[A]

Yes. This is about one of the most, one of the most important lessons that any writer that you can learn. If you want to be a successful storyteller, you have to be very, very.

[B]

Strategic.

[A]

Yeah, you have to be very strategic. You, you have to be very intentional with the words that you use. But if you have an effect in mind and your words aren't being used to achieve it, cut them the hell out.

[B]

A key point that we will, we will come to, which is the more meaning that you want to cram into your story, your speech, or you're giving a euro.

[A]

Even if you're talking to somebody that you're trying to impress. I mean, like, this is the single most important thing you can do, is plan out your thoughts.

[B]

And as we will see, that's what she does in Mastermind. And in fact, she says in her song, besides the fact that she says everything that she does is by design. She says I'm only cryptic and Machiavellian because I care. So she is, she cares, she cares. Sometimes she seems cryptic, as we have seen and as we'll see. But it's all to a purpose, right?

[A]

And we can dive into what it means to be Machiavellian specifically, because obviously Machiavelli, famous 15th and 16th century writer, who was famous for probably his most famous work, El Principe, which means the prince in Italian, if you guys didn't know, sorry, I'm Italian. So I just kind of had to say that. But he was famous for writing probably what most philosophical scholars, somebody who's into philosophy, consider to be one of the first works of modern philosophy. Because it's especially political philosophy. Political philosophy because it started to put the practical effects of an action on the same level as kind of the theory or the ideal effects that kind of had been. Had been, you know, oh my God, words aren't coming to my brain. That had been pioneered, that's the word, by Plato, Aristotle and the ancient Greek philosophers. But so when Taylor says she's being Machiavellian, it means that she is taking explicit care to write her lyrics. But you know, she has to have one specific end goal in mind.

[B]

As Covey said in the 7 Habits of Highly Effective People, start with the end in mind. Know how this is going to end before you start, because everything is going to drive forward towards that. And this gets back to the point we made in the very first. First episode.

[A]

Yes, it did.

[B]

Which was about foreshadow. From the very first word. You have to anticipate the ending.

[A]

Yes.

[B]

And you're going for coherence. One of the points that we've been making here is that Taylor Swift is a modern day Shakespeare.

[A]

Yes.

[B]

And I wanted to illustrate that Shakespeare himself followed this very principle, that this.

[A]

Maxim, one could say maxim.

[B]

And it's been a basic tenant of how you write poetry, how you write great literature, that you choose every word carefully, that you use foreshadow. And the foreshadow. We talked about karma. What goes around comes around. You have the foreshadow is what goes around and you have the irony is what comes around.

[A]

Right. And that's the karma.

[B]

And like I said, when you master this holistic approach or mastermind this holistic approach.

[A]

Right.

[B]

Then this is the ultimate goal in not going to say that you could be Shakespeare or Taylor. It's about you being the best possible writer that you can be. That's what we're after here, how you can be the best possible writer. So let's talk a little bit about one of the most famous speeches in all literature.

[A]

Yeah, sure.

[B]

The to be or not to be speech.

[A]

It is true. Well, technically it's a soliloquy.

[B]

It is a soliloquy and it's one of the most quoted opening line, one of the most quoted lines in all of Literature. To be or not to be, that is the question. But let's try to dig into these lines which aren't so well understood, but there's a very interesting backstory here.

[A]

I guess there is. Backstory alert. He's gonna start talking about this, so I'm just gonna cover my ears.

[B]

You can't cover your ears. You memorized the to be or not to be speech when you were, I don't know, two or three.

[A]

Nerd alert.

[B]

Don't remember I taught you the entire to be or not to be speech.

[A]

Yeah, double nerd alert.

[B]

And you were very good at it.

[A]

Aw, thanks.

[B]

And I was actually telling, literally I was telling someone this when I was recently on travel first for some speaking engagements and someone and I said, I taught my like 3 year old daughter how to do the to be or not to be speech. And she said, well, how did you do that? But of course that meant I had to sing.

[A]

I don't think it did. Just like I don't think it did. But I'm, you know, I'm glad that you're embracing that part of yourself and I love you.

[B]

This is the only time I will sing on this show.

[A]

Oh, you're gonna do it now?

[B]

I will just. Well, how do you, how do you teach a three year old the to be or not to be speech?

[A]

You say it at them until like they get sick. Or you can Pavlovs dog them and you can, you can kind of reverse do that. You, like, give them a treat whenever they, like, hear it. And so whenever they hear it, they get happy because there's going to be a treat.

[B]

These are all possibilities.

[A]

Yeah.

[B]

Or you might say, why don't I use the great trick from the ancient bards? I'm going to put it to music that they know because that's one of the things that they learned in the ancient tribes was that when you set things to music, it was easier to remember. So this is all about, right, being memorable. We talked about the whole point of when you write something, you're trying to be memorable. So that's what singing is for. So what I realized is, well, why don't I teach you the song to be or not to be, and let's just put it to the tune that you already know. And so it went something like this. Sorry, apologies. To be or not to be. That is a question. Whether tis nobler in the mind to suffer the slings and arrows of outrageous fortune.

[A]

Yeah, clearly the syllables were a little bit, a little bit scrunched or to.

[B]

Take arms against a sea of troubles and by opposing end them. So that's how I did it. That's how I did it. And you did it. You did it. You learned it.

[A]

Yeah. I'm sad I forgot it because that would have been a really cool party trick. Like, I know mom used to, like, haul me around to, like, parties and be like. And like, bring, like, one of the picture books that I memorized. Because when I was three, I like. Or two and three, I, like, memorized books that she read at me. And then she would go around and apparently pretend like I could read at 2. I couldn't. I just memorized the books.

[B]

I just want you to know that it never occurred to me like a.

[A]

Baby sack and made me sing it for people.

[B]

Well, let's dive in. Let's dive in to what those words mean, because they have confused a lot of people.

[A]

They have.

[B]

On the surface, they actually.

[A]

They have. Yeah, they have. Many in English class, many of my English class and AP lit this year. Not me, though, can never be confused.

[B]

And as I've said before, kind of got obsessed about Shakespeare over the years, just a tad. So as with before Taylor's cryptic words, before hers bothered me and I had to obsess about them, and before you.

[A]

Understand Taylor, you really do have to understand Shakespeare. Before you understand, you know, any. Any great communication, you have to understand Shakespeare because he did form the basis for a lot of it. Whether you like him or not, whether you think he needs to be, you know, taught as much as he is in schools, he is one of the greatest writers of all time.

[B]

Well, look, I personally agree, if you want to master communications and storytelling, you should study Shakespeare. But part of the reason doing this podcast is because I realized, well, not everybody feels that Shakespeare is so accessible.

[A]

I agree. Right. I mean, like, the language is quite hard to parse. That's what makes it so difficult to teach in a lot of schools. I think a lot of the arguments is that, is that it is really inaccessible. And so, you know, we're going to try to give you a little sneak peek. Well, let's make it accessible.

[B]

Let me. Let me show that what appears to be a little opaque on the surface is Shakespeare cramming in a lot of meaning into those few lines.

[A]

Yeah. And after you. And after you hear the to be or not to be and the really, like, deep shreds of meaning that are conveyed really in each word, like, you will understand and you will be able to learn how to convey the same meaning in your writing.

[B]

Yeah. And ultimately, that's why we have chosen to use Taylor lyrics as the syllabus, because they're much more accessible. But remember, Taylor herself said she loves Shakespeare, and she quotes him again and again, including Hamlet. So it's clear she read Shakespeare to become a better writer. And we can, too.

[A]

Yeah. All right.

[B]

So anyway, so the lines say, you know, to be. So it says, to be or not to be. That is the question whether tis noble in the mind to. Whether tis nobler in the mind to suffer the fortune.

[A]

Suffer the slings and arrows of outrageous fortune.

[B]

So that's what to be is. To be is to suffer the slings and arrows of outrageous fortune.

[A]

Sure. In other words, you know, live. Go through your life.

[B]

Right.

[A]

Feel the things that you feel.

[B]

And look, Hamlet. You'd feel as besieged as Hamlet, Right. If your father died, your mother married your uncle, and your father's ghost showed up and said, you, uncle killed him and you must get revenge.

[A]

And you were 19 when this happened. That's a lot like, I'm 18, and I think that I would, like, genuinely have a psychological break if that happened to me.

[B]

It's a lot to take for a college kid.

[A]

Definitely would be. And it'd be weird if mom married Danny.

[B]

But what's odd about that parallel structure here is that that means that not to be is the same as ending your troubles by taking up arms against them.

[A]

Right. Which is kind of, on the surface, odd.

[B]

Odd, because isn't ending your troubles the obvious choice?

[A]

Right. Wouldn't you want to end your troubles?

[B]

Right.

[A]

And taking up arms against a sea is also not something that people tend to do.

[B]

That's called a mixed metaphor.

[A]

Right.

[B]

And indeed, if you. Shakespeare has often been criticized for using.

[A]

A mixed metaphor, as has Taylor.

[B]

As has Taylor. You can't take arms against the sea. Right. That would be completely futile. Right. A weapon against the ocean. Right. That would be kind of pointless. But the point is, is it likely that Shakespeare made such a simple mistake?

[A]

Right.

[B]

The answer, of course, is no.

[A]

Silly.

[B]

Once you realize that every word is chosen for a reason, then you can put the equation together. He's saying that taking up arms for revenge. That by taking up arms for revenge, Hamlet is ending his troubles and himself.

[A]

Right.

[B]

And we know that's what he means, since it foreshadows the actual ending where Hamlet does take up arms.

[A]

Spoiler alert.

[B]

He does kill his troubles, but at the same time that they kill him in his duel with Laertes.

[A]

Yeah, just a big spoiler alert.

[B]

Sorry about that.

[A]

I mean, because like, if you're listening to this and you haven't taken AP lit and they haven't made you read like Hamlet, it's going to be a real shock when he dies.

[B]

Yeah. Particularly this whole. You missed the title tragedy of Hamlet.

[A]

But don't worry, not everyone in the little circle of his gaggle dies. And I'm going to leave it at that because I don't want to spoil. So you now have you still something to read for if your English teacher, like mine, made you read it?

[B]

But the point is that Shakespeare's metaphor wasn't mixed.

[A]

No.

[B]

Taking up arms for revenge is futile. It's self destructive.

[A]

Right.

[B]

Just like taking as choosing not to be.

[A]

Right, Right. Right.

[B]

So when he's saying to be or not to be. Right. He is not just talking about suicide, he's also foreshadowing how the revenge is gonna go.

[A]

Right.

[B]

He's gonna choose not to be by pursuing the path of revenge, which is futile, self destructive, and results in his own death.

[A]

Right.

[B]

This is how every word in that famous speech drives the message home.

[A]

Right. And that was only like, what, four lines? That was.

[B]

Right.

[A]

That was like woof. And that was already, what, five minutes of climbing. That is the level of depth that he and Taylor both get into.

[B]

Right. And we talked last week, episode three on All Too well, we did, and saw that from the very first words, they're all chosen by design. Even when she makes a casual remark, when she says, when the scarf reminds you of innocence and it smells like me, even those words are chosen specifically.

[A]

And multiple allusions are happening. I mean, alluding to smells like, Teen Spirit alluding to, you know, smell kind of like.

[B]

And the innocence being the metaphor for the scarf. So the point is, when you listen to. When you read any great work of literature or a great songwriter like Taylor, and if you don't think you understand a word, that's probably because you don't understand what the author is trying to communicate.

[A]

Right. And it's always possible to understand. And that's what we want to help people do.

[B]

Yeah. So let's go to the song itself. This is a great song. This is, I think, one of her most ingenious songs.

[A]

Yes. He loves it a lot. I like it too. I think it's a quite good song.

[B]

And so it's called, the title is Mastermind. And it begins. You want to start.

[A]

Once upon a time, the planets and the fates and all the stars aligned. You and I ended up in the same room at the same time. And that was beautiful. Do you want me to keep reading?

[B]

You can go on. Yeah.

[A]

And the touch of a hand lit the fuse of a chain reaction of counter moves to assess the equation of you. Checkmate. I couldn't lose.

[B]

So let's pause here for a second.

[A]

Snaps.

[B]

So she begins. Once Upon a Time, she does.

[A]

Which, as we've already spoken about, she.

[B]

Has used twice before as the opening of a song.

[A]

Yes. In Dear John. And. And I knew you were not Dear John. No. What's his face? Oh, Forever and always.

[B]

Yes.

[A]

Yeah.

[B]

And as we discussed in episode one, it's how she begins. I knew you were trouble. Once upon a time. A few mistakes ago. So it's not a casual. She's not being casual.

[A]

No. Because whenever she uses Once Upon a Time, it's always steeped in irony. It's always very sarcastic.

[B]

So we know this song's gonna be about irony. There's gonna be a lot of irony going on in this song.

[A]

Right.

[B]

And we'll come back to, I think.

[A]

Uh, oh, the popo's here. They know what you did.

[B]

I'm just gonna let that pass. Going in the other direction. Safe for now. So let's. To understand exactly why she does that, we're gonna have to go a little further, but I want to talk about these lines a little bit. So in here, she's saying that she's in the same room with this guy.

[A]

Yeah.

[B]

And then she touches her hand, and then there's this chain reaction. And then there's Equation and Checkmate and she couldn't lose. And then she says, what if I told you none of it was accidental? And the first night that you saw me Nothing was gonna stop me I laid the groundwork and then just like clockwork the dominoes cascaded into line in a line. What if I told you I'm a mastermind and now you're mine? It was all by design because I'm a mastermind.

[A]

Yeah.

[B]

So what Taylor is saying here is that this opening was a bit of a faint. We will soon learn that this song is actually a confession she is making to this young man.

[A]

Yeah, well, and when she was just with Jack Antonoff, apparently she wanted it to sound in the beginning, kind of like there was like a hero, a princess, that she was kind of talking. It was nice. And then towards the chorus, you want to sound like the villain had just entered and it was confessional.

[B]

Yes. You can find online her describing that she's very proud of this song and she wanted. She says we wanted the verse to sound like romance and this sort of heroes type of soundtrack. And then we wanted the chorus to sound like a villain has just entered the room. And the idea that you're flipping the narrative and you've been planning and plotting things and making this look like an accident, okay. And she says, I think that's sort of an inside joke between me and my fans that I tend to do that. And this song is the romantic version of that, right? So again, this gets back to the hero's journey, right? She says, I want to make it so this opening. The planets and the fates and the stars all aligned, right? Got you in the same room at the same time. She's making it seem like, oh, this is just a meet cute. Totally accidental. Just fate, right? And the key line here, the planets and the fates and all the stars aligned, right? Because that goes back to the famous Romeo and Juliet, the story of the star crossed lovers, a play that she wrote, writes a whole song about.

[A]

She does Romeo, take me.

[B]

So the point is, in the beginning, she's trying to make like, oh, this is just, you know, the planets and this is a very romantic, you know, hero's journey type thing, right? And then.

[A]

Well, she's also playing on the whole idea of the. Of the validity of the hero's journey in itself because she's kind of saying, like by putting all of these things, all these tropes of these examples of perfect hero's journey, a perfect love stories, that really she was behind it all. She's kind of saying that there's no such thing as a perfect love story because there's always.

[B]

You have to tr. You have to put in effort.

[A]

You do.

[B]

But now we can understand why she said once upon a time and why she hearkened back to I knew you were trouble. So let me play the opening.

[A]

Sure. Hearken. Harken is a good word.

[B]

I knew you were trouble.

[A]

Once upon a time. A few mistakes ago. I was in your sight. You got me alone. You found me. You found me. You found me. So he found her, right?

[B]

Once upon. So I was in your sights. Yeah, you got me alone, you found me.

[A]

It's kind of the exact opposite.

[B]

It's this reversed story here. Once upon a time, you and I ended up in the same room at the same time.

[A]

Pretty clever of her, I guess.

[B]

But it wasn't accidental. Nothing was going to stop me. It's the reverse story.

[A]

And in the one song where she talks about it not being an accident, she also, not on accident, uses the exact opening line for the very reverse story, right?

[B]

So this is how she writes songs.

[A]

Yeah.

[B]

And the point is, from the very first line, we want to head towards the very end. We still know there's gonna be an ironic twist. Of course, we don't know what it is, which is the point. Right. We just know it's coming. So this is how she's laid out this song. And then she gets into this. A series of wild statements. Some of the most honest statements she ever made.

[A]

In fact, other than an antihero. This whole album, Midnight's as a whole is a very honest album.

[B]

And there's. This song is clearly a pair with antihero.

[A]

Yeah.

[B]

Because she is making confessions. And as we'll see, they're very similar confessions. Not exactly the same.

[A]

Yeah.

[B]

So why don't you take us to the next.

[A]

You do the thing. Yeah, I'll do the thing.

[B]

From the chorus from uc. Yeah.

[A]

Oh, this is the verse.

[B]

Yeah, the verse.

[A]

Terminology. No, it's okay. You see, all the wisest women had to do it this way. Because we were born to be the pawn in every lover's game. If you fail to plan, you plan to fail. Now this is bolded on my sheets. We're going to get to this strategy sets the scene for the tale. I'm the wind in our free flowing sails and the liquor in our cocktails. So snaps, snaps.

[B]

This is. This is. She is now saying that she's not just the mastermind who does things by design, she's saying all the wisest women had to do the same. The same way.

[A]

Right, right.

[B]

So.

[A]

And there is, you know, there is a huge element of. Sorry, he's pointing at me. Yes, of course. You know, as the designated woman in this room, one of us is, I feel very. Yes. Is a very male dominated space. And I have to take back my power in this room. And as a woman who is taking back her power, I must say that it's true that you tend to get the feeling, and maybe it's just because I go to an all girls school, that I don't really feel the presence of men much in my life. But when I am around men, I do notice that it's quite hard to feel like, for lack of a better term, you are the alpha. In fact, you're not. It feels like conversations are very, you know, controlled by men. I don't know. There's this feeling that the decisions ultimately will be made by men.

[B]

And let me say, you know, so you know that.

[A]

Well, yes. The other quote that I think of is, behind every great man, there's A woman. And that's because the only way that women in the past have been able to exert power and decision making is from behind the scenes by pulling the strings. Because if they're out in the open, people will judge them. So you have to kind of find a way to be a little sneaky about it. And that's what I think. I mean I think a lot of the benefit, not to plug all girls schools, but a lot of the benefit of all girls schools is you get to be out in the open, you get to have an opinion and perhaps later in life you're better at being behind the scenes. And well, that was one of the.

[B]

Reasons we sent you.

[A]

I'm going to a co ed college now. Woof. But the point is.

[B]

Well, let me, let me say.

[A]

Yeah, sure, man. Interrupt me.

[B]

Well, no, what I'm here to say is that, that historically the men made the rules.

[A]

Yeah.

[B]

And what Taylor is saying, that male.

[A]

Ally over here getting line women.

[B]

In a world where the patriarchy is making the rules.

[A]

Yeah.

[B]

Then women have to be calculating, quote unquote, calculating because they're going to have to figure out how to get what they want within these rules.

[A]

Right.

[B]

And you know, it's, it's. And this song is clearly a statement of Taylor reclaiming her power.

[A]

Right?

[B]

Right. And she said so there's this other quote in the time in Time magazine, she was named person of the year 2023.

[A]

Right.

[B]

And she said when she's talking about this song, I thought wouldn't it be fun to have a lyric about being calculated? She pauses. It's quote. It's something that's been thrown at me like a dagger. But now I take it as a compliment. Right. She has been accused of being calculating. Hopefully that's not a shock to anybody.

[A]

This is her realizing that like yeah, she was calculating and now she's a friggin billionaire who just bought back all her songs. Like I mean at the time of recording, literally it's been like what, a week since she bought them back? A few days.

[B]

We're recording this about a week or a week after that. And this is also she's mentioned to assess the equation of. She mentions checkmate and women are just a pawn.

[A]

Right, Right.

[B]

So she's referencing an earlier.

[A]

So she is.

[B]

When she was 19.

[A]

19.

[B]

And she tragically went out with a guy her friends told her not to.

[A]

Oh my God.

[B]

The worst of the worst. John Mayer.

[A]

Oh wow.

[B]

Google him, ladies.

[A]

Yeah. Be afraid.

[B]

That song, Dear John, she says among it's a brutal Song. I'm sure it's very well deserved given who it was.

[A]

Right.

[B]

But one of the lyrics is, and I lived in your chess game, but you changed the rules every day.

[A]

See, that must be frustrating, because when I was learning how to play chess, I mean, like, honestly, I could barely grasp the rules.

[B]

It would be very hard to learn chess if the rules changed every single time we played it.

[A]

Yeah, we played no stress chess. Do you remember that? You taught me how to play chess.

[B]

Do we got the no stress chess?

[A]

This sounds like stress chess, guys.

[B]

Yes. This is the most. This is the reverse of that. But the point is, is in this song, Taylor's not 19 anymore.

[A]

Ew.

[B]

She is a very grown woman, and she is saying, hey, I'm doing the checkmates here.

[A]

Right? So this whole perspective of feminism that. That says, you know, take this stuff as a compliment. It's called, like, lean in feminism. This whole kind of, you know, not to go all woke on you guys. But this whole. It is true that this whole kind of perspective on feminism is still coming from a place of privilege because it's easier, especially for if you're. It's hard to get around men in power if you don't have some privilege already. It's important to note that she has been criticized a little bit for this, but. Right.

[B]

Well, I think. Let me say that, yes. She's been accused of being calculating.

[A]

Yeah.

[B]

Very calculating career. And I would just say they don't use those words about any man.

[A]

Right.

[B]

I don't know that I've ever heard a man accused of being calculating.

[A]

And, I mean, it's hard because she probably is just.

[B]

There's a point I want to make.

[A]

Yeah. All right. You make your point, man.

[B]

I studied a lot of interrupting me songs. Yeah, well, you interrupted me first.

[A]

Yeah, but I'm a woman, so I can interrupt people. Hashtag slay, hashtag take back the power, Hashtag double standard. Double standard. This is the triple standard. And the triple. It cancels out.

[B]

But my point is this. You cannot be a pop songwriter if you're not calculating. Pop songs are the most calculated thing that there is. There's like a four. There is a formula that she follows all the time. Now, she subverts it in the context of the structure that she has to use. But everybody does it. I mean, there's only a very rare few songs that blow up the structure, like, let's say, Bohemian Rhapsody.

[A]

Right.

[B]

But 99.9% of hit songs follow this formula.

[A]

I mean, literally 99.9.

[B]

So it is in my mind, absurd to accuse a great songwriter. You wouldn't say Lennon McCartney were calculating. You would just say they're great songwriters. Right. It would never occur to you. So I think. I do think that it is absurd. And to this question of privilege.

[A]

Right.

[B]

Comes the bridge.

[A]

Comes the bridge.

[B]

The bridge is always where she amps up the hyperbole. She takes things to another level.

[A]

Yeah.

[B]

What's the bridge in this song?

[A]

No one wanted to play with me as a little kid, so I've been scheming like a criminal ever since to make them love me and make it seem effortless. This is the first time I've felt the need to confess. And I swear I'm only cryptic and Machiavelli. Whoa. I'm literally Italian. That was kind of a hate crime. I'm only cryptic and Machiavellian because I care.

[B]

Wow.

[A]

Yeah.

[B]

As bridges go, it's a great bridge. It is a jaw dropper.

[A]

Yeah.

[B]

No one wanted to play with me as a little kid.

[A]

I mean, that's not true, because we know she had a best friend, but we do.

[B]

There is this story about how she wanted to go to the mall, and then she called up her friends to go to the mall, and her friends say, no, we're not going to the mall.

[A]

Going to the mall.

[B]

So her mother takes her to the mall, and lo and behold, all her friends are there.

[A]

Wait, actually, because that's kind of, like, devious.

[B]

Yeah.

[A]

Like, I kind of hate that.

[B]

I just was reading that.

[A]

Like, if that happened to me, like, you have to believe that I would literally go up to my friends and bitch slab every single one of them.

[B]

Well, apparently, how the story went is that her mom took her to the better mall. The one that's a little farther away.

[A]

Yeah. Like Tyson's two.

[B]

Yes.

[A]

Not Tyson's one.

[B]

Exactly.

[A]

That's a little Northern Virginia.

[B]

But the point is, in this telling of the story, she's a sad little kid, and so she's lonely, so she has to use her brain.

[A]

Yeah, Amen, sister.

[B]

To figure out how to scheme like a criminal ever since. Another interesting choice of words, because she's not. The first time she's called herself a criminal.

[A]

No, no.

[B]

I mean, in getaway car. Right. The whole damn song.

[A]

It's about being a criminal and being Bonnie and Bonnie and Clyde fresh out the slammer. Another one where she compares herself to.

[B]

Crime and also the word scheming.

[A]

Scheming.

[B]

Because scheming is the word that she uses in she's scheming antihero.

[A]

She Does.

[B]

Right. She says she's afraid that she's going to be scheming so much, you're going to leave.

[A]

Yeah.

[B]

So scheming, of course, is part of doing. Being Machiavellian.

[A]

Sure.

[B]

And so this is very interesting part.

[A]

Of being an antihero. Right. But Taylor is also known for her empathy. Right. She, as we mentioned in one of the episodes before, is she writes songs about, you know, states that of which she has never experienced. Right. Like, this is me trying. Even this song, we know that people probably wanted to play with her as a kid.

[B]

This is a poem she's, you know, not. This is a hyperbolic, hyperbole version.

[A]

Right.

[B]

She is. But. But one of the things she's doing is she saying to her critics. Because this song isn't just addressed to her fans, and it's not just addressed to. I've gotta write a great song for the general public. No, this song is clearly written at those critics who have been calling her calculating, in which she's saying, you call me Calculating, I'm gonna amp that up to the level of 11.

[A]

Yeah, bitch, I've been calculating. What about it?

[B]

That's what she does in blank space, by the way. Very similar idea. It's similar. You will spell something. I'm going to own it and take.

[A]

It to the next level. And we love that for her.

[B]

And this great line, of course, I swear I'm only cryptic in Machiavellian because.

[A]

I swear, it's like hair.

[B]

Right. And we have seen she is cryptic. Right. I mean, like said when she. When you first hear. See the line, once upon a time, you know, it's a reference to her. To her earlier song, but you don't know what it's true.

[A]

And the whole phrase, once upon a time is cryptic in and of itself.

[B]

By design.

[A]

By design.

[B]

It's some imaginary time.

[A]

Some imaginary time, Yeah. A long time ago, there's a fairy.

[B]

Tale that happened and it has a happy ending. Now, the interesting thing is, of the three songs where she says once upon a time, this is the only one that actually has sort of a happy ending.

[A]

It does. Well, you know, I kind of want to talk about the ending and let's. So let me read that. Hashtag. Segue, segue, segue, segue. So I told you that none of it was accidental. The first night that you saw me nothing was gonna stop me. I laid the groundwork and then saw a wide smirk on your face. You knew the entire time, you knew that I'm a mastermind. And now you're mine, yeah, all you did was smile. Cause I'm a mastermind. I don't know why I chose that octave.

[B]

So anyway, wow.

[A]

I mean, this is the twist.

[B]

This is the irony. We were promised.

[A]

I've kind of. And I haven't really told you about this, but I've kind of always had a problem with this ending.

[B]

Okay.

[A]

Not that I. I'm. Listen, I'm glad that she's getting her mans. I'm glad that she's getting her bae. I don't love that she's kind of undermining her entire cold and calculating nature by saying that he knew the entire time because she wasn't really doing a good job if he knew the entire time. I've kind of always had a problem with that because I feel like, yes, it's a good way lyrically to end this song, but I also think that, like, you know, sometimes you don't want men to be clued in on all of your little calculations that you're doing because it kind of, you know, emasculate them. I don't know.

[B]

I mean, I didn't know that this was bothering you all these years.

[A]

All these years. It's been like, two years, but yes. Right.

[B]

Because I would have offered you my theory of why she does that.

[A]

Yes, man. What's your theory?

[B]

My theory is that this is an ingenious ending because what she's saying to all of her critics who accuse her of being calculating is, if I'm so calculating, how do you know that I'm calculating? Apparently, I'm not so calculating that I've been able to fool you.

[A]

So true. That's so true.

[B]

Right?

[A]

Yeah. I've always read it like it was just a straight love song or a song to her fans. But it is true that when you read it like a song to her critics, if you read it holistically, that. That's true. I actually. Actually quite like your interpretation, man.

[B]

Wow. Oh, man. Can we just enjoy this moment for just a few.

[A]

Yes. You get a few points for that. You get a few points.

[B]

Yeah. And look, there's a lot of interpretation to this song.

[A]

Right, Right.

[B]

This song clearly is operating at a lot of levels.

[A]

It is. And that's also part of the genius. Right. You want. Right? Like, I mean, that's. If you're ever writing, like, a speech or something and you have a point in mind that you want to make. But it's also, like, maybe it's for a general audience. Maybe you're a valedictorian giving a Speech. You want it to kind of be general enough that it's like you want. You can give the speech for anyone, but you also want it to be specific. You want it to have kind of these little things that. That multiple people can latch onto. You want to have like, you know, I mean, like you. If you're a great writer, your stories, your speeches will do multiple things at once. Right.

[B]

And they have to be. Right. You want to be both specific and timeless.

[A]

Right, right. And this like 1984. Right. I mean, obviously. Very obviously, in reference to the rise of communists and authoritarianism. But also when you read it, it is kind of, you know, a story about love and. And human nature in the face of.

[B]

What'S going on today.

[A]

Oppression. Right, exactly.

[B]

So this loops back to the very first point. This is the point that we said, if you stuck with us this whole episode, if you did. Yeah. Then you'd see if you want to be able to write a song that delivers multiple meanings.

[A]

Yeah.

[B]

And therefore. And one of the points of delivering multiple meanings is to affect different people differently.

[A]

Yeah.

[B]

And to, you know, have as broad an audience at. At the same time that you can have a specific audience.

[A]

Right, right. Which is what Taylor Swift has done.

[B]

She has created her tribe.

[A]

Yes.

[B]

But she's also at the. Created such a popular movement, and so much so she's able to write a pop song for the general public that her fans can love a particular way.

[A]

It's true.

[B]

At the same time. And at the same time she can also tweak her critics.

[A]

Yeah. Lady Gaga does this too. I think she's another good example.

[B]

I would not want to leave the impression she's the only.

[A]

Oh, no, no, no, no. I'm just saying like. Like there are a few, Few good examples I can think of. Right. Beyonce, her, Lady Gaga. They do a great job of catering not only to their fans, but to the general public. And I. I think. I think it's worth. I think it's worth understanding. Like, same with Shakespeare. Right. His plays are. Are seen by many a children whose parents drag them to them and then maybe they end up liking them. Or many, many parents who. Who sing at them when they're two years old, and then they end up liking them. Just for example, just off the top of my head, just thinking about that.

[B]

Shakespeare wrote to the Groundlings, the people who paid a penny or two and wanted the broad humor, which was like.

[A]

$1,000, like, you know, nowadays.

[B]

And then there were the people in the, you know, the regular seats, which might be the middle Class who are more educated and they wanted more sophistication. Yes. And in fact, like Taylor, Shakespeare was accused of being too popular.

[A]

He was.

[B]

But that's the genius. Can I write art and be popular at the same time? Because there's always been this.

[A]

Well. And does popularity negate the art?

[B]

Right, exactly right. And so the point is, you want to become a better writer. You want to have every word chosen for a purpose. And if you don't know what the purpose is, then get rid of that word.

[A]

Cut it out.

[B]

Cut it out. And this is the secret to writing by design. And also coherently. You have to know the ending that you're going for from the very first word.

[A]

And you can have multiple effects that you're trying to go for, like fans, critics, general audience. But. But make sure that if those are the three, those are the three you're trying to do it, you know, and.

[B]

If you fail to plan, you plan to fail.

[A]

Amen, sister. Amen.

[B]

And this is an empower. This is meant to be an empowering song. Yeah, it is one of her. This is really a classic hero's journey story.

[A]

Yes. I feel empowered. I feel empowered when I listen to. I feel like I'm owning my power. You know, I feel like another plug of all girls schools is when you're doing your work, you do kind of have to be very strategic about, you know, what you include in an essay. It's kind of like, you know, I mean, they teach you this in school, but they're not explicit. It's not just in essays that you have to choose what to include and what to exclude, because you only have a certain amount of time. It's in life. And, you know, this seems like a good segue into maybe a closing wrapping up of this episode. Speaking of school, a bit of homework. If you find yourself writing, writing a speech, trying to communicate with somebody, um, outline a few points that you're trying to make. Outline 1, 1 or 2 or 3 in her case, effects that you're trying to have. And make sure that every single word that you're using, you know, goes to. That does that. That effect is a means to that end and only that end. Yeah.

[B]

And this is clarity of purpose.

[A]

Yes.

[B]

Right. When you want to be. This is the other point. If you want to be a great writer, you're going to have to develop your own voice.

[A]

Right.

[B]

And that voice is going to be this internal consistency. My homework is a follow up on the homework from episode three, the Hero's Journey.

[A]

Well, he actually taught at real colleges. So he's better at giving homework than I am.

[B]

But this is hero's journey story. Right. And it has this key element. No one wanted to play with me as a little kid.

[A]

Yeah. Find people to play with you. That's another thing of homework.

[B]

Well, that's important. This is weird. We do live in a loneliness epidemic.

[A]

It is.

[B]

But the key point here is that she's saying, I didn't start out as a mastermind. That's the point. This is a journey she went through. And when she got through with it, she's now bringing the elixir.

[A]

Elixir.

[B]

Return of the elixir. This is the lesson. This is the. With great power comes great responsibility. But her lesson to you is. Yeah, you need to be strategic. You need to do things by design. And all the wisest women.

[A]

And if any man tries to come for you, just tell them you are owning your power. Amen to that.

[B]

Alrighty.

[A]

And thank you for listening.