Taylor Swift's 'Midnights' as Enneagram Types

"I know the Enneagram is overhyped right now. I don't care. It is fun."

Nov 01, 2022

By Dom

Taylor Swift and some of her friends created an incredible album called “Midnights.” It’s an examination of the thoughts, desires, and fears that keep you up until midnight and beyond.

Before I give an inexplicably unnecessary in-depth analysis of each song and its placement on the Enneagram circle, I understand many of you just want to skim a bulleted list and see if you agree with my assessments.

I, too, have an affinity for skimming.

Here’s my breakdown:

Enneagram Type One: The Reformer

Anti‐Hero
Glitch

Enneagram Type Two: The Helper

Bigger Than the Whole Sky
Dear Reader

Enneagram Type Three: The Achiever

Bejeweled

Enneagram Type Four: The Individualist

Snow on the Beach
Midnight Rain
Sweet Nothing
Would’ve, Could’ve, Should’ve

Enneagram Type Five: The Investigator

You’re on Your Own, Kid
Mastermind

Enneagram Type Six: The Loyalist

Maroon
Karma

Enneagram Type Seven: The Enthusiast

Labyrinth
High Infidelity

Enneagram Type Eight: The Challenger

Vigilante Shit
The Great War

Enneagram Type Nine: The Peacemaker

Lavender Haze
Question…?

Okay, now let’s go a little deeper.

“Midnights” is a concept album about the heavy thoughts that keep you awake at night. Taylor refers to it as “13 songs about 13 sleepless nights.” Plus, we’ve got seven bonus tracks. Someone give Blondie some Melatonin (I’ll take some, too. I’m writing this at 3 a.m.).

Mirroring insomnia itself, the album covers a wide spectrum of experiences — heartbreak, easygoing love, toxic love, self-loathing, self-celebration, grief, late-stage capitalism, crushes, revenge, makeup, and several other essential ingredients of existing as a human.

Do you know what else covers a wide spectrum of human experiences? Say it with me: The Enneagram!

Yes, I know the Enneagram is overhyped right now.

I don’t care.

It is fun.

And it’s a helpful tool for introspection and empathy.

If you’re tired of hearing about the Enneagram, why did you click on this article? Go be curmudgeonly somewhere else! No offense.

Nice. Now that it’s just us people who aren’t afraid to like popular things, let’s pick up where we left off.

What is the Enneagram?

The Enneagram is a system used to describe and categorize personality types, using nine points on a circle — also known as Types. Each Type represents a specific way of thinking, doing, and feeling. The Types are divided and connected in all sorts of ways. Read more about it here.

Contrary to what you might see on your Instagram feed, you’re not supposed to find your number by taking an online quiz or assessment. Rather, you should examine the traits, components, and core motivations of each Type and hypothesize which number resonates with you. Then, as you continue to learn about the Enneagram System, you can confirm or adjust your hypothesis accordingly.

Disclaimer
There’s limited research about the validity of the Enneagram as a personality test. It hasn’t been the subject any major studies, and there are only a handful of peer-reviewed articles. Here’s one!
Admittedly, some of the Ennneagram’s assertions can be a little fluffy (AKA hard to measure scientifically).
But at the same time, I’ve found it eerily accurate at describing my thoughts, feelings, and motivations. If anything, it’s a nice tool for mindfulness and reflection. And it’s just, kind of like, fun.

Okay, let’s examine each “Midnights” track through the lens of the Enneagram.

ENNEAGRAM ONE — THE REFORMER

The Rational, Idealistic Type. Principled, Purposeful, Self-Controlled, and Perfectionistic.

Anti-Hero & Glitch

Anti-Hero

“I’ll stare directly at the sun, but never in the mirror.” — Enneagram Type One

Taylor Alison Swift created an anthem for our self-critical friends: Type Ones, the Reformers, often called The Perfectionists. When you spend your life striving for perfection, a famously unattainable goal, it’s easy to develop an inner voice that says: “you are bad.”

In Anti-Hero, Taylor refers to herself as a monster on a hill, a narcissistic congressman, a problem.

Fortunately, it seems like Taylor is reflecting from a place of growth. Especially when paired with the music video, I believe Taylor has found a way to celebrate all the components of her true self, even the monster on the hill.

Still, I think she needs a hug. Hug her, Joe!

Glitch

“The system’s breaking down.” — Enneagram Type One

In “Glitch,” Taylor is caught off guard when a casual fling (Joe Alwyn [swoon]) transforms into a long-term, safe-and-sound, healthy, equitable relationship.

Oh no, poor Enneagram 1! Your perfect little system and your perfect little plan didn’t go as expected! Oh no! You didn’t add falling in love to your calendar? I’m so sorry. Thoughts and prayers!

Alright, I’m not being fair. I’m doing a bit. This song isn’t actually about being distressed by the plot twist of falling in love with a hot kind-hearted mysterious British guy. Rather, she sings that she’s “not even sorry. Nights are so starry.”

This song ticks me off. I like it so much.

ENNEAGRAM TWO — THE HELPER

The Caring, Interpersonal Type. Demonstrative, Generous, People-Pleasing, and Possessive.

Bigger Than the Whole Sky & Dear Reader

Bigger Than The Whole Sky

“And I’ve got a lot to pine about, I’ve got a lot to live without.” — Enneagram Type Two

Enneagram Twos — the Helpers. The Caretakers. They show their love by giving their time, caring for your needs, and just showing up. They also have a giant capacity to feel and an infinitely expansive desire to be loved.

This song is heartbreaking.

Some people interpret it as a breakup song, and others feel like it’s a song about grief.

In “Miscarriage Is a Thief,” Liz Kadar shares how this song resonated with her throughout her grieving process. It’s a gut-wrenchingly vulnerable story — read it if you can.

I’m not sure who or what inspired Taylor to write “Bigger Than The Whole Sky.” Regardless, it explores the feeling of losing the opportunity to give somebody love. It breaks my heart. But I’m glad it’s helping people process their pain. ❤

Dear Reader

“Dear reader, you don’t have to answer, just ’cause they asked you.” — Enneagram Type Two

Taylor wrote a letter to her readers (us), offering first-hand insights she’s gathered from going through the wringer. And then, she’s like: “don’t listen to me because what do I know?”

Wait a minute Taylor, you dropped some helpful advice in this song. “If it feels like a trap, you’re already in one.” This is a great reminder to stop effing with people who make you feel stressed and anxious. Super helpful. Helpful! The Helper! Enneagram Two!

Thanks for looking out for us, Taylor. Take a break, though! Go off the grid for a few years. I’ll look after Joe while you’re gone.

ENNEAGRAM THREE — THE ACHIEVER/THE PERFORMER

The Success-Oriented, Pragmatic Type: Adaptive, Excelling, Driven, and Image-Conscious.

Bejeweled

“I can still make the whole place shimmer.” — Enneagram Type Three

Type Threes are alluring, charming, and hyper-aware of their image.

In “Bejeweled,” Taylor reflects on a relationship that didn’t give her enough space to shine bright like a diamond (which reminds me — new Rihanna music, yay!).

Anyways, she breaks up with the vibe-killing-style-cramper and then transcends into her “This Little Light of Mine, I’m Gonna Let it Shine” Era (which reminds me of this incredible scene from the Fresh Prince of Bel-Air).

Bejeweled feels like a redemption song from the heartbreak Taylor sings about in “Dear John.” In the iconic, anger-infused break-up ballad, Taylor calls out a manipulative guy for leaving a wake of destruction throughout his serial dating habits.

She sings, “all the girls that you’ve run dry have tired, lifeless eyes because you burned them out.”

But this time around, Jonathan Mayer (or whoever) didn’t steal no glimmer from NOBODY. The girls are out and about, painting the town with glitter, Johnny!

Also, the music video is so good. Laura Dern should get an entire EGOT for her performance. Performance! Performer! Enneagram Three!

ENNEAGRAM FOUR — THE INDIVIDUALIST

The Sensitive, Withdrawn Type. Expressive, Dramatic, Self-Absorbed, and Temperamental.

Snow on the Beach, Midnight Rain, Sweet Nothing, & Would’ve, Could’ve, Should’ve

Snow On The Beach

“Are we falling like snow at the beach? Weird, but fuckin’ beautiful.” — Enneagram Type Four

Four Types, in my opinion, are the most mysterious humans and the most difficult to describe. Often called “The Individualist” or “The Romantic,” they spend a lot of time daydreaming and imagining how it would feel if someone understood their complex, ever-changing emotions.

“Snow On the Beach,” tells the story of two people falling in love with each other at the exact same time — a phenomenon that Taylor calls “cataclysmic” and “fated.”

Rare, good, and (fucking) beautiful. Like snow on the beach.

Midnight Rain

“He wanted a bride, I was making my own name.” — Enneagram Type Four

This one’s pretty easy. As we’ve discussed, Fours value their independence. They don’t want to lose their identity and individuality.

In “Midnight Rain,” we see a relationship end because Taylor slowly starts to lose her sense of self. While she cares about the relationship, she can’t edit herself down enough to fit inside its box.

Sweet Nothing

“Outside, they’re push and shoving. You’re in the kitchen humming. All that you ever wanted from me was nothing.” — Enneagram Type Four

A Four wants to be awestruck. A Four is afraid they might not find someone that understands their beautiful brain. A Four is searching for beauty in everyday life. “Sweet Nothing” beautifully describes the bliss of finding all these things.

Sit back, relax, and bask in the gratitude of living with someone that humors your musings with quiet contentment, hums in the kitchen, and puts pebbles in his pocket to remind him of the good fugging time you at the beach. Perhaps a snowy beach.

Would’ve, Could’ve, Should’ve

“Stained glass windows in my mind. I regret you all the time.” — Enneagram Type Four

Swift writes about a bad breakup she experience when she was only 19 years old. AKA, she’s reflecting on a broken heart from over a decade ago. It must’ve stung.

In the song, she oscillates between regret, anger, sadness, and hope.

“Would’ve, Could’ve, Should’ve” sits squarely in Enneagram Four territory for a few reasons. The painful pondering. The vast range of emotions. And maybe, most pointedly: “Oh, God rest my soul, I miss who I used to be.”

She lost a part of herself in the relationship — and 10 years later, she’s still trying to get it back.

John Mayer, say sorry! And you too, Jake!

ENNEAGRAM FIVE — THE INVESTIGATOR

The Intense, Cerebral Type: Perceptive, Innovative, Secretive, and Isolated.

You’re On Your Own, Kid & Mastermind

You’re On Your Own, Kid

“I wait patiently, he’s gonna notice me.” — Enneagram Type Five

Here, we have a tough exploration of semi-requited love. In “You’re On Your Own, Kid,” I see a Type Five who let their guard down and invited someone into their lonely little corner.

Taylor gets comfortable with the discomfort of letting someone into her space. “Maybe, I’m not on my own,” I imagine her saying. Nice. :)

But then… The. Jerk. Didn’t. Show. Up. To. Her. 21st. Birthday. Party.

Mastermind

“It was all by design because I’m a mastermind.” — Enneagram Type Five

Enneagram Fives — the Investigators. AKA the Observers. Watching, painstakingly analyzing details, and collecting information.

Some Enneagram teachers say Fives have an almost magical ability to power conjure up a cloak of invisibility when they don’t want to be perceived. They lurk until they’re ready to be seen.

This song is a unique POV on the typical Five experience because it tells the story of a person who thinks they’re scheming in the shadows.

Seemingly, it follows Taylor as she tries to orchestrate an elaborate plan to win the attention of a prospective love interest (Joey Alywn).

But she’s not as sneaky as she thinks. She concedes: “I laid the groundwork. And then saw a wide smirk on your face, you knew the entire time.”

Haha! Not so stealthy, are you, Tayla?

ENNEAGRAM SIX — THE LOYALIST

The Committed, Security-Oriented Type: Engaging, Responsible, Anxious, and Suspicious.

Maroon & Karma

Maroon

The lips I used to call home.” — Enneagram Type Six

Woah, what a great song. In the first verse, Taylor uses “Maroon” to describe a whole bunch of cute and good things that happened during the early stages of her relationship. Love bites, red wine, blushing.

But things switch up in the second verse. Her cheeks aren’t blushing because she’s feeling the passion. But they're turning maroon with anger.

This song feels like a Six’s worst fear. Loyalty, intimacy, and security are replaced by resentment, distance, and soured memories.

Karma

“Karma’s gonna track you down.” — Enneagram Type Six

I debated putting this song in the Enneagram 8 section, but I think it fits better with the Sixes. Fun fact, there are two types of Sixes: Phobic and Counter-Phobic.

Phobic Sixes seek out security through structure and cleary-defined relationships.

Counter-Phobic Sixes seek out security by dismantling systems of injustice and knocking down people who abuse their power. They don’t eff with corrupt leaders or exploitative dumb dumbs.

In “Karma,” Taylor Swift celebrates her clean conscious and taunts her enemies for their incoming Karmic justice. This song is so satisfying.

Do you agree, Scooter?

ENNEAGRAM SEVEN — THE ENTHUSIAST

The Busy, Fun-Loving Type: Spontaneous, Versatile, Distractible, and Scattered.

Labyrinth & High Infidelity

Labyrinth

“You would break your back to make me break a smile.” — Enneagram Type Seven

From my interpretation, Labyrinth follows a relationship that was heading for impending doom — but miraculously, things take a happy turn. Taylor thinks, “the plane is going down.”

But just in the nick of time, a hot metaphorical pilot (tall, British, mysterious, rich) turns the metaphorical 747 around.

One lyric, in particular, solidifies this as an Enneagram 7’s dream: “You would break your back to make me break a smile.”

Sevens are committed to chasing away the bad feelings — for themselves and for others.

In this song, I hear two Sevens in love. They embrace the discomfort of being afraid and excited at the same time. They sense each other’s discomfort to replace it with good vibes. How cute!

High Infidelity

“Do you really wanna know where I was April 29th? Do I really have to chart the constellations in his eyes?” — Enneagram Type Seven

High Infidelity depicts a relationship riddled with conflict, resentment, passive aggression, emotional unavailability, and perhaps too many metaphors.

The narrator (Taylor?) is all like: “I’m tired of not having fun and not being happy, not being in love — so I’m going to [redacted] with [redacted].”

Then her partner (“C*lvin H*rris?) is all like, “Sorry, what were you saying I wasn’t listening?”

Facing an emotionally distant lover, living in a house with a boring picket fence, our narrator did—in fact—decide to [redacted] with [redacted]. And then maybe regrets it?

Anyways, I’m getting too caught up in the lyrical analysis. Big picture, the song follows someone seeking out adventure and pleasure when her life becomes dull.

I love this song because it’s unclear if the speaker (Taylor???) is apologizing, offering an explanation, or simply say saying, “you had it coming.”

We love an ambiguous queen.

ENNEAGRAM EIGHT—THE CHALLENGER

The Powerful, Dominating Type: Self-Confident, Decisive, Willful, and Confrontational.

Labyrinth & High Infidelity

Vigilante Shit

“Whilee was doing lines and crossing all of mine, someone told his white-collar crimes to the FBI.” — Enneagram Type Eight 🤷

Ah, Enneagram 8. The Challenger. Sometimes called The Boss.

Eights make their presence known. They speak truth to power. They get shit done. They don’t let themselves get got. And in the face of injustice, they do stuff.

In “Vigilante Shit,” Taylor Swift does vigilante shit.

While she’s driven by intense anger to commit revenge against some Corporate Chad, her personal grudge has evolved into a mission to serve Chad the justice he deserves while wearing incredible outfits.

Even though this song is currently at the top of my “On Repeat” Spotify Playlist, I completely missed the fact that it’s probably about Taylor Swift telling Scooter Braun’s wife about his extracurricular activities.

Shout out to my friend and nemesis, Samirah, for getting me up to speed.

The Great War

“My knuckles were bruised like violets, sucker punching walls.” — Enneagram Type Eight

Enneagram Eight, obviously.

ENNEAGRAM 9 — THE PEACEMAKER

The Easygoing, Self-Effacing Type: Receptive, Reassuring, Agreeable, and Complacent.

Lavender Haze & Question…?

Lavender Haze

“They’re bringing up my history. But you weren’t even listening.” — Enneagram Type Nine

Perpetually unbothered, Nines tend to distance themselves from conflict. A Nine’s core motivation is to cultivate peace and harmony.

I imagine “Lavender Haze” as a love song between two Nines.

Taylor says “nope” to the dizzying life of deadlines and headlines and embraces an almost-tangible peace. In response, her lover (tall, blonde, British, rich Joe) is either uninterested or oblivious to the news cycles, gossip, and general chaos that surrounds their lives. THAT IS SO HOT TO ME.

This relationship sounds like a steadfast, permanent, built-in oasis from the chaos. An Enneagram Nine’s dream.1

Question…?

“Did you wish you’d put up more of a fight when she said it was too much?” — Enneagram Type Nine

Always hesitant to rock the boat, Enneagram Nines can find it challenging to state their needs or ask for what they want.

They talk in circles and dance around what they’re actually trying to say, hoping you’ll read between the lines and give them what they want.

In “Question…,” Taylor gets so close to asking for what she wants. SO CLOSE. But then, after laying it all out there, she frames her questions as hypothetical, casual small talk.

This song can basically be summed up as: “H-hey. Just out of curiosity, I was just wondering if you might happen to miss anyone that you used to be in love with. And do you, like, want to get back together with them and start a life together? And if so, is that person, like, me? Just kidding lol are you caught up on Succession?”

(I really, really like this song, by the way).

Alright, that’s it for now!

Do you agree with my categorization? Disagree?

While I’m a conflict-avoidant Enneagram Nine, that doesn’t apply to conversations about Taylor Swift. I’ve deadass screamed at a coworker in the breakroom because he told me Taylor Swift was annoying and had too many ex-boyfriends. So on that note, let me know your thoughts. 😊