12 min read

Taylor Swift :: An Empire Built on Empathy

One person has unequivocally been a leader on the intersection of music, business, and technology since I started my career. Here's how her empire is built on empathy.
Taylor Swift :: An Empire Built on Empathy

I've been involved with the intersection of music, business, and technology since always, and formally joined these industries in 2014. Unequivocally in that time a single individual has mastered the intersection of these three disciplines. She has impacted how tech companies deal with artists, how the music business structures deals – and other artists use her way of doing things as template for their own careers. The guiding light in her decision making seems to be empathetic insight into her own audience, and giving them what they want.

Yet, not everyone sees it from this perspective – and if the subject ever gets brought up to me directly, it's normally with a cautious:
"so, what is with the Taylor Swift thing?".

So here it is. I recorded this episode for Myke Hurley's podcast mentorship group outlining how Taylor Swift built her empire on empathy. Here is the script as an essay. You can find referenced media at the bottom.

Growing up in Iceland, I was only vaguely aware of her as being super-surprised at winning awards all the time. Then one day I fell down an Taylor-on-Ellen rabbit-hole at one point and I remember thinking GAADDAMN is this girl charming immediately followed by: I really wish I liked country because she seems cool but hey. not my genre.

And then I Knew You Were Trouble came out.

and I was just like: yeaaah.
I get it.
I get the Taylor Swift thing.

This was also right around the time I was getting my first professional job, at a music/tech company. Our job was to streamline artists selling more tickets to their shows, and spoiler alert, you do it with good marketing. So I'm tuned into the industry, always looking for examples of well-executed campaigns to use as reference materials: and then Taylor Swift promotes her pop album with an op-ed in the Wall Street Journal.

For Taylor Swift, the Future of Music Is a Love Story
The singer and songwriter says artists will still form deep bonds with fans, but the way they do it will change.

The 1989 era is upon us, the year I am also born, and from my perspective it was a MASTERCLASS in brand positioning, media strategy, social media, and she just ascends to this stratosphere executing a perfect strategy right in front of my eyes.

I later learned that literally every aspect of her work has the same meticulous attention to detail: her songwriting, the structure of her live shows, there's a commitment to excellence on every single level. I didn't know that then, I was just focused on the strategy and I was blown away.


I feel like I often hear the success of artists attributed to some genius masterminds at a label – and granted, they are often very effective at amplifying talented people. But it was immediately clear to me that she was at the steering wheel.

the letter can be read in full here

It was obvious to me because, there is no play-book in the office of a label that tells you to write an open letter to Apple because artists aren't fairly compensated on their newly launched music service – or re-record your entire catalogue. Or if there was a sales strategy they could deploy to secure over 1 million in album sales three cycles in a row, why wouldn't they use it for every artist?

Yet it seems with every triumph of Taylor’s, there’s a backlash to follow. It’s even hard for me sometimes to fathom why she’s so controversial, she seems pretty traditional to me –yet there she is, time and time again, up against the 'she can't do that' of the day, week, month or even year. What all this resistance has in common, is that it gets addressed by Taylor herself.

There’s not a press release published by a manager.
– She sang on stage why you gotta be so mean at the Grammys, after a critic who slammed her for a previous vocal performance.
– She directly addresses the whole snake thing in the most obnoxious way possible with giant inflatable snakes on the reputation stage;
– she was super upset for not winning a Grammy for RED so she went home as it wasn’t considered ‘cohesive enough’ and wrote 1989 - an album the NY Times say:

"But by making pop with almost no contemporary references, Ms. Swift is aiming somewhere even higher, a mode of timelessness that few true pop stars even bother aspiring to."

which is a longer way to say: it's cohesive.


The only reason she’d address all the 'Taylor can't do that'-s is because she cares. She cares so much. The mind that can write lyrics capturing ephemeral experiences of falling for someone is also one that can read the mood of the day on the feeds. She uses her insights to inform industry-shaking moves that then become template: like when she wiped her socials.

It's also what makes her such a fan-favourite. She intuitively gets what they want from her. Her two absolute biggest strengths, the songwriting and the strategy come from the same place, of her always having an ear to the ground. It’s a running joke in her fan-community – ’taylurking’ they call it. Another way to put that is to say is because of her empathy, she listens.

On this empathy, she builds her stories. The stories in her songs. Stories for the media; even the story of her own celebrity. And she knows it’s her storytelling that sets her apart. That’s what made Taylor Swift, she doesn’t have the voice of Ariana Grande or the dance moves of Beyoncé - it’s her writing that brought her to the highest echelons, everything else she’s had to catch up on.

It does come with a downside, and it's a dark one. There's no way of being this perceptive to your image and what is being said about you without being incredibly unguarded against criticism. Especially when the criticism is valid. She internalises them, and I’m guessing harshly which is why it comes out in her work so strongly.

She feels them from within. It must be devastating.

She gets that her vocals weren’t strong enough and works on that.
She gets that the only way out of being cancelled is owning the persona you’re being painted out to be, to make it so extreme that anyone who’ll give it a close listen realises it’s satire. To parody her own image.

Empathy – this quality of hers that made her into an icon also means she was insecure this whole way through. She was people-pleasing. In an old journal entry she wrote:

"Criticism of my performance has been the biggest source of pain in my life. I sometimes feel like my college degree is in acting like I'm okay when I'm not.”

In the Miss Americana movie she says outright that people in her line of work who live to twirl for an applause are intrinsically insecure. And so with that, very successfully as we know, she built up her entire belief system around this external validation.

And then overnight, it was gone.

#TaylorSwiftIsOverParty 🐍

"the reason that backlash hurt so much was
that's all I had",

she adds.

She’s forced into letting go of this perfect image it took her a life-time to craft. It was brutal. And I think it transcends being about just her. For a while now, we’ve been immersed in body positivity movements and #metoo – so I think we forget sometimes how everything when we were growing up was just... kinda plastic.

We were told our status comes from how beautiful we are, and when we were growing up that meant being skinny beyond what is good for you. We were 28 when #metoo trended – after many of us carried that type of burden alone for years. All while constantly being told success is what defines you.  And then Taylor, like many, is rudely awakened by the fact that not eating is bad for you, and presenting perfection 24/7 isn't a way to fulfilment as you then never let anyone in.

 It's theater.
 And that's what she got called on.
 and it hurt
 because it was true.

Through her obsession with external validation, she made 1989: the perfect embodiment of everything we’re told to go after. And I think this worldview she’d put everything into achieving crumbled as she accepted her 2nd AOTY, recognising that’s all she ever wanted, and then realising she has no one to call.

Taylor Swift accepts her second 'Album of the Year' award at the 2016 Grammys, possibly the most prestigious honour in all of music 

And I don’t think you need to be this level of celebrity to be fuelled by something so unhealthy, toxic even. I think any one of us who use say, Instagram – if we’re honest with ourselves – might recognise what we’re presenting there is hollow.

I think the story of Taylor Swift is that story, and it’s the story of this time period.

Because she so clearly wants to do a good job and to be liked it’s made it easy to criticise every little misstep.

“If you’re so perfect, explain this”. A person who is not as genuine or good-natured doesn’t get criticism like that, because no one holds them to that standard.

I’m not defending Taylor Swift for being late to speak up politically. I’m saying she’s not the only one. I know many, in particular young women, who fear it may have an impact on their careers or even dating prospects and social standing to voice their opinion. We’re taught to avoid confrontation and topics like religion, politics and anything else divisive or unlikeable – as of course is the greatest sin of our kind, being unlikeable.

David Letterman pushes Taylor Swift on her political views during her 'RED' campaing in 2012. When she replies: "It's my right to vote, but it's not my right to tell other people what to do" he fistbumps her with a: "Right there, sister"

The most shocking moment to me in the Miss Americana film wasn't when Kanye West had his entire arena of fans start jumping up and down shouting "fuck Taylor Swift"; it was when David Letterman fist-bumps her, for not speaking her mind.  what it says is:
→ look pretty, sing pretty, don't dare challenge us.

A nice girl doesn't make people feel
uncomfortable with her views.

I was so obsessed
with not getting in trouble,
that I was like:

"I'm just not gonna do anything
that anyone could say anything about."
– from the Miss Americana movie

And my question is: how many young girls saw that? How many young girls took that to mean their only worth was beauty and to never say anything up­setting, living on 600 calories a day – quietly carrying the injustices we all know now were rampant at the time.

we’d do as we were told for the most part,
even when what we were told was detrimental to our well-being.

When your number one goal is to be liked, you're putting the power of your well-being in the hands of others.

She’s not the only one who showed early potential, got praise for it and then had her entire world collapse upon realising you can't build your self-worth on the approval of others.

 On that road to self-worth:
 you look for love – and get slut-shamed;
 you work hard – but your output is trivialised as not enough.
 your ambition paints you as unlikeable,
 your joy makes you fake.

So in this darkest of nights for her professionally, she finds the freedom to not needing to constantly internalise the external. She falls in love.
She says: "I wasn't happy in the way I'd been trained to.
It was happiness without anyone else's input".


And so for a generation of girls growing up understanding their only worth as being skinny and gorgeous; and then in the last decade see that world view being unraveled and becoming empowered enough to use our voice to say things and stand up for ourselves isn’t just the story of Taylor, it’s the story of all of us.

Folklore is a remarkable highlight in Swift’s career and makes you think how long it would have taken her to get there if there hadn’t been this quarantine period. This is the first album presented as not being written in the first person, yet I’d be hard pressed to find a more disarming Taylor in her catalogue.

She’s more revealing than ever, finally understanding that the perfectionist facade she’s carried all these years does her more harm than good. As an intrinsically insecure person -her words, not mine- she lays it bare. “I’ve never been a natural, all I do is try try try” reads mirrorball and this is my trying reveals a person that in spite of all her success was always looking for the place where she belonged.

It reminds me of that Roosevelt quote:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again... who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.

That's the story of Taylor, and I think that’s why her fans are so loyal to her. They don’t think she’s perfect or flawless, but they love her for how bold she’s always been, the strength in her vulnerable songs that articulate not just her life but mirror our own in a way we’d never know how to say ourselves. You don’t write a lot of breakup songs if you always do everything perfect.

And it seems she’s finally found her new aim. Her goal was always clearly 1989: a blockbuster pop album, become the biggest celebrity in the world check.
And now, she’s settling into her status as one of the greats.

She’s deploying the incredible savvy that by the age of 30 had made her the highest paid celebrity in the world, to urge the industry to be more fair and also empower younger artists to be more involved in the songwriting process and understand what all these contracts even mean in the first place.

She's inspiring to older professional musicians in her stance against streaming services and exploitative business practices. People not involved in the music industry might not realise what a big deal her re-recordings are, but Paul McCartney doesn't own the Beatles catalogue, Prince had to change his name, and now she, when she didn't consent to her catalogue being sold decides to devalue it in its entirety by creating re-recordings of her work to which to the public sound identical but make grown rockstars shout in awe "damn Taylor. this is better".

It is astonishing.
It has no parallel.
Lawyers and industry professionals are calling it now saying it's changing how contracts in the music industry are structured. Younger, and especially female artists are becoming more involved in the writing process as they've grown up with her and seeing the power that writing her own songs has given her.

What's so remarkable is seeing her transition from this person so desperate for validation becoming an authority using her influence to defend artists who are not accurately accounted for in the dealings between tech companies, music executives, and now most recently anonymous venture funds.

It's profound to see her now, not just displaying confidence but exuding it. It hits different when it so clearly comes from within.

She knows every young female artist looks up to her. She now knows she had to take battles so others didn’t have to. I could argue we wouldn’t have Ariana’s thank u, next without Taylor’s Blank Space, artists like Halsey and Billie Eilish openly stated her as an inspiration, not just artistically but in being the writer of their work.

I can imagine at the time these battles felt really isolating and all she could do was pour her heart and soul into the next album and then the next and then the next. And now we have her, 10 albums in, no longer feeling the need to make music to make a point. She says herself in her Billboard Woman of the Decade acceptance speech:

“and as for me, lately I’ve been focusing less on what they say I can’t do – and more on doing, whatever the hell I want”

and this my friends, is what is with the Taylor Swift thing:
it’s an empire, built on empathy.


Taylor Swift on Ellen with Zac Efron
"One day, I'll be – singing this at the GRAMMYs; and all you're ever gonna be is mean" – Taylor Swift claps back at a journalist who criticised a previous performance of hers (more here
Trailer for the Miss Americana film, released in January 2020
Taylor Swift accepts 'Woman of the Decade'at Billboard in 2019