Our Take: 13 leadership skills that turned Taylor Swift into a $1.6 billion musical icon

Is there a more divisive music artist than Taylor Swift?

On one hand, you have die-hard Swifies that follow her every move and on the other, you have people that think she’s overhyped, overrated and simply just not that good.

But don’t worry, I’m not here to turn you into a mega-fan. But I am here to celebrate some of the leadership traits and skills that Taylor has demonstrated on her rise from small country-town singer to dominate her chosen field as the global icon she is today.

Adaptability

Swifties that were around in 2003 (or that at least know the lyrics to Mary’s Song) will be able to appreciate just how much Taylor’s style has adapted over the years.

From country, to pop, to folk, her albums are known as “eras” for a reason. 

But this doesn’t just reflect a singer that’s inconsistent or indecisive – it actually demonstrates Taylor’s ability to bend and mold to her fans; how they age, what they want; what society is calling for.

The Folklore album is a perfect example of this. Released just after the Covid-19 pandemic, Folklore (and sister album Evermore) are a collection of songs that tell the stories of others; a love triangle, war heroes tales, a murder mystery.

In a time where the world was an uncertain place, Taylor gifted her listeners with two albums that perfectly fit the time. Once more showing her EQ and ability to connect with her fans.

Resilience

Let’s go back to the 2009 VMAs. 

Taylor had just been announced as the winner of the ‘Best Female Video’ award when mid-way through her speech, Kanye West took the microphone and declared that – in his opinion – Beyonce was the more deserved winner.

Met with boos, a disorientated and humiliated Taylor stumbled her way off the stage believing that the audience’s reaction was against her and in solidarity with Kanye.

From this experience, she recalled hearing: “You are not respected here. You shouldn’t be here on this stage,” later admitting that this message “burrowed into my psyche” causing her to “work harder than anyone expects me to”.

Now, she’s the wealthiest female musician in the world, worth an estimated $1.6 billion.

She didn’t give up. And had the courage of her conviction to continue working on new projects, and with new artists.

Be astute

At 15, Taylor signed her first record deal, where she released her first six albums. The rights to these recordings were later sold without her consent to music mogul Scooter Braun.

But why did she make such a fuss about it?

Put simply, it stripped her of financial rights and artistic freedom, while ensuring someone else (Scooter) profited off her life’s work. Another way of looking at it is her work would be passed down the generations of his family, when Taylor wanted to the rights to own her own work.

But rather than accepting defeat, Taylor thought outside of the box to do what no other musician had done before: rerecord her masters. 

Many did not think this would work – after all, how can rereleases of old music be successful? Well, Taylor gave her songs slightly different sounds and artwork, and crucially she branded them “(Taylor’s Version)”.

Now, after the success of the Era’s tour and by rereleasing four of her original albums, she managed to buy back the rights to her entire discography. 

Strategic thinking

If you’re reading this piece, I’m assuming you’ve heard of the Era’s Tour. If not, let’s recap:

• Taylor performed 149 shows in 21 countries
• Sold over 10 million tickets
• Generated a total revenue of ~$2 billion – breaking global sales records

The tour was a sell-out success, mainly because Taylor was able to think carefully and strategically about what her audience wanted.

For example, in the three and a half hour show, Taylor was able to span almost 17 years of music – appealing to both old fans and new.

The tour was also a powerful complement to fans eagerly awaiting the release of rerecorded albums and each night she performed two “surprise” acoustic songs. 

But it also became a cultural moment. Fans were encouraged to dress as their favorite Taylor era, song or character, to trade friendship bracelets and spotting which celebs were in the VIP tent was the greatest sport of summer 2024. 

The Era’s tour excelled not just because of Taylor’s music, but because of how she positioned it as a business venture.

Emotional intelligence

To really connect and understand people, emotional intelligence (EQ) is a must.

Soon after her infamous feud with Kanye West, Taylor disappeared from the public eye for roughly a year – no music, no sightings, nothing.

November 2017 then marked her “revenge” era, otherwise known as Reputation. 

Through the imagery of snakes, graveyards and extravagant wealth, Taylor released a self-reflective album that told her side of the argument, while lacing the album with vulnerable tracks that provided a window into her life.

By leveraging her EQ in this dualled way, Taylor was able to outwardly assert dominance over the narrative while sharing the isolation and fear that her “reputation” had caused – ultimately building a more authentic relationship with her listeners.

Incentives

Taylor rerecording her albums is incredibly significant – and it actually signifies another key attribute that great all leaders need: Incentives.

By going against the grain, attempting what others thought was impossible, and being transparent about her story, Taylor was able to encourage her fans to be selective about which of her music they listened to: Only songs that were given the (Taylor’s Version) label. 

But to encourage this, Taylor knew she had to not only make the concept appealing for fans, but she also had to make listening to the new albums worthwhile.

Cue: Vault tracks.

On every rereleased album, Taylor included a handful of new songs as a ‘thank you’ for listening to her new (old) album.

In other words, by incentivizing fans, Taylor was able to keep fans engaged which lead to the success of her rereleases. 

Integrity

Remember we mentioned Taylor’s feud with Kanye West? 

Well, Kanye’s song Famous includes the line: ‘I made that b***h famous’ – referring to Taylor Swift.

Taylor vehemently denied permitting Kanye to use this line, but he and ex-wife Kim Kardashian leaked an edited tape recording from a phone call, where it appeared that she did give consent. 

This fueled a barrage of online hate, causing Taylor to go into hiding (the Reputation era, just mentioned).

However, later in 2020, the unedited tape leaked, proving her innocence. This showed that even though thousands of people were judging her character, she was able to maintain her integrity. 

Advocacy and inclusivity

In a highly-publicized 2017 trial, Taylor transformed a personal legal challenge into a significant public act of advocacy for women.

The now billionaire earnt a symbolic $1 in damages that delivered a victory for survivors of sexual assault, after former radio host David Mueller sued her for defamation following his termination for groping her. 

By countersuing for just $1, Taylor demonstrated that her motivation was not for financial gain, but rather to stand up for women’s rights while encouraging other women to speak out, too.

Authenticity

Have you heard that Taylor Swift gives her fans “Easter eggs?” 

Small but meaningful clues to not only keep fans engaged, but they demonstrate a unique level of authenticity that symbolize a ‘nod’ to her most devoted fans – an ‘if you know, you know’ clue.

For example, Taylor’s albums are all color coded and the door she left the Era’s tour from was orange – symbolizing her new album, Life of a Showgirl.

To market 1989 (Taylor’s Version) she collaborated with Google to host her Google Vault Puzzle. Fans had to solve 33 million word puzzles to collectively unlock the new track titles.

The Bejewelled music video was also littered with clues, the most poignant being the colors on the elevator buttons, which fans quickly realized were clues as to which albums would be rerecorded next. 

By being authentic and creating these ‘easter eggs’ for fans, Taylor has built a loyal community, while appearing relatable and consistent.

(Also, the Look What You Made Me Do video featured Taylor in a bathtub with a single $1 bill, referencing her iconic win against David Mueller).

Accountability

Everyone makes mistakes (even Taylor Swift) but one of the most important hallmarks of a good leader is that they can recognize their errors.

One way in which Taylor holds herself to account is through her self-reflective songs (yes, they’re not all about break ups).

For example, Twilight movie fans might know how the song Back To December is an apology to ex-boyfriend Taylor Lautner, and Afterglow is a reflective depiction of how poorly she managed a fight.

By publicly airing her flaws, Taylor sends the message of self-awareness and accountability.

Listening

All Too Well (10-minute Version) (Taylor’s Version). 

If you know, you know. If you don’t, then clearly you’ve never been cry-singing in your car to the original heartbreak anthem.

All Too Well was originally released in 2012 with the gut-wrenching theme of unrequited love (until he wanted her back when it was too late – classic).

Fans LOVED it as it was juicy, raw and relatable, so, even though it wasn’t a single, it became a huge hit.

Speaking on this, Taylor said soon after its release: “It originally was like ten minutes long. We cut it down to what you hear now, but I still have that original version.”

And this drove fans into a frenzy, as four minutes of this masterpiece was not enough – they wanted it all.

Nine years later, on her rerecord of her Red album, Taylor showed that not only did she listen to her fans but she was happy to deliver, as she released the full, 10-minute version.

Empathy

Taylor has a long list of philanthropic ventures – dating back from when she was a young country singer, to the global superstar that she is today.

From hosting private meetings with fans going through difficult circumstances, to gifting sizable donations to food banks to every Era’s tour stop, Taylor has ensured she’s continued to offer small but meaningful acts of kindness to those who need it the most.

50 of her production truck drivers were also met with $100,000 bonuses, as a token of her appreciation for hauling her stage and equipment across the US.

Inspirational and relatability

Whether Taylor inspires you because of her music, her public appearances or her business acumen, it’s hard to avoid noticing that she’s achieved some pretty amazing milestones.

By breaking records, entertaining hundreds of thousands of people, and doing what others thought were impossible, Taylor has won the hearts of countless people across the globe.

And even though she’s one of the world’s most famous people, she’s still able to act with integrity and grace, while sharing some of her most vulnerable thoughts and feelings so publicly. 

Now, we can’t all inspire others by standing on stage in a glittery leotard in front of a packed stadium, nor do our businesses have endless $100,000 bonuses to give.

However, by identifying these relatable traits that Taylor Swift has used to help elevate her to success, maybe other business leaders can strive to follow suit in their own way.