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Taylor Swift Reflects on 20 Years of Music, “Reputation” and Her Country Roots

After over two decades in the music industry, Taylor Swift is taking a moment to look back at what made her the artist she is today.

Following a whirlwind summer that included a Songwriters Hall of Fame induction, an original song for “Toy Story 5” and her wedding, Swift returned to Los Angeles for a conversation about the career that brought her there in the first place: songwriting.

“The Icon Sessions with Taylor Swift: A 20-Year Retrospective,” presented by the Recording Academy’s Songwriters & Composers Wing, brought Swift to the Grammy Museum earlier this month. Recording Academy CEO Harvey Mason Jr. led the conversation, which covered everything from public scrutiny and her “Reputation” era to her country roots and the lessons she hopes the next generation of songwriters takes from her career.

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Taylor Swift attends the Songwriters Hall of Fame 55th Annual Induction in New York City.

Taylor Swift Says She Chose This Life and Still Chooses It

For Swift, trusting her instincts has never meant expecting everyone to understand her work.

When Mason Jr. asked how she learned to trust herself while releasing music to the world, Swift pointed back to the reason she started making songs in the first place: her fans.

She explained that she makes music for people who turn to it the same way she once did as a way to process life. Once she remembers that purpose, she said, she can separate creating something she loves from the impossible expectation of universal approval.

That mindset has also helped Swift navigate years of commentary about her lyrics. Instead of letting every reaction discourage her, she has learned to turn some of it into inspiration.

“Sometimes when people are mocking me, it’s really fun to mock them back,” she said.

Swift also spoke about the coping mechanisms she has developed throughout her career. One, she explained, involves reminding herself that she chose this life and continues to choose it.

That choice comes with the scrutiny, criticism and pressure that follow her, but Swift said the ability to keep making music makes it worthwhile.

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Taylor Swift attends the 67th Annual GRAMMY Awards in Los Angeles, California.

Swift Reflects on “Reputation,” Re-Records and Her Country Roots

Swift also revisited “Reputation,” an album born from one of the most complicated periods of her public life.

She described the era as “a time in my life when — for the very first time, not the last  people had really actively tried to misunderstand me, just in general, and to misunderstand what I was trying to say and to purposely misinterpret it.”

Looking back, however, Swift feels proud of what came from that period.

“I think the things that I look back on now is when I’ve gone through something that was sort of an attempt to drive me insane,” she said. “When you don’t allow that to happen, and you use art and music as a way to like barrel roll out of that, those are the moments I’m the most proud of.”

Her approach to songwriting has also become more intentional over the years. Swift described herself as a “confessional songwriter,” but she stressed that vulnerability alone does not automatically create meaningful art.

“Not all shocking revelations you make about yourself are deep,” she said. “Just saying something dramatic, shocking and wild doesn’t make it something that’s going to help people, resonate with people, be an important story that sits in people’s minds, hearts and souls.”

For Swift, every detail needs a reason to exist.

“We have to be purposeful,” she said. “Let’s not be haphazard with these things; let’s make them count.”

That philosophy extends to her creative process. Swift said she is “not a big mood board artist” and typically decides on an album’s aesthetics toward the end rather than letting the visuals dictate the music from the beginning.

She also opened up about the uncertainty surrounding her “Taylor’s Version” re-recordings, comparing the experience to having to redo homework after a dog actually ate it.

“At first, it’s like when the dog actually did eat your homework, and you’re like, ‘Now I have to redo it all?’”Swift said.

The public skepticism made the process even more intimidating, but Swift ultimately pushed forward with the project despite doubts that fans would embrace new versions of songs they already knew.

And while her career has taken her far beyond her early Nashville days, Swift said she feels increasingly connected to where it all began. “I love my country roots more and more the further along this path I get,” she said. “I want to honor them more and more.”

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Taylor Swift announces nominees for the 2007 CMA Awards on August 30, 2007 in Nashville, Tennessee.

For the young songwriters listening, Swift offered one final piece of advice: “I hope that you will show up to work even when the idea fairy doesn’t.” She encouraged them to build on each other’s ideas, remember the ‘yes, and’ mentality of improv and, most importantly, hold onto their enthusiasm.

“In the music industry, as wild and ever-changing as it is, enthusiasm can protect you from anything,” Swift said. “I would know.”

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