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Taylor Swift
1989 - A global mega music icon
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Taylor Swift
Wisdom
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Gratitude
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Leadership
"Believe in everything you do. Believe in your mistakes and grow from them."

My Story

Discussion Questions

Historical Role Models

Related Resources

My Story


Discussion

Questions

Strengths

Historical

Role Models

Related

Resources

Who Am I?

Taylor Swift is an American singer-songwriter, born in Pennsylvania in 1989. She began writing songs as a child and moved to Nashville as a young teenager to chase her dream of becoming a country music star. She signed her first record deal at just 15 years old. Over the next two decades, Taylor grew from a country newcomer into one of the most successful and influential musicians in the world, moving through pop, folk and beyond, while writing almost all of her own songs. She has released more than a dozen studio albums, sold out record-breaking world tours, and won more Grammy Awards than almost any artist in history.

But behind the fame, Taylor faced a serious setback early in her career. When she was young, she signed a contract that meant she didn’t actually own the original recordings of her first six albums, called her “masters”. In 2019, those masters were sold to someone else without her getting the chance to buy them herself. Rather than accept this, Taylor made a bold and patient decision: she would re-record every single album herself, creating brand new versions that she would fully own. It took years of work, and in 2025, she finally succeeded in buying back her original masters too. Today, Taylor owns every song she has ever made, a personal victory achieved through years of careful thought and hard work rather than a quick reaction.

What Am I Known For?

Taylor’s story is a powerful example of wisdom, showing good judgement in making sensible decisions. When she lost her masters, she didn’t react instantly with anger, nor did she simply give up. Instead, she paused, gathered information and thought carefully about her options before choosing the path that would serve her best in the long run, even though it would take years to complete. This is what true wisdom looks like: not always the fastest response, but the most sensible one. Alongside wisdom, Taylor also shows real gratitude. Throughout her career, she has found personal ways to thank the people who support her, hosting small “Secret Sessions” where fans hear new music before anyone else, sending handwritten notes and surprise gifts each year, and even preparing individual gifts for every single member of her touring team at the end of each tour leg. Gratitude, for Taylor, isn’t just a feeling; it’s something she actively builds into how she treats people, whether that’s an audience of thousands or someone working quietly behind the scenes. When she finally regained ownership of her music in 2025, she wrote in a public letter, “All of the music I’ve ever made…now belongs...to me.” Those words capture years of patient decision-making finally paying off, a reminder that wisdom often means playing the long game rather than looking for a quick fix.

Image: iHeartRadioCA, CC BY 3.0, via Wikimedia Commons

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